diff --git a/Cargo.lock b/Cargo.lock
index 45a313a72b..74cd2c8d2c 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4436,6 +4436,7 @@ dependencies = [
  "futures",
  "futures-util",
  "http-types",
+ "humantime",
  "hyper",
  "itertools",
  "metrics",
@@ -4447,6 +4448,7 @@ dependencies = [
  "serde_json",
  "test-context",
  "tokio",
+ "tokio-stream",
  "tokio-util",
  "toml_edit",
  "tracing",
diff --git a/libs/remote_storage/Cargo.toml b/libs/remote_storage/Cargo.toml
index 2cc59a947b..15f3cd3b80 100644
--- a/libs/remote_storage/Cargo.toml
+++ b/libs/remote_storage/Cargo.toml
@@ -15,11 +15,13 @@ aws-sdk-s3.workspace = true
 aws-credential-types.workspace = true
 bytes.workspace = true
 camino.workspace = true
+humantime.workspace = true
 hyper = { workspace = true, features = ["stream"] }
 futures.workspace = true
 serde.workspace = true
 serde_json.workspace = true
 tokio = { workspace = true, features = ["sync", "fs", "io-util"] }
+tokio-stream.workspace = true
 tokio-util = { workspace = true, features = ["compat"] }
 toml_edit.workspace = true
 tracing.workspace = true
diff --git a/libs/remote_storage/src/azure_blob.rs b/libs/remote_storage/src/azure_blob.rs
index df6d45dde1..12ec680cb6 100644
--- a/libs/remote_storage/src/azure_blob.rs
+++ b/libs/remote_storage/src/azure_blob.rs
@@ -22,16 +22,15 @@ use azure_storage_blobs::{blob::operations::GetBlobBuilder, prelude::ContainerCl
 use bytes::Bytes;
 use futures::stream::Stream;
 use futures_util::StreamExt;
+use futures_util::TryStreamExt;
 use http_types::{StatusCode, Url};
-use tokio::time::Instant;
 use tokio_util::sync::CancellationToken;
 use tracing::debug;
 
-use crate::s3_bucket::RequestKind;
-use crate::TimeTravelError;
 use crate::{
-    AzureConfig, ConcurrencyLimiter, Download, DownloadError, Listing, ListingMode, RemotePath,
-    RemoteStorage, StorageMetadata,
+    error::Cancelled, s3_bucket::RequestKind, AzureConfig, ConcurrencyLimiter, Download,
+    DownloadError, Listing, ListingMode, RemotePath, RemoteStorage, StorageMetadata,
+    TimeTravelError, TimeoutOrCancel,
 };
 
 pub struct AzureBlobStorage {
@@ -39,10 +38,12 @@ pub struct AzureBlobStorage {
     prefix_in_container: Option<String>,
     max_keys_per_list_response: Option<NonZeroU32>,
     concurrency_limiter: ConcurrencyLimiter,
+    // Per-request timeout. Accessible for tests.
+    pub timeout: Duration,
 }
 
 impl AzureBlobStorage {
-    pub fn new(azure_config: &AzureConfig) -> Result<Self> {
+    pub fn new(azure_config: &AzureConfig, timeout: Duration) -> Result<Self> {
         debug!(
             "Creating azure remote storage for azure container {}",
             azure_config.container_name
@@ -79,6 +80,7 @@ impl AzureBlobStorage {
             prefix_in_container: azure_config.prefix_in_container.to_owned(),
             max_keys_per_list_response,
             concurrency_limiter: ConcurrencyLimiter::new(azure_config.concurrency_limit.get()),
+            timeout,
         })
     }
 
@@ -121,8 +123,11 @@ impl AzureBlobStorage {
     async fn download_for_builder(
         &self,
         builder: GetBlobBuilder,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
-        let mut response = builder.into_stream();
+        let kind = RequestKind::Get;
+
+        let _permit = self.permit(kind, cancel).await?;
 
         let mut etag = None;
         let mut last_modified = None;
@@ -130,39 +135,70 @@ impl AzureBlobStorage {
         // TODO give proper streaming response instead of buffering into RAM
         // https://github.com/neondatabase/neon/issues/5563
 
-        let mut bufs = Vec::new();
-        while let Some(part) = response.next().await {
-            let part = part.map_err(to_download_error)?;
-            let etag_str: &str = part.blob.properties.etag.as_ref();
-            if etag.is_none() {
-                etag = Some(etag.unwrap_or_else(|| etag_str.to_owned()));
+        let download = async {
+            let response = builder
+                // convert to concrete Pageable
+                .into_stream()
+                // convert to TryStream
+                .into_stream()
+                .map_err(to_download_error);
+
+            // apply per request timeout
+            let response = tokio_stream::StreamExt::timeout(response, self.timeout);
+
+            // flatten
+            let response = response.map(|res| match res {
+                Ok(res) => res,
+                Err(_elapsed) => Err(DownloadError::Timeout),
+            });
+
+            let mut response = std::pin::pin!(response);
+
+            let mut bufs = Vec::new();
+            while let Some(part) = response.next().await {
+                let part = part?;
+                let etag_str: &str = part.blob.properties.etag.as_ref();
+                if etag.is_none() {
+                    etag = Some(etag.unwrap_or_else(|| etag_str.to_owned()));
+                }
+                if last_modified.is_none() {
+                    last_modified = Some(part.blob.properties.last_modified.into());
+                }
+                if let Some(blob_meta) = part.blob.metadata {
+                    metadata.extend(blob_meta.iter().map(|(k, v)| (k.to_owned(), v.to_owned())));
+                }
+                let data = part
+                    .data
+                    .collect()
+                    .await
+                    .map_err(|e| DownloadError::Other(e.into()))?;
+                bufs.push(data);
             }
-            if last_modified.is_none() {
-                last_modified = Some(part.blob.properties.last_modified.into());
-            }
-            if let Some(blob_meta) = part.blob.metadata {
-                metadata.extend(blob_meta.iter().map(|(k, v)| (k.to_owned(), v.to_owned())));
-            }
-            let data = part
-                .data
-                .collect()
-                .await
-                .map_err(|e| DownloadError::Other(e.into()))?;
-            bufs.push(data);
+            Ok(Download {
+                download_stream: Box::pin(futures::stream::iter(bufs.into_iter().map(Ok))),
+                etag,
+                last_modified,
+                metadata: Some(StorageMetadata(metadata)),
+            })
+        };
+
+        tokio::select! {
+            bufs = download => bufs,
+            _ = cancel.cancelled() => Err(DownloadError::Cancelled),
         }
-        Ok(Download {
-            download_stream: Box::pin(futures::stream::iter(bufs.into_iter().map(Ok))),
-            etag,
-            last_modified,
-            metadata: Some(StorageMetadata(metadata)),
-        })
     }
 
-    async fn permit(&self, kind: RequestKind) -> tokio::sync::SemaphorePermit<'_> {
-        self.concurrency_limiter
-            .acquire(kind)
-            .await
-            .expect("semaphore is never closed")
+    async fn permit(
+        &self,
+        kind: RequestKind,
+        cancel: &CancellationToken,
+    ) -> Result<tokio::sync::SemaphorePermit<'_>, Cancelled> {
+        let acquire = self.concurrency_limiter.acquire(kind);
+
+        tokio::select! {
+            permit = acquire => Ok(permit.expect("never closed")),
+            _ = cancel.cancelled() => Err(Cancelled),
+        }
     }
 }
 
@@ -192,66 +228,87 @@ impl RemoteStorage for AzureBlobStorage {
         prefix: Option<&RemotePath>,
         mode: ListingMode,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<Listing, DownloadError> {
-        // get the passed prefix or if it is not set use prefix_in_bucket value
-        let list_prefix = prefix
-            .map(|p| self.relative_path_to_name(p))
-            .or_else(|| self.prefix_in_container.clone())
-            .map(|mut p| {
-                // required to end with a separator
-                // otherwise request will return only the entry of a prefix
-                if matches!(mode, ListingMode::WithDelimiter)
-                    && !p.ends_with(REMOTE_STORAGE_PREFIX_SEPARATOR)
-                {
-                    p.push(REMOTE_STORAGE_PREFIX_SEPARATOR);
-                }
-                p
+        let _permit = self.permit(RequestKind::List, cancel).await?;
+
+        let op = async {
+            // get the passed prefix or if it is not set use prefix_in_bucket value
+            let list_prefix = prefix
+                .map(|p| self.relative_path_to_name(p))
+                .or_else(|| self.prefix_in_container.clone())
+                .map(|mut p| {
+                    // required to end with a separator
+                    // otherwise request will return only the entry of a prefix
+                    if matches!(mode, ListingMode::WithDelimiter)
+                        && !p.ends_with(REMOTE_STORAGE_PREFIX_SEPARATOR)
+                    {
+                        p.push(REMOTE_STORAGE_PREFIX_SEPARATOR);
+                    }
+                    p
+                });
+
+            let mut builder = self.client.list_blobs();
+
+            if let ListingMode::WithDelimiter = mode {
+                builder = builder.delimiter(REMOTE_STORAGE_PREFIX_SEPARATOR.to_string());
+            }
+
+            if let Some(prefix) = list_prefix {
+                builder = builder.prefix(Cow::from(prefix.to_owned()));
+            }
+
+            if let Some(limit) = self.max_keys_per_list_response {
+                builder = builder.max_results(MaxResults::new(limit));
+            }
+
+            let response = builder.into_stream();
+            let response = response.into_stream().map_err(to_download_error);
+            let response = tokio_stream::StreamExt::timeout(response, self.timeout);
+            let response = response.map(|res| match res {
+                Ok(res) => res,
+                Err(_elapsed) => Err(DownloadError::Timeout),
             });
 
-        let mut builder = self.client.list_blobs();
+            let mut response = std::pin::pin!(response);
 
-        if let ListingMode::WithDelimiter = mode {
-            builder = builder.delimiter(REMOTE_STORAGE_PREFIX_SEPARATOR.to_string());
-        }
+            let mut res = Listing::default();
 
-        if let Some(prefix) = list_prefix {
-            builder = builder.prefix(Cow::from(prefix.to_owned()));
-        }
+            let mut max_keys = max_keys.map(|mk| mk.get());
+            while let Some(entry) = response.next().await {
+                let entry = entry?;
+                let prefix_iter = entry
+                    .blobs
+                    .prefixes()
+                    .map(|prefix| self.name_to_relative_path(&prefix.name));
+                res.prefixes.extend(prefix_iter);
 
-        if let Some(limit) = self.max_keys_per_list_response {
-            builder = builder.max_results(MaxResults::new(limit));
-        }
+                let blob_iter = entry
+                    .blobs
+                    .blobs()
+                    .map(|k| self.name_to_relative_path(&k.name));
 
-        let mut response = builder.into_stream();
-        let mut res = Listing::default();
-        // NonZeroU32 doesn't support subtraction apparently
-        let mut max_keys = max_keys.map(|mk| mk.get());
-        while let Some(l) = response.next().await {
-            let entry = l.map_err(to_download_error)?;
-            let prefix_iter = entry
-                .blobs
-                .prefixes()
-                .map(|prefix| self.name_to_relative_path(&prefix.name));
-            res.prefixes.extend(prefix_iter);
+                for key in blob_iter {
+                    res.keys.push(key);
 
-            let blob_iter = entry
-                .blobs
-                .blobs()
-                .map(|k| self.name_to_relative_path(&k.name));
-
-            for key in blob_iter {
-                res.keys.push(key);
-                if let Some(mut mk) = max_keys {
-                    assert!(mk > 0);
-                    mk -= 1;
-                    if mk == 0 {
-                        return Ok(res); // limit reached
+                    if let Some(mut mk) = max_keys {
+                        assert!(mk > 0);
+                        mk -= 1;
+                        if mk == 0 {
+                            return Ok(res); // limit reached
+                        }
+                        max_keys = Some(mk);
                     }
-                    max_keys = Some(mk);
                 }
             }
+
+            Ok(res)
+        };
+
+        tokio::select! {
+            res = op => res,
+            _ = cancel.cancelled() => Err(DownloadError::Cancelled),
         }
-        Ok(res)
     }
 
     async fn upload(
@@ -260,35 +317,52 @@ impl RemoteStorage for AzureBlobStorage {
         data_size_bytes: usize,
         to: &RemotePath,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
-        let _permit = self.permit(RequestKind::Put).await;
-        let blob_client = self.client.blob_client(self.relative_path_to_name(to));
+        let _permit = self.permit(RequestKind::Put, cancel).await?;
 
-        let from: Pin<Box<dyn Stream<Item = std::io::Result<Bytes>> + Send + Sync + 'static>> =
-            Box::pin(from);
+        let op = async {
+            let blob_client = self.client.blob_client(self.relative_path_to_name(to));
 
-        let from = NonSeekableStream::new(from, data_size_bytes);
+            let from: Pin<Box<dyn Stream<Item = std::io::Result<Bytes>> + Send + Sync + 'static>> =
+                Box::pin(from);
 
-        let body = azure_core::Body::SeekableStream(Box::new(from));
+            let from = NonSeekableStream::new(from, data_size_bytes);
 
-        let mut builder = blob_client.put_block_blob(body);
+            let body = azure_core::Body::SeekableStream(Box::new(from));
 
-        if let Some(metadata) = metadata {
-            builder = builder.metadata(to_azure_metadata(metadata));
+            let mut builder = blob_client.put_block_blob(body);
+
+            if let Some(metadata) = metadata {
+                builder = builder.metadata(to_azure_metadata(metadata));
+            }
+
+            let fut = builder.into_future();
+            let fut = tokio::time::timeout(self.timeout, fut);
+
+            match fut.await {
+                Ok(Ok(_response)) => Ok(()),
+                Ok(Err(azure)) => Err(azure.into()),
+                Err(_timeout) => Err(TimeoutOrCancel::Cancel.into()),
+            }
+        };
+
+        tokio::select! {
+            res = op => res,
+            _ = cancel.cancelled() => Err(TimeoutOrCancel::Cancel.into()),
         }
-
-        let _response = builder.into_future().await?;
-
-        Ok(())
     }
 
-    async fn download(&self, from: &RemotePath) -> Result<Download, DownloadError> {
-        let _permit = self.permit(RequestKind::Get).await;
+    async fn download(
+        &self,
+        from: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError> {
         let blob_client = self.client.blob_client(self.relative_path_to_name(from));
 
         let builder = blob_client.get();
 
-        self.download_for_builder(builder).await
+        self.download_for_builder(builder, cancel).await
     }
 
     async fn download_byte_range(
@@ -296,8 +370,8 @@ impl RemoteStorage for AzureBlobStorage {
         from: &RemotePath,
         start_inclusive: u64,
         end_exclusive: Option<u64>,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
-        let _permit = self.permit(RequestKind::Get).await;
         let blob_client = self.client.blob_client(self.relative_path_to_name(from));
 
         let mut builder = blob_client.get();
@@ -309,82 +383,113 @@ impl RemoteStorage for AzureBlobStorage {
         };
         builder = builder.range(range);
 
-        self.download_for_builder(builder).await
+        self.download_for_builder(builder, cancel).await
     }
 
-    async fn delete(&self, path: &RemotePath) -> anyhow::Result<()> {
-        let _permit = self.permit(RequestKind::Delete).await;
-        let blob_client = self.client.blob_client(self.relative_path_to_name(path));
+    async fn delete(&self, path: &RemotePath, cancel: &CancellationToken) -> anyhow::Result<()> {
+        self.delete_objects(std::array::from_ref(path), cancel)
+            .await
+    }
 
-        let builder = blob_client.delete();
+    async fn delete_objects<'a>(
+        &self,
+        paths: &'a [RemotePath],
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
+        let _permit = self.permit(RequestKind::Delete, cancel).await?;
 
-        match builder.into_future().await {
-            Ok(_response) => Ok(()),
-            Err(e) => {
-                if let Some(http_err) = e.as_http_error() {
-                    if http_err.status() == StatusCode::NotFound {
-                        return Ok(());
+        let op = async {
+            // TODO batch requests are also not supported by the SDK
+            // https://github.com/Azure/azure-sdk-for-rust/issues/1068
+            // https://github.com/Azure/azure-sdk-for-rust/issues/1249
+            for path in paths {
+                let blob_client = self.client.blob_client(self.relative_path_to_name(path));
+
+                let request = blob_client.delete().into_future();
+
+                let res = tokio::time::timeout(self.timeout, request).await;
+
+                match res {
+                    Ok(Ok(_response)) => continue,
+                    Ok(Err(e)) => {
+                        if let Some(http_err) = e.as_http_error() {
+                            if http_err.status() == StatusCode::NotFound {
+                                continue;
+                            }
+                        }
+                        return Err(e.into());
                     }
+                    Err(_elapsed) => return Err(TimeoutOrCancel::Timeout.into()),
                 }
-                Err(anyhow::Error::new(e))
             }
+
+            Ok(())
+        };
+
+        tokio::select! {
+            res = op => res,
+            _ = cancel.cancelled() => Err(TimeoutOrCancel::Cancel.into()),
         }
     }
 
-    async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()> {
-        // Permit is already obtained by inner delete function
+    async fn copy(
+        &self,
+        from: &RemotePath,
+        to: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
+        let _permit = self.permit(RequestKind::Copy, cancel).await?;
 
-        // TODO batch requests are also not supported by the SDK
-        // https://github.com/Azure/azure-sdk-for-rust/issues/1068
-        // https://github.com/Azure/azure-sdk-for-rust/issues/1249
-        for path in paths {
-            self.delete(path).await?;
-        }
-        Ok(())
-    }
+        let timeout = tokio::time::sleep(self.timeout);
 
-    async fn copy(&self, from: &RemotePath, to: &RemotePath) -> anyhow::Result<()> {
-        let _permit = self.permit(RequestKind::Copy).await;
-        let blob_client = self.client.blob_client(self.relative_path_to_name(to));
+        let mut copy_status = None;
 
-        let source_url = format!(
-            "{}/{}",
-            self.client.url()?,
-            self.relative_path_to_name(from)
-        );
-        let builder = blob_client.copy(Url::from_str(&source_url)?);
+        let op = async {
+            let blob_client = self.client.blob_client(self.relative_path_to_name(to));
 
-        let result = builder.into_future().await?;
+            let source_url = format!(
+                "{}/{}",
+                self.client.url()?,
+                self.relative_path_to_name(from)
+            );
 
-        let mut copy_status = result.copy_status;
-        let start_time = Instant::now();
-        const MAX_WAIT_TIME: Duration = Duration::from_secs(60);
-        loop {
-            match copy_status {
-                CopyStatus::Aborted => {
-                    anyhow::bail!("Received abort for copy from {from} to {to}.");
+            let builder = blob_client.copy(Url::from_str(&source_url)?);
+            let copy = builder.into_future();
+
+            let result = copy.await?;
+
+            copy_status = Some(result.copy_status);
+            loop {
+                match copy_status.as_ref().expect("we always set it to Some") {
+                    CopyStatus::Aborted => {
+                        anyhow::bail!("Received abort for copy from {from} to {to}.");
+                    }
+                    CopyStatus::Failed => {
+                        anyhow::bail!("Received failure response for copy from {from} to {to}.");
+                    }
+                    CopyStatus::Success => return Ok(()),
+                    CopyStatus::Pending => (),
                 }
-                CopyStatus::Failed => {
-                    anyhow::bail!("Received failure response for copy from {from} to {to}.");
-                }
-                CopyStatus::Success => return Ok(()),
-                CopyStatus::Pending => (),
+                // The copy is taking longer. Waiting a second and then re-trying.
+                // TODO estimate time based on copy_progress and adjust time based on that
+                tokio::time::sleep(Duration::from_millis(1000)).await;
+                let properties = blob_client.get_properties().into_future().await?;
+                let Some(status) = properties.blob.properties.copy_status else {
+                    tracing::warn!("copy_status for copy is None!, from={from}, to={to}");
+                    return Ok(());
+                };
+                copy_status = Some(status);
             }
-            // The copy is taking longer. Waiting a second and then re-trying.
-            // TODO estimate time based on copy_progress and adjust time based on that
-            tokio::time::sleep(Duration::from_millis(1000)).await;
-            let properties = blob_client.get_properties().into_future().await?;
-            let Some(status) = properties.blob.properties.copy_status else {
-                tracing::warn!("copy_status for copy is None!, from={from}, to={to}");
-                return Ok(());
-            };
-            if start_time.elapsed() > MAX_WAIT_TIME {
-                anyhow::bail!("Copy from from {from} to {to} took longer than limit MAX_WAIT_TIME={}s. copy_pogress={:?}.",
-                    MAX_WAIT_TIME.as_secs_f32(),
-                    properties.blob.properties.copy_progress,
-                );
-            }
-            copy_status = status;
+        };
+
+        tokio::select! {
+            res = op => res,
+            _ = cancel.cancelled() => Err(anyhow::Error::new(TimeoutOrCancel::Cancel)),
+            _ = timeout => {
+                let e = anyhow::Error::new(TimeoutOrCancel::Timeout);
+                let e = e.context(format!("Timeout, last status: {copy_status:?}"));
+                Err(e)
+            },
         }
     }
 
diff --git a/libs/remote_storage/src/error.rs b/libs/remote_storage/src/error.rs
new file mode 100644
index 0000000000..96f044e087
--- /dev/null
+++ b/libs/remote_storage/src/error.rs
@@ -0,0 +1,181 @@
+/// Reasons for downloads or listings to fail.
+#[derive(Debug)]
+pub enum DownloadError {
+    /// Validation or other error happened due to user input.
+    BadInput(anyhow::Error),
+    /// The file was not found in the remote storage.
+    NotFound,
+    /// A cancellation token aborted the download, typically during
+    /// tenant detach or process shutdown.
+    Cancelled,
+    /// A timeout happened while executing the request. Possible reasons:
+    /// - stuck tcp connection
+    ///
+    /// Concurrency control is not timed within timeout.
+    Timeout,
+    /// The file was found in the remote storage, but the download failed.
+    Other(anyhow::Error),
+}
+
+impl std::fmt::Display for DownloadError {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            DownloadError::BadInput(e) => {
+                write!(f, "Failed to download a remote file due to user input: {e}")
+            }
+            DownloadError::NotFound => write!(f, "No file found for the remote object id given"),
+            DownloadError::Cancelled => write!(f, "Cancelled, shutting down"),
+            DownloadError::Timeout => write!(f, "timeout"),
+            DownloadError::Other(e) => write!(f, "Failed to download a remote file: {e:?}"),
+        }
+    }
+}
+
+impl std::error::Error for DownloadError {}
+
+impl DownloadError {
+    /// Returns true if the error should not be retried with backoff
+    pub fn is_permanent(&self) -> bool {
+        use DownloadError::*;
+        match self {
+            BadInput(_) | NotFound | Cancelled => true,
+            Timeout | Other(_) => false,
+        }
+    }
+}
+
+#[derive(Debug)]
+pub enum TimeTravelError {
+    /// Validation or other error happened due to user input.
+    BadInput(anyhow::Error),
+    /// The used remote storage does not have time travel recovery implemented
+    Unimplemented,
+    /// The number of versions/deletion markers is above our limit.
+    TooManyVersions,
+    /// A cancellation token aborted the process, typically during
+    /// request closure or process shutdown.
+    Cancelled,
+    /// Other errors
+    Other(anyhow::Error),
+}
+
+impl std::fmt::Display for TimeTravelError {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            TimeTravelError::BadInput(e) => {
+                write!(
+                    f,
+                    "Failed to time travel recover a prefix due to user input: {e}"
+                )
+            }
+            TimeTravelError::Unimplemented => write!(
+                f,
+                "time travel recovery is not implemented for the current storage backend"
+            ),
+            TimeTravelError::Cancelled => write!(f, "Cancelled, shutting down"),
+            TimeTravelError::TooManyVersions => {
+                write!(f, "Number of versions/delete markers above limit")
+            }
+            TimeTravelError::Other(e) => write!(f, "Failed to time travel recover a prefix: {e:?}"),
+        }
+    }
+}
+
+impl std::error::Error for TimeTravelError {}
+
+/// Plain cancelled error.
+///
+/// By design this type does not not implement `std::error::Error` so it cannot be put as the root
+/// cause of `std::io::Error` or `anyhow::Error`. It should never need to be exposed out of this
+/// crate.
+///
+/// It exists to implement permit acquiring in `{Download,TimeTravel}Error` and `anyhow::Error` returning
+/// operations and ensuring that those get converted to proper versions with just `?`.
+#[derive(Debug)]
+pub(crate) struct Cancelled;
+
+impl From<Cancelled> for anyhow::Error {
+    fn from(_: Cancelled) -> Self {
+        anyhow::Error::new(TimeoutOrCancel::Cancel)
+    }
+}
+
+impl From<Cancelled> for TimeTravelError {
+    fn from(_: Cancelled) -> Self {
+        TimeTravelError::Cancelled
+    }
+}
+
+impl From<Cancelled> for TimeoutOrCancel {
+    fn from(_: Cancelled) -> Self {
+        TimeoutOrCancel::Cancel
+    }
+}
+
+impl From<Cancelled> for DownloadError {
+    fn from(_: Cancelled) -> Self {
+        DownloadError::Cancelled
+    }
+}
+
+/// This type is used at as the root cause for timeouts and cancellations with `anyhow::Error` returning
+/// RemoteStorage methods.
+///
+/// For use with `utils::backoff::retry` and `anyhow::Error` returning operations there is
+/// `TimeoutOrCancel::caused_by_cancel` method to query "proper form" errors.
+#[derive(Debug)]
+pub enum TimeoutOrCancel {
+    Timeout,
+    Cancel,
+}
+
+impl std::fmt::Display for TimeoutOrCancel {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        use TimeoutOrCancel::*;
+        match self {
+            Timeout => write!(f, "timeout"),
+            Cancel => write!(f, "cancel"),
+        }
+    }
+}
+
+impl std::error::Error for TimeoutOrCancel {}
+
+impl TimeoutOrCancel {
+    pub fn caused(error: &anyhow::Error) -> Option<&Self> {
+        error.root_cause().downcast_ref()
+    }
+
+    /// Returns true if the error was caused by [`TimeoutOrCancel::Cancel`].
+    pub fn caused_by_cancel(error: &anyhow::Error) -> bool {
+        Self::caused(error).is_some_and(Self::is_cancel)
+    }
+
+    pub fn is_cancel(&self) -> bool {
+        matches!(self, TimeoutOrCancel::Cancel)
+    }
+
+    pub fn is_timeout(&self) -> bool {
+        matches!(self, TimeoutOrCancel::Timeout)
+    }
+}
+
+/// This conversion is used when [`crate::support::DownloadStream`] notices a cancellation or
+/// timeout to wrap it in an `std::io::Error`.
+impl From<TimeoutOrCancel> for std::io::Error {
+    fn from(value: TimeoutOrCancel) -> Self {
+        let e = DownloadError::from(value);
+        std::io::Error::other(e)
+    }
+}
+
+impl From<TimeoutOrCancel> for DownloadError {
+    fn from(value: TimeoutOrCancel) -> Self {
+        use TimeoutOrCancel::*;
+
+        match value {
+            Timeout => DownloadError::Timeout,
+            Cancel => DownloadError::Cancelled,
+        }
+    }
+}
diff --git a/libs/remote_storage/src/lib.rs b/libs/remote_storage/src/lib.rs
index 5a0b74e406..b0b69f9155 100644
--- a/libs/remote_storage/src/lib.rs
+++ b/libs/remote_storage/src/lib.rs
@@ -10,6 +10,7 @@
 #![deny(clippy::undocumented_unsafe_blocks)]
 
 mod azure_blob;
+mod error;
 mod local_fs;
 mod s3_bucket;
 mod simulate_failures;
@@ -21,7 +22,7 @@ use std::{
     num::{NonZeroU32, NonZeroUsize},
     pin::Pin,
     sync::Arc,
-    time::SystemTime,
+    time::{Duration, SystemTime},
 };
 
 use anyhow::{bail, Context};
@@ -41,6 +42,8 @@ pub use self::{
 };
 use s3_bucket::RequestKind;
 
+pub use error::{DownloadError, TimeTravelError, TimeoutOrCancel};
+
 /// Currently, sync happens with AWS S3, that has two limits on requests per second:
 /// ~200 RPS for IAM services
 /// <https://docs.aws.amazon.com/AmazonRDS/latest/AuroraUserGuide/UsingWithRDS.IAMDBAuth.html>
@@ -158,9 +161,10 @@ pub trait RemoteStorage: Send + Sync + 'static {
     async fn list_prefixes(
         &self,
         prefix: Option<&RemotePath>,
+        cancel: &CancellationToken,
     ) -> Result<Vec<RemotePath>, DownloadError> {
         let result = self
-            .list(prefix, ListingMode::WithDelimiter, None)
+            .list(prefix, ListingMode::WithDelimiter, None, cancel)
             .await?
             .prefixes;
         Ok(result)
@@ -182,9 +186,10 @@ pub trait RemoteStorage: Send + Sync + 'static {
         &self,
         prefix: Option<&RemotePath>,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> Result<Vec<RemotePath>, DownloadError> {
         let result = self
-            .list(prefix, ListingMode::NoDelimiter, max_keys)
+            .list(prefix, ListingMode::NoDelimiter, max_keys, cancel)
             .await?
             .keys;
         Ok(result)
@@ -195,9 +200,13 @@ pub trait RemoteStorage: Send + Sync + 'static {
         prefix: Option<&RemotePath>,
         _mode: ListingMode,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> Result<Listing, DownloadError>;
 
     /// Streams the local file contents into remote into the remote storage entry.
+    ///
+    /// If the operation fails because of timeout or cancellation, the root cause of the error will be
+    /// set to `TimeoutOrCancel`.
     async fn upload(
         &self,
         from: impl Stream<Item = std::io::Result<Bytes>> + Send + Sync + 'static,
@@ -206,27 +215,61 @@ pub trait RemoteStorage: Send + Sync + 'static {
         data_size_bytes: usize,
         to: &RemotePath,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()>;
 
-    /// Streams the remote storage entry contents into the buffered writer given, returns the filled writer.
+    /// Streams the remote storage entry contents.
+    ///
+    /// The returned download stream will obey initial timeout and cancellation signal by erroring
+    /// on whichever happens first. Only one of the reasons will fail the stream, which is usually
+    /// enough for `tokio::io::copy_buf` usage. If needed the error can be filtered out.
+    ///
     /// Returns the metadata, if any was stored with the file previously.
-    async fn download(&self, from: &RemotePath) -> Result<Download, DownloadError>;
+    async fn download(
+        &self,
+        from: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError>;
 
-    /// Streams a given byte range of the remote storage entry contents into the buffered writer given, returns the filled writer.
+    /// Streams a given byte range of the remote storage entry contents.
+    ///
+    /// The returned download stream will obey initial timeout and cancellation signal by erroring
+    /// on whichever happens first. Only one of the reasons will fail the stream, which is usually
+    /// enough for `tokio::io::copy_buf` usage. If needed the error can be filtered out.
+    ///
     /// Returns the metadata, if any was stored with the file previously.
     async fn download_byte_range(
         &self,
         from: &RemotePath,
         start_inclusive: u64,
         end_exclusive: Option<u64>,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError>;
 
-    async fn delete(&self, path: &RemotePath) -> anyhow::Result<()>;
+    /// Delete a single path from remote storage.
+    ///
+    /// If the operation fails because of timeout or cancellation, the root cause of the error will be
+    /// set to `TimeoutOrCancel`. In such situation it is unknown if the deletion went through.
+    async fn delete(&self, path: &RemotePath, cancel: &CancellationToken) -> anyhow::Result<()>;
 
-    async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()>;
+    /// Delete a multiple paths from remote storage.
+    ///
+    /// If the operation fails because of timeout or cancellation, the root cause of the error will be
+    /// set to `TimeoutOrCancel`. In such situation it is unknown which deletions, if any, went
+    /// through.
+    async fn delete_objects<'a>(
+        &self,
+        paths: &'a [RemotePath],
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()>;
 
     /// Copy a remote object inside a bucket from one path to another.
-    async fn copy(&self, from: &RemotePath, to: &RemotePath) -> anyhow::Result<()>;
+    async fn copy(
+        &self,
+        from: &RemotePath,
+        to: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()>;
 
     /// Resets the content of everything with the given prefix to the given state
     async fn time_travel_recover(
@@ -238,7 +281,13 @@ pub trait RemoteStorage: Send + Sync + 'static {
     ) -> Result<(), TimeTravelError>;
 }
 
-pub type DownloadStream = Pin<Box<dyn Stream<Item = std::io::Result<Bytes>> + Unpin + Send + Sync>>;
+/// DownloadStream is sensitive to the timeout and cancellation used with the original
+/// [`RemoteStorage::download`] request. The type yields `std::io::Result<Bytes>` to be compatible
+/// with `tokio::io::copy_buf`.
+// This has 'static because safekeepers do not use cancellation tokens (yet)
+pub type DownloadStream =
+    Pin<Box<dyn Stream<Item = std::io::Result<Bytes>> + Send + Sync + 'static>>;
+
 pub struct Download {
     pub download_stream: DownloadStream,
     /// The last time the file was modified (`last-modified` HTTP header)
@@ -257,86 +306,6 @@ impl Debug for Download {
     }
 }
 
-#[derive(Debug)]
-pub enum DownloadError {
-    /// Validation or other error happened due to user input.
-    BadInput(anyhow::Error),
-    /// The file was not found in the remote storage.
-    NotFound,
-    /// A cancellation token aborted the download, typically during
-    /// tenant detach or process shutdown.
-    Cancelled,
-    /// The file was found in the remote storage, but the download failed.
-    Other(anyhow::Error),
-}
-
-impl std::fmt::Display for DownloadError {
-    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        match self {
-            DownloadError::BadInput(e) => {
-                write!(f, "Failed to download a remote file due to user input: {e}")
-            }
-            DownloadError::Cancelled => write!(f, "Cancelled, shutting down"),
-            DownloadError::NotFound => write!(f, "No file found for the remote object id given"),
-            DownloadError::Other(e) => write!(f, "Failed to download a remote file: {e:?}"),
-        }
-    }
-}
-
-impl std::error::Error for DownloadError {}
-
-impl DownloadError {
-    /// Returns true if the error should not be retried with backoff
-    pub fn is_permanent(&self) -> bool {
-        use DownloadError::*;
-        match self {
-            BadInput(_) => true,
-            NotFound => true,
-            Cancelled => true,
-            Other(_) => false,
-        }
-    }
-}
-
-#[derive(Debug)]
-pub enum TimeTravelError {
-    /// Validation or other error happened due to user input.
-    BadInput(anyhow::Error),
-    /// The used remote storage does not have time travel recovery implemented
-    Unimplemented,
-    /// The number of versions/deletion markers is above our limit.
-    TooManyVersions,
-    /// A cancellation token aborted the process, typically during
-    /// request closure or process shutdown.
-    Cancelled,
-    /// Other errors
-    Other(anyhow::Error),
-}
-
-impl std::fmt::Display for TimeTravelError {
-    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        match self {
-            TimeTravelError::BadInput(e) => {
-                write!(
-                    f,
-                    "Failed to time travel recover a prefix due to user input: {e}"
-                )
-            }
-            TimeTravelError::Unimplemented => write!(
-                f,
-                "time travel recovery is not implemented for the current storage backend"
-            ),
-            TimeTravelError::Cancelled => write!(f, "Cancelled, shutting down"),
-            TimeTravelError::TooManyVersions => {
-                write!(f, "Number of versions/delete markers above limit")
-            }
-            TimeTravelError::Other(e) => write!(f, "Failed to time travel recover a prefix: {e:?}"),
-        }
-    }
-}
-
-impl std::error::Error for TimeTravelError {}
-
 /// Every storage, currently supported.
 /// Serves as a simple way to pass around the [`RemoteStorage`] without dealing with generics.
 #[derive(Clone)]
@@ -354,12 +323,13 @@ impl<Other: RemoteStorage> GenericRemoteStorage<Arc<Other>> {
         prefix: Option<&RemotePath>,
         mode: ListingMode,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<Listing, DownloadError> {
         match self {
-            Self::LocalFs(s) => s.list(prefix, mode, max_keys).await,
-            Self::AwsS3(s) => s.list(prefix, mode, max_keys).await,
-            Self::AzureBlob(s) => s.list(prefix, mode, max_keys).await,
-            Self::Unreliable(s) => s.list(prefix, mode, max_keys).await,
+            Self::LocalFs(s) => s.list(prefix, mode, max_keys, cancel).await,
+            Self::AwsS3(s) => s.list(prefix, mode, max_keys, cancel).await,
+            Self::AzureBlob(s) => s.list(prefix, mode, max_keys, cancel).await,
+            Self::Unreliable(s) => s.list(prefix, mode, max_keys, cancel).await,
         }
     }
 
@@ -372,12 +342,13 @@ impl<Other: RemoteStorage> GenericRemoteStorage<Arc<Other>> {
         &self,
         folder: Option<&RemotePath>,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> Result<Vec<RemotePath>, DownloadError> {
         match self {
-            Self::LocalFs(s) => s.list_files(folder, max_keys).await,
-            Self::AwsS3(s) => s.list_files(folder, max_keys).await,
-            Self::AzureBlob(s) => s.list_files(folder, max_keys).await,
-            Self::Unreliable(s) => s.list_files(folder, max_keys).await,
+            Self::LocalFs(s) => s.list_files(folder, max_keys, cancel).await,
+            Self::AwsS3(s) => s.list_files(folder, max_keys, cancel).await,
+            Self::AzureBlob(s) => s.list_files(folder, max_keys, cancel).await,
+            Self::Unreliable(s) => s.list_files(folder, max_keys, cancel).await,
         }
     }
 
@@ -387,36 +358,43 @@ impl<Other: RemoteStorage> GenericRemoteStorage<Arc<Other>> {
     pub async fn list_prefixes(
         &self,
         prefix: Option<&RemotePath>,
+        cancel: &CancellationToken,
     ) -> Result<Vec<RemotePath>, DownloadError> {
         match self {
-            Self::LocalFs(s) => s.list_prefixes(prefix).await,
-            Self::AwsS3(s) => s.list_prefixes(prefix).await,
-            Self::AzureBlob(s) => s.list_prefixes(prefix).await,
-            Self::Unreliable(s) => s.list_prefixes(prefix).await,
+            Self::LocalFs(s) => s.list_prefixes(prefix, cancel).await,
+            Self::AwsS3(s) => s.list_prefixes(prefix, cancel).await,
+            Self::AzureBlob(s) => s.list_prefixes(prefix, cancel).await,
+            Self::Unreliable(s) => s.list_prefixes(prefix, cancel).await,
         }
     }
 
+    /// See [`RemoteStorage::upload`]
     pub async fn upload(
         &self,
         from: impl Stream<Item = std::io::Result<Bytes>> + Send + Sync + 'static,
         data_size_bytes: usize,
         to: &RemotePath,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
         match self {
-            Self::LocalFs(s) => s.upload(from, data_size_bytes, to, metadata).await,
-            Self::AwsS3(s) => s.upload(from, data_size_bytes, to, metadata).await,
-            Self::AzureBlob(s) => s.upload(from, data_size_bytes, to, metadata).await,
-            Self::Unreliable(s) => s.upload(from, data_size_bytes, to, metadata).await,
+            Self::LocalFs(s) => s.upload(from, data_size_bytes, to, metadata, cancel).await,
+            Self::AwsS3(s) => s.upload(from, data_size_bytes, to, metadata, cancel).await,
+            Self::AzureBlob(s) => s.upload(from, data_size_bytes, to, metadata, cancel).await,
+            Self::Unreliable(s) => s.upload(from, data_size_bytes, to, metadata, cancel).await,
         }
     }
 
-    pub async fn download(&self, from: &RemotePath) -> Result<Download, DownloadError> {
+    pub async fn download(
+        &self,
+        from: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError> {
         match self {
-            Self::LocalFs(s) => s.download(from).await,
-            Self::AwsS3(s) => s.download(from).await,
-            Self::AzureBlob(s) => s.download(from).await,
-            Self::Unreliable(s) => s.download(from).await,
+            Self::LocalFs(s) => s.download(from, cancel).await,
+            Self::AwsS3(s) => s.download(from, cancel).await,
+            Self::AzureBlob(s) => s.download(from, cancel).await,
+            Self::Unreliable(s) => s.download(from, cancel).await,
         }
     }
 
@@ -425,54 +403,72 @@ impl<Other: RemoteStorage> GenericRemoteStorage<Arc<Other>> {
         from: &RemotePath,
         start_inclusive: u64,
         end_exclusive: Option<u64>,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
         match self {
             Self::LocalFs(s) => {
-                s.download_byte_range(from, start_inclusive, end_exclusive)
+                s.download_byte_range(from, start_inclusive, end_exclusive, cancel)
                     .await
             }
             Self::AwsS3(s) => {
-                s.download_byte_range(from, start_inclusive, end_exclusive)
+                s.download_byte_range(from, start_inclusive, end_exclusive, cancel)
                     .await
             }
             Self::AzureBlob(s) => {
-                s.download_byte_range(from, start_inclusive, end_exclusive)
+                s.download_byte_range(from, start_inclusive, end_exclusive, cancel)
                     .await
             }
             Self::Unreliable(s) => {
-                s.download_byte_range(from, start_inclusive, end_exclusive)
+                s.download_byte_range(from, start_inclusive, end_exclusive, cancel)
                     .await
             }
         }
     }
 
-    pub async fn delete(&self, path: &RemotePath) -> anyhow::Result<()> {
+    /// See [`RemoteStorage::delete`]
+    pub async fn delete(
+        &self,
+        path: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         match self {
-            Self::LocalFs(s) => s.delete(path).await,
-            Self::AwsS3(s) => s.delete(path).await,
-            Self::AzureBlob(s) => s.delete(path).await,
-            Self::Unreliable(s) => s.delete(path).await,
+            Self::LocalFs(s) => s.delete(path, cancel).await,
+            Self::AwsS3(s) => s.delete(path, cancel).await,
+            Self::AzureBlob(s) => s.delete(path, cancel).await,
+            Self::Unreliable(s) => s.delete(path, cancel).await,
         }
     }
 
-    pub async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()> {
+    /// See [`RemoteStorage::delete_objects`]
+    pub async fn delete_objects(
+        &self,
+        paths: &[RemotePath],
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         match self {
-            Self::LocalFs(s) => s.delete_objects(paths).await,
-            Self::AwsS3(s) => s.delete_objects(paths).await,
-            Self::AzureBlob(s) => s.delete_objects(paths).await,
-            Self::Unreliable(s) => s.delete_objects(paths).await,
+            Self::LocalFs(s) => s.delete_objects(paths, cancel).await,
+            Self::AwsS3(s) => s.delete_objects(paths, cancel).await,
+            Self::AzureBlob(s) => s.delete_objects(paths, cancel).await,
+            Self::Unreliable(s) => s.delete_objects(paths, cancel).await,
         }
     }
 
-    pub async fn copy_object(&self, from: &RemotePath, to: &RemotePath) -> anyhow::Result<()> {
+    /// See [`RemoteStorage::copy`]
+    pub async fn copy_object(
+        &self,
+        from: &RemotePath,
+        to: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         match self {
-            Self::LocalFs(s) => s.copy(from, to).await,
-            Self::AwsS3(s) => s.copy(from, to).await,
-            Self::AzureBlob(s) => s.copy(from, to).await,
-            Self::Unreliable(s) => s.copy(from, to).await,
+            Self::LocalFs(s) => s.copy(from, to, cancel).await,
+            Self::AwsS3(s) => s.copy(from, to, cancel).await,
+            Self::AzureBlob(s) => s.copy(from, to, cancel).await,
+            Self::Unreliable(s) => s.copy(from, to, cancel).await,
         }
     }
 
+    /// See [`RemoteStorage::time_travel_recover`].
     pub async fn time_travel_recover(
         &self,
         prefix: Option<&RemotePath>,
@@ -503,10 +499,11 @@ impl<Other: RemoteStorage> GenericRemoteStorage<Arc<Other>> {
 
 impl GenericRemoteStorage {
     pub fn from_config(storage_config: &RemoteStorageConfig) -> anyhow::Result<Self> {
+        let timeout = storage_config.timeout;
         Ok(match &storage_config.storage {
-            RemoteStorageKind::LocalFs(root) => {
-                info!("Using fs root '{root}' as a remote storage");
-                Self::LocalFs(LocalFs::new(root.clone())?)
+            RemoteStorageKind::LocalFs(path) => {
+                info!("Using fs root '{path}' as a remote storage");
+                Self::LocalFs(LocalFs::new(path.clone(), timeout)?)
             }
             RemoteStorageKind::AwsS3(s3_config) => {
                 // The profile and access key id are only printed here for debugging purposes,
@@ -516,12 +513,12 @@ impl GenericRemoteStorage {
                     std::env::var("AWS_ACCESS_KEY_ID").unwrap_or_else(|_| "<none>".into());
                 info!("Using s3 bucket '{}' in region '{}' as a remote storage, prefix in bucket: '{:?}', bucket endpoint: '{:?}', profile: {profile}, access_key_id: {access_key_id}",
                       s3_config.bucket_name, s3_config.bucket_region, s3_config.prefix_in_bucket, s3_config.endpoint);
-                Self::AwsS3(Arc::new(S3Bucket::new(s3_config)?))
+                Self::AwsS3(Arc::new(S3Bucket::new(s3_config, timeout)?))
             }
             RemoteStorageKind::AzureContainer(azure_config) => {
                 info!("Using azure container '{}' in region '{}' as a remote storage, prefix in container: '{:?}'",
                       azure_config.container_name, azure_config.container_region, azure_config.prefix_in_container);
-                Self::AzureBlob(Arc::new(AzureBlobStorage::new(azure_config)?))
+                Self::AzureBlob(Arc::new(AzureBlobStorage::new(azure_config, timeout)?))
             }
         })
     }
@@ -530,18 +527,15 @@ impl GenericRemoteStorage {
         Self::Unreliable(Arc::new(UnreliableWrapper::new(s, fail_first)))
     }
 
-    /// Takes storage object contents and its size and uploads to remote storage,
-    /// mapping `from_path` to the corresponding remote object id in the storage.
-    ///
-    /// The storage object does not have to be present on the `from_path`,
-    /// this path is used for the remote object id conversion only.
+    /// See [`RemoteStorage::upload`], which this method calls with `None` as metadata.
     pub async fn upload_storage_object(
         &self,
         from: impl Stream<Item = std::io::Result<Bytes>> + Send + Sync + 'static,
         from_size_bytes: usize,
         to: &RemotePath,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
-        self.upload(from, from_size_bytes, to, None)
+        self.upload(from, from_size_bytes, to, None, cancel)
             .await
             .with_context(|| {
                 format!("Failed to upload data of length {from_size_bytes} to storage path {to:?}")
@@ -554,10 +548,11 @@ impl GenericRemoteStorage {
         &self,
         byte_range: Option<(u64, Option<u64>)>,
         from: &RemotePath,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
         match byte_range {
-            Some((start, end)) => self.download_byte_range(from, start, end).await,
-            None => self.download(from).await,
+            Some((start, end)) => self.download_byte_range(from, start, end, cancel).await,
+            None => self.download(from, cancel).await,
         }
     }
 }
@@ -572,6 +567,9 @@ pub struct StorageMetadata(HashMap<String, String>);
 pub struct RemoteStorageConfig {
     /// The storage connection configuration.
     pub storage: RemoteStorageKind,
+    /// A common timeout enforced for all requests after concurrency limiter permit has been
+    /// acquired.
+    pub timeout: Duration,
 }
 
 /// A kind of a remote storage to connect to, with its connection configuration.
@@ -656,6 +654,8 @@ impl Debug for AzureConfig {
 }
 
 impl RemoteStorageConfig {
+    pub const DEFAULT_TIMEOUT: Duration = std::time::Duration::from_secs(120);
+
     pub fn from_toml(toml: &toml_edit::Item) -> anyhow::Result<Option<RemoteStorageConfig>> {
         let local_path = toml.get("local_path");
         let bucket_name = toml.get("bucket_name");
@@ -685,6 +685,27 @@ impl RemoteStorageConfig {
             .map(|endpoint| parse_toml_string("endpoint", endpoint))
             .transpose()?;
 
+        let timeout = toml
+            .get("timeout")
+            .map(|timeout| {
+                timeout
+                    .as_str()
+                    .ok_or_else(|| anyhow::Error::msg("timeout was not a string"))
+            })
+            .transpose()
+            .and_then(|timeout| {
+                timeout
+                    .map(humantime::parse_duration)
+                    .transpose()
+                    .map_err(anyhow::Error::new)
+            })
+            .context("parse timeout")?
+            .unwrap_or(Self::DEFAULT_TIMEOUT);
+
+        if timeout < Duration::from_secs(1) {
+            bail!("timeout was specified as {timeout:?} which is too low");
+        }
+
         let storage = match (
             local_path,
             bucket_name,
@@ -746,7 +767,7 @@ impl RemoteStorageConfig {
             }
         };
 
-        Ok(Some(RemoteStorageConfig { storage }))
+        Ok(Some(RemoteStorageConfig { storage, timeout }))
     }
 }
 
@@ -842,4 +863,24 @@ mod tests {
         let err = RemotePath::new(Utf8Path::new("/")).expect_err("Should fail on absolute paths");
         assert_eq!(err.to_string(), "Path \"/\" is not relative");
     }
+
+    #[test]
+    fn parse_localfs_config_with_timeout() {
+        let input = "local_path = '.'
+timeout = '5s'";
+
+        let toml = input.parse::<toml_edit::Document>().unwrap();
+
+        let config = RemoteStorageConfig::from_toml(toml.as_item())
+            .unwrap()
+            .expect("it exists");
+
+        assert_eq!(
+            config,
+            RemoteStorageConfig {
+                storage: RemoteStorageKind::LocalFs(Utf8PathBuf::from(".")),
+                timeout: Duration::from_secs(5)
+            }
+        );
+    }
 }
diff --git a/libs/remote_storage/src/local_fs.rs b/libs/remote_storage/src/local_fs.rs
index e88111e8e2..6f847cf9d7 100644
--- a/libs/remote_storage/src/local_fs.rs
+++ b/libs/remote_storage/src/local_fs.rs
@@ -5,7 +5,12 @@
 //! volume is mounted to the local FS.
 
 use std::{
-    borrow::Cow, future::Future, io::ErrorKind, num::NonZeroU32, pin::Pin, time::SystemTime,
+    borrow::Cow,
+    future::Future,
+    io::ErrorKind,
+    num::NonZeroU32,
+    pin::Pin,
+    time::{Duration, SystemTime},
 };
 
 use anyhow::{bail, ensure, Context};
@@ -20,7 +25,9 @@ use tokio_util::{io::ReaderStream, sync::CancellationToken};
 use tracing::*;
 use utils::{crashsafe::path_with_suffix_extension, fs_ext::is_directory_empty};
 
-use crate::{Download, DownloadError, Listing, ListingMode, RemotePath, TimeTravelError};
+use crate::{
+    Download, DownloadError, Listing, ListingMode, RemotePath, TimeTravelError, TimeoutOrCancel,
+};
 
 use super::{RemoteStorage, StorageMetadata};
 
@@ -29,12 +36,13 @@ const LOCAL_FS_TEMP_FILE_SUFFIX: &str = "___temp";
 #[derive(Debug, Clone)]
 pub struct LocalFs {
     storage_root: Utf8PathBuf,
+    timeout: Duration,
 }
 
 impl LocalFs {
     /// Attempts to create local FS storage, along with its root directory.
     /// Storage root will be created (if does not exist) and transformed into an absolute path (if passed as relative).
-    pub fn new(mut storage_root: Utf8PathBuf) -> anyhow::Result<Self> {
+    pub fn new(mut storage_root: Utf8PathBuf, timeout: Duration) -> anyhow::Result<Self> {
         if !storage_root.exists() {
             std::fs::create_dir_all(&storage_root).with_context(|| {
                 format!("Failed to create all directories in the given root path {storage_root:?}")
@@ -46,7 +54,10 @@ impl LocalFs {
             })?;
         }
 
-        Ok(Self { storage_root })
+        Ok(Self {
+            storage_root,
+            timeout,
+        })
     }
 
     // mirrors S3Bucket::s3_object_to_relative_path
@@ -157,80 +168,14 @@ impl LocalFs {
 
         Ok(files)
     }
-}
 
-impl RemoteStorage for LocalFs {
-    async fn list(
-        &self,
-        prefix: Option<&RemotePath>,
-        mode: ListingMode,
-        max_keys: Option<NonZeroU32>,
-    ) -> Result<Listing, DownloadError> {
-        let mut result = Listing::default();
-
-        if let ListingMode::NoDelimiter = mode {
-            let keys = self
-                .list_recursive(prefix)
-                .await
-                .map_err(DownloadError::Other)?;
-
-            result.keys = keys
-                .into_iter()
-                .filter(|k| {
-                    let path = k.with_base(&self.storage_root);
-                    !path.is_dir()
-                })
-                .collect();
-            if let Some(max_keys) = max_keys {
-                result.keys.truncate(max_keys.get() as usize);
-            }
-
-            return Ok(result);
-        }
-
-        let path = match prefix {
-            Some(prefix) => Cow::Owned(prefix.with_base(&self.storage_root)),
-            None => Cow::Borrowed(&self.storage_root),
-        };
-
-        let prefixes_to_filter = get_all_files(path.as_ref(), false)
-            .await
-            .map_err(DownloadError::Other)?;
-
-        // filter out empty directories to mirror s3 behavior.
-        for prefix in prefixes_to_filter {
-            if prefix.is_dir()
-                && is_directory_empty(&prefix)
-                    .await
-                    .map_err(DownloadError::Other)?
-            {
-                continue;
-            }
-
-            let stripped = prefix
-                .strip_prefix(&self.storage_root)
-                .context("Failed to strip prefix")
-                .and_then(RemotePath::new)
-                .expect(
-                    "We list files for storage root, hence should be able to remote the prefix",
-                );
-
-            if prefix.is_dir() {
-                result.prefixes.push(stripped);
-            } else {
-                result.keys.push(stripped);
-            }
-        }
-
-        Ok(result)
-    }
-
-    async fn upload(
+    async fn upload0(
         &self,
         data: impl Stream<Item = std::io::Result<Bytes>> + Send + Sync,
         data_size_bytes: usize,
         to: &RemotePath,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
         let target_file_path = to.with_base(&self.storage_root);
         create_target_directory(&target_file_path).await?;
@@ -265,9 +210,26 @@ impl RemoteStorage for LocalFs {
         let mut buffer_to_read = data.take(from_size_bytes);
 
         // alternatively we could just write the bytes to a file, but local_fs is a testing utility
-        let bytes_read = io::copy_buf(&mut buffer_to_read, &mut destination)
-            .await
-            .with_context(|| {
+        let copy = io::copy_buf(&mut buffer_to_read, &mut destination);
+
+        let bytes_read = tokio::select! {
+            biased;
+            _ = cancel.cancelled() => {
+                let file = destination.into_inner();
+                // wait for the inflight operation(s) to complete so that there could be a next
+                // attempt right away and our writes are not directed to their file.
+                file.into_std().await;
+
+                // TODO: leave the temp or not? leaving is probably less racy. enabled truncate at
+                // least.
+                fs::remove_file(temp_file_path).await.context("remove temp_file_path after cancellation or timeout")?;
+                return Err(TimeoutOrCancel::Cancel.into());
+            }
+            read = copy => read,
+        };
+
+        let bytes_read =
+            bytes_read.with_context(|| {
                 format!(
                     "Failed to upload file (write temp) to the local storage at '{temp_file_path}'",
                 )
@@ -299,6 +261,9 @@ impl RemoteStorage for LocalFs {
             })?;
 
         if let Some(storage_metadata) = metadata {
+            // FIXME: we must not be using metadata much, since this would forget the old metadata
+            // for new writes? or perhaps metadata is sticky; could consider removing if it's never
+            // used.
             let storage_metadata_path = storage_metadata_path(&target_file_path);
             fs::write(
                 &storage_metadata_path,
@@ -315,8 +280,131 @@ impl RemoteStorage for LocalFs {
 
         Ok(())
     }
+}
 
-    async fn download(&self, from: &RemotePath) -> Result<Download, DownloadError> {
+impl RemoteStorage for LocalFs {
+    async fn list(
+        &self,
+        prefix: Option<&RemotePath>,
+        mode: ListingMode,
+        max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
+    ) -> Result<Listing, DownloadError> {
+        let op = async {
+            let mut result = Listing::default();
+
+            if let ListingMode::NoDelimiter = mode {
+                let keys = self
+                    .list_recursive(prefix)
+                    .await
+                    .map_err(DownloadError::Other)?;
+
+                result.keys = keys
+                    .into_iter()
+                    .filter(|k| {
+                        let path = k.with_base(&self.storage_root);
+                        !path.is_dir()
+                    })
+                    .collect();
+
+                if let Some(max_keys) = max_keys {
+                    result.keys.truncate(max_keys.get() as usize);
+                }
+
+                return Ok(result);
+            }
+
+            let path = match prefix {
+                Some(prefix) => Cow::Owned(prefix.with_base(&self.storage_root)),
+                None => Cow::Borrowed(&self.storage_root),
+            };
+
+            let prefixes_to_filter = get_all_files(path.as_ref(), false)
+                .await
+                .map_err(DownloadError::Other)?;
+
+            // filter out empty directories to mirror s3 behavior.
+            for prefix in prefixes_to_filter {
+                if prefix.is_dir()
+                    && is_directory_empty(&prefix)
+                        .await
+                        .map_err(DownloadError::Other)?
+                {
+                    continue;
+                }
+
+                let stripped = prefix
+                    .strip_prefix(&self.storage_root)
+                    .context("Failed to strip prefix")
+                    .and_then(RemotePath::new)
+                    .expect(
+                        "We list files for storage root, hence should be able to remote the prefix",
+                    );
+
+                if prefix.is_dir() {
+                    result.prefixes.push(stripped);
+                } else {
+                    result.keys.push(stripped);
+                }
+            }
+
+            Ok(result)
+        };
+
+        let timeout = async {
+            tokio::time::sleep(self.timeout).await;
+            Err(DownloadError::Timeout)
+        };
+
+        let cancelled = async {
+            cancel.cancelled().await;
+            Err(DownloadError::Cancelled)
+        };
+
+        tokio::select! {
+            res = op => res,
+            res = timeout => res,
+            res = cancelled => res,
+        }
+    }
+
+    async fn upload(
+        &self,
+        data: impl Stream<Item = std::io::Result<Bytes>> + Send + Sync,
+        data_size_bytes: usize,
+        to: &RemotePath,
+        metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
+        let cancel = cancel.child_token();
+
+        let op = self.upload0(data, data_size_bytes, to, metadata, &cancel);
+        let mut op = std::pin::pin!(op);
+
+        // race the upload0 to the timeout; if it goes over, do a graceful shutdown
+        let (res, timeout) = tokio::select! {
+            res = &mut op => (res, false),
+            _ = tokio::time::sleep(self.timeout) => {
+                cancel.cancel();
+                (op.await, true)
+            }
+        };
+
+        match res {
+            Err(e) if timeout && TimeoutOrCancel::caused_by_cancel(&e) => {
+                // we caused this cancel (or they happened simultaneously) -- swap it out to
+                // Timeout
+                Err(TimeoutOrCancel::Timeout.into())
+            }
+            res => res,
+        }
+    }
+
+    async fn download(
+        &self,
+        from: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError> {
         let target_path = from.with_base(&self.storage_root);
         if file_exists(&target_path).map_err(DownloadError::BadInput)? {
             let source = ReaderStream::new(
@@ -334,6 +422,10 @@ impl RemoteStorage for LocalFs {
                 .read_storage_metadata(&target_path)
                 .await
                 .map_err(DownloadError::Other)?;
+
+            let cancel_or_timeout = crate::support::cancel_or_timeout(self.timeout, cancel.clone());
+            let source = crate::support::DownloadStream::new(cancel_or_timeout, source);
+
             Ok(Download {
                 metadata,
                 last_modified: None,
@@ -350,6 +442,7 @@ impl RemoteStorage for LocalFs {
         from: &RemotePath,
         start_inclusive: u64,
         end_exclusive: Option<u64>,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
         if let Some(end_exclusive) = end_exclusive {
             if end_exclusive <= start_inclusive {
@@ -391,6 +484,9 @@ impl RemoteStorage for LocalFs {
             let source = source.take(end_exclusive.unwrap_or(len) - start_inclusive);
             let source = ReaderStream::new(source);
 
+            let cancel_or_timeout = crate::support::cancel_or_timeout(self.timeout, cancel.clone());
+            let source = crate::support::DownloadStream::new(cancel_or_timeout, source);
+
             Ok(Download {
                 metadata,
                 last_modified: None,
@@ -402,7 +498,7 @@ impl RemoteStorage for LocalFs {
         }
     }
 
-    async fn delete(&self, path: &RemotePath) -> anyhow::Result<()> {
+    async fn delete(&self, path: &RemotePath, _cancel: &CancellationToken) -> anyhow::Result<()> {
         let file_path = path.with_base(&self.storage_root);
         match fs::remove_file(&file_path).await {
             Ok(()) => Ok(()),
@@ -414,14 +510,23 @@ impl RemoteStorage for LocalFs {
         }
     }
 
-    async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()> {
+    async fn delete_objects<'a>(
+        &self,
+        paths: &'a [RemotePath],
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         for path in paths {
-            self.delete(path).await?
+            self.delete(path, cancel).await?
         }
         Ok(())
     }
 
-    async fn copy(&self, from: &RemotePath, to: &RemotePath) -> anyhow::Result<()> {
+    async fn copy(
+        &self,
+        from: &RemotePath,
+        to: &RemotePath,
+        _cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         let from_path = from.with_base(&self.storage_root);
         let to_path = to.with_base(&self.storage_root);
         create_target_directory(&to_path).await?;
@@ -528,8 +633,9 @@ mod fs_tests {
         remote_storage_path: &RemotePath,
         expected_metadata: Option<&StorageMetadata>,
     ) -> anyhow::Result<String> {
+        let cancel = CancellationToken::new();
         let download = storage
-            .download(remote_storage_path)
+            .download(remote_storage_path, &cancel)
             .await
             .map_err(|e| anyhow::anyhow!("Download failed: {e}"))?;
         ensure!(
@@ -544,16 +650,16 @@ mod fs_tests {
 
     #[tokio::test]
     async fn upload_file() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
 
-        let target_path_1 = upload_dummy_file(&storage, "upload_1", None).await?;
+        let target_path_1 = upload_dummy_file(&storage, "upload_1", None, &cancel).await?;
         assert_eq!(
             storage.list_all().await?,
             vec![target_path_1.clone()],
             "Should list a single file after first upload"
         );
 
-        let target_path_2 = upload_dummy_file(&storage, "upload_2", None).await?;
+        let target_path_2 = upload_dummy_file(&storage, "upload_2", None, &cancel).await?;
         assert_eq!(
             list_files_sorted(&storage).await?,
             vec![target_path_1.clone(), target_path_2.clone()],
@@ -565,7 +671,7 @@ mod fs_tests {
 
     #[tokio::test]
     async fn upload_file_negatives() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
 
         let id = RemotePath::new(Utf8Path::new("dummy"))?;
         let content = Bytes::from_static(b"12345");
@@ -574,34 +680,34 @@ mod fs_tests {
         // Check that you get an error if the size parameter doesn't match the actual
         // size of the stream.
         storage
-            .upload(content(), 0, &id, None)
+            .upload(content(), 0, &id, None, &cancel)
             .await
             .expect_err("upload with zero size succeeded");
         storage
-            .upload(content(), 4, &id, None)
+            .upload(content(), 4, &id, None, &cancel)
             .await
             .expect_err("upload with too short size succeeded");
         storage
-            .upload(content(), 6, &id, None)
+            .upload(content(), 6, &id, None, &cancel)
             .await
             .expect_err("upload with too large size succeeded");
 
         // Correct size is 5, this should succeed.
-        storage.upload(content(), 5, &id, None).await?;
+        storage.upload(content(), 5, &id, None, &cancel).await?;
 
         Ok(())
     }
 
-    fn create_storage() -> anyhow::Result<LocalFs> {
+    fn create_storage() -> anyhow::Result<(LocalFs, CancellationToken)> {
         let storage_root = tempdir()?.path().to_path_buf();
-        LocalFs::new(storage_root)
+        LocalFs::new(storage_root, Duration::from_secs(120)).map(|s| (s, CancellationToken::new()))
     }
 
     #[tokio::test]
     async fn download_file() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
         let upload_name = "upload_1";
-        let upload_target = upload_dummy_file(&storage, upload_name, None).await?;
+        let upload_target = upload_dummy_file(&storage, upload_name, None, &cancel).await?;
 
         let contents = read_and_check_metadata(&storage, &upload_target, None).await?;
         assert_eq!(
@@ -611,7 +717,7 @@ mod fs_tests {
         );
 
         let non_existing_path = "somewhere/else";
-        match storage.download(&RemotePath::new(Utf8Path::new(non_existing_path))?).await {
+        match storage.download(&RemotePath::new(Utf8Path::new(non_existing_path))?, &cancel).await {
             Err(DownloadError::NotFound) => {} // Should get NotFound for non existing keys
             other => panic!("Should get a NotFound error when downloading non-existing storage files, but got: {other:?}"),
         }
@@ -620,9 +726,9 @@ mod fs_tests {
 
     #[tokio::test]
     async fn download_file_range_positive() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
         let upload_name = "upload_1";
-        let upload_target = upload_dummy_file(&storage, upload_name, None).await?;
+        let upload_target = upload_dummy_file(&storage, upload_name, None, &cancel).await?;
 
         let full_range_download_contents =
             read_and_check_metadata(&storage, &upload_target, None).await?;
@@ -636,7 +742,12 @@ mod fs_tests {
         let (first_part_local, second_part_local) = uploaded_bytes.split_at(3);
 
         let first_part_download = storage
-            .download_byte_range(&upload_target, 0, Some(first_part_local.len() as u64))
+            .download_byte_range(
+                &upload_target,
+                0,
+                Some(first_part_local.len() as u64),
+                &cancel,
+            )
             .await?;
         assert!(
             first_part_download.metadata.is_none(),
@@ -654,6 +765,7 @@ mod fs_tests {
                 &upload_target,
                 first_part_local.len() as u64,
                 Some((first_part_local.len() + second_part_local.len()) as u64),
+                &cancel,
             )
             .await?;
         assert!(
@@ -668,7 +780,7 @@ mod fs_tests {
         );
 
         let suffix_bytes = storage
-            .download_byte_range(&upload_target, 13, None)
+            .download_byte_range(&upload_target, 13, None, &cancel)
             .await?
             .download_stream;
         let suffix_bytes = aggregate(suffix_bytes).await?;
@@ -676,7 +788,7 @@ mod fs_tests {
         assert_eq!(upload_name, suffix);
 
         let all_bytes = storage
-            .download_byte_range(&upload_target, 0, None)
+            .download_byte_range(&upload_target, 0, None, &cancel)
             .await?
             .download_stream;
         let all_bytes = aggregate(all_bytes).await?;
@@ -688,9 +800,9 @@ mod fs_tests {
 
     #[tokio::test]
     async fn download_file_range_negative() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
         let upload_name = "upload_1";
-        let upload_target = upload_dummy_file(&storage, upload_name, None).await?;
+        let upload_target = upload_dummy_file(&storage, upload_name, None, &cancel).await?;
 
         let start = 1_000_000_000;
         let end = start + 1;
@@ -699,6 +811,7 @@ mod fs_tests {
                 &upload_target,
                 start,
                 Some(end), // exclusive end
+                &cancel,
             )
             .await
         {
@@ -715,7 +828,7 @@ mod fs_tests {
         let end = 234;
         assert!(start > end, "Should test an incorrect range");
         match storage
-            .download_byte_range(&upload_target, start, Some(end))
+            .download_byte_range(&upload_target, start, Some(end), &cancel)
             .await
         {
             Ok(_) => panic!("Should not allow downloading wrong ranges"),
@@ -732,15 +845,15 @@ mod fs_tests {
 
     #[tokio::test]
     async fn delete_file() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
         let upload_name = "upload_1";
-        let upload_target = upload_dummy_file(&storage, upload_name, None).await?;
+        let upload_target = upload_dummy_file(&storage, upload_name, None, &cancel).await?;
 
-        storage.delete(&upload_target).await?;
+        storage.delete(&upload_target, &cancel).await?;
         assert!(storage.list_all().await?.is_empty());
 
         storage
-            .delete(&upload_target)
+            .delete(&upload_target, &cancel)
             .await
             .expect("Should allow deleting non-existing storage files");
 
@@ -749,14 +862,14 @@ mod fs_tests {
 
     #[tokio::test]
     async fn file_with_metadata() -> anyhow::Result<()> {
-        let storage = create_storage()?;
+        let (storage, cancel) = create_storage()?;
         let upload_name = "upload_1";
         let metadata = StorageMetadata(HashMap::from([
             ("one".to_string(), "1".to_string()),
             ("two".to_string(), "2".to_string()),
         ]));
         let upload_target =
-            upload_dummy_file(&storage, upload_name, Some(metadata.clone())).await?;
+            upload_dummy_file(&storage, upload_name, Some(metadata.clone()), &cancel).await?;
 
         let full_range_download_contents =
             read_and_check_metadata(&storage, &upload_target, Some(&metadata)).await?;
@@ -770,7 +883,12 @@ mod fs_tests {
         let (first_part_local, _) = uploaded_bytes.split_at(3);
 
         let partial_download_with_metadata = storage
-            .download_byte_range(&upload_target, 0, Some(first_part_local.len() as u64))
+            .download_byte_range(
+                &upload_target,
+                0,
+                Some(first_part_local.len() as u64),
+                &cancel,
+            )
             .await?;
         let first_part_remote = aggregate(partial_download_with_metadata.download_stream).await?;
         assert_eq!(
@@ -791,16 +909,20 @@ mod fs_tests {
     #[tokio::test]
     async fn list() -> anyhow::Result<()> {
         // No delimiter: should recursively list everything
-        let storage = create_storage()?;
-        let child = upload_dummy_file(&storage, "grandparent/parent/child", None).await?;
-        let uncle = upload_dummy_file(&storage, "grandparent/uncle", None).await?;
+        let (storage, cancel) = create_storage()?;
+        let child = upload_dummy_file(&storage, "grandparent/parent/child", None, &cancel).await?;
+        let uncle = upload_dummy_file(&storage, "grandparent/uncle", None, &cancel).await?;
 
-        let listing = storage.list(None, ListingMode::NoDelimiter, None).await?;
+        let listing = storage
+            .list(None, ListingMode::NoDelimiter, None, &cancel)
+            .await?;
         assert!(listing.prefixes.is_empty());
         assert_eq!(listing.keys, [uncle.clone(), child.clone()].to_vec());
 
         // Delimiter: should only go one deep
-        let listing = storage.list(None, ListingMode::WithDelimiter, None).await?;
+        let listing = storage
+            .list(None, ListingMode::WithDelimiter, None, &cancel)
+            .await?;
 
         assert_eq!(
             listing.prefixes,
@@ -814,6 +936,7 @@ mod fs_tests {
                 Some(&RemotePath::from_string("timelines/some_timeline/grandparent").unwrap()),
                 ListingMode::WithDelimiter,
                 None,
+                &cancel,
             )
             .await?;
         assert_eq!(
@@ -826,10 +949,75 @@ mod fs_tests {
         Ok(())
     }
 
+    #[tokio::test]
+    async fn overwrite_shorter_file() -> anyhow::Result<()> {
+        let (storage, cancel) = create_storage()?;
+
+        let path = RemotePath::new("does/not/matter/file".into())?;
+
+        let body = Bytes::from_static(b"long file contents is long");
+        {
+            let len = body.len();
+            let body =
+                futures::stream::once(futures::future::ready(std::io::Result::Ok(body.clone())));
+            storage.upload(body, len, &path, None, &cancel).await?;
+        }
+
+        let read = aggregate(storage.download(&path, &cancel).await?.download_stream).await?;
+        assert_eq!(body, read);
+
+        let shorter = Bytes::from_static(b"shorter body");
+        {
+            let len = shorter.len();
+            let body =
+                futures::stream::once(futures::future::ready(std::io::Result::Ok(shorter.clone())));
+            storage.upload(body, len, &path, None, &cancel).await?;
+        }
+
+        let read = aggregate(storage.download(&path, &cancel).await?.download_stream).await?;
+        assert_eq!(shorter, read);
+        Ok(())
+    }
+
+    #[tokio::test]
+    async fn cancelled_upload_can_later_be_retried() -> anyhow::Result<()> {
+        let (storage, cancel) = create_storage()?;
+
+        let path = RemotePath::new("does/not/matter/file".into())?;
+
+        let body = Bytes::from_static(b"long file contents is long");
+        {
+            let len = body.len();
+            let body =
+                futures::stream::once(futures::future::ready(std::io::Result::Ok(body.clone())));
+            let cancel = cancel.child_token();
+            cancel.cancel();
+            let e = storage
+                .upload(body, len, &path, None, &cancel)
+                .await
+                .unwrap_err();
+
+            assert!(TimeoutOrCancel::caused_by_cancel(&e));
+        }
+
+        {
+            let len = body.len();
+            let body =
+                futures::stream::once(futures::future::ready(std::io::Result::Ok(body.clone())));
+            storage.upload(body, len, &path, None, &cancel).await?;
+        }
+
+        let read = aggregate(storage.download(&path, &cancel).await?.download_stream).await?;
+        assert_eq!(body, read);
+
+        Ok(())
+    }
+
     async fn upload_dummy_file(
         storage: &LocalFs,
         name: &str,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<RemotePath> {
         let from_path = storage
             .storage_root
@@ -851,7 +1039,9 @@ mod fs_tests {
 
         let file = tokio_util::io::ReaderStream::new(file);
 
-        storage.upload(file, size, &relative_path, metadata).await?;
+        storage
+            .upload(file, size, &relative_path, metadata, cancel)
+            .await?;
         Ok(relative_path)
     }
 
diff --git a/libs/remote_storage/src/s3_bucket.rs b/libs/remote_storage/src/s3_bucket.rs
index dee5750cac..af70dc7ca2 100644
--- a/libs/remote_storage/src/s3_bucket.rs
+++ b/libs/remote_storage/src/s3_bucket.rs
@@ -11,7 +11,7 @@ use std::{
     pin::Pin,
     sync::Arc,
     task::{Context, Poll},
-    time::SystemTime,
+    time::{Duration, SystemTime},
 };
 
 use anyhow::{anyhow, Context as _};
@@ -46,9 +46,9 @@ use utils::backoff;
 
 use super::StorageMetadata;
 use crate::{
-    support::PermitCarrying, ConcurrencyLimiter, Download, DownloadError, Listing, ListingMode,
-    RemotePath, RemoteStorage, S3Config, TimeTravelError, MAX_KEYS_PER_DELETE,
-    REMOTE_STORAGE_PREFIX_SEPARATOR,
+    error::Cancelled, support::PermitCarrying, ConcurrencyLimiter, Download, DownloadError,
+    Listing, ListingMode, RemotePath, RemoteStorage, S3Config, TimeTravelError, TimeoutOrCancel,
+    MAX_KEYS_PER_DELETE, REMOTE_STORAGE_PREFIX_SEPARATOR,
 };
 
 pub(super) mod metrics;
@@ -63,6 +63,8 @@ pub struct S3Bucket {
     prefix_in_bucket: Option<String>,
     max_keys_per_list_response: Option<i32>,
     concurrency_limiter: ConcurrencyLimiter,
+    // Per-request timeout. Accessible for tests.
+    pub timeout: Duration,
 }
 
 struct GetObjectRequest {
@@ -72,7 +74,7 @@ struct GetObjectRequest {
 }
 impl S3Bucket {
     /// Creates the S3 storage, errors if incorrect AWS S3 configuration provided.
-    pub fn new(aws_config: &S3Config) -> anyhow::Result<Self> {
+    pub fn new(aws_config: &S3Config, timeout: Duration) -> anyhow::Result<Self> {
         tracing::debug!(
             "Creating s3 remote storage for S3 bucket {}",
             aws_config.bucket_name
@@ -152,6 +154,7 @@ impl S3Bucket {
             max_keys_per_list_response: aws_config.max_keys_per_list_response,
             prefix_in_bucket,
             concurrency_limiter: ConcurrencyLimiter::new(aws_config.concurrency_limit.get()),
+            timeout,
         })
     }
 
@@ -185,40 +188,55 @@ impl S3Bucket {
         }
     }
 
-    async fn permit(&self, kind: RequestKind) -> tokio::sync::SemaphorePermit<'_> {
+    async fn permit(
+        &self,
+        kind: RequestKind,
+        cancel: &CancellationToken,
+    ) -> Result<tokio::sync::SemaphorePermit<'_>, Cancelled> {
         let started_at = start_counting_cancelled_wait(kind);
-        let permit = self
-            .concurrency_limiter
-            .acquire(kind)
-            .await
-            .expect("semaphore is never closed");
+        let acquire = self.concurrency_limiter.acquire(kind);
+
+        let permit = tokio::select! {
+            permit = acquire => permit.expect("semaphore is never closed"),
+            _ = cancel.cancelled() => return Err(Cancelled),
+        };
 
         let started_at = ScopeGuard::into_inner(started_at);
         metrics::BUCKET_METRICS
             .wait_seconds
             .observe_elapsed(kind, started_at);
 
-        permit
+        Ok(permit)
     }
 
-    async fn owned_permit(&self, kind: RequestKind) -> tokio::sync::OwnedSemaphorePermit {
+    async fn owned_permit(
+        &self,
+        kind: RequestKind,
+        cancel: &CancellationToken,
+    ) -> Result<tokio::sync::OwnedSemaphorePermit, Cancelled> {
         let started_at = start_counting_cancelled_wait(kind);
-        let permit = self
-            .concurrency_limiter
-            .acquire_owned(kind)
-            .await
-            .expect("semaphore is never closed");
+        let acquire = self.concurrency_limiter.acquire_owned(kind);
+
+        let permit = tokio::select! {
+            permit = acquire => permit.expect("semaphore is never closed"),
+            _ = cancel.cancelled() => return Err(Cancelled),
+        };
 
         let started_at = ScopeGuard::into_inner(started_at);
         metrics::BUCKET_METRICS
             .wait_seconds
             .observe_elapsed(kind, started_at);
-        permit
+        Ok(permit)
     }
 
-    async fn download_object(&self, request: GetObjectRequest) -> Result<Download, DownloadError> {
+    async fn download_object(
+        &self,
+        request: GetObjectRequest,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError> {
         let kind = RequestKind::Get;
-        let permit = self.owned_permit(kind).await;
+
+        let permit = self.owned_permit(kind, cancel).await?;
 
         let started_at = start_measuring_requests(kind);
 
@@ -228,8 +246,13 @@ impl S3Bucket {
             .bucket(request.bucket)
             .key(request.key)
             .set_range(request.range)
-            .send()
-            .await;
+            .send();
+
+        let get_object = tokio::select! {
+            res = get_object => res,
+            _ = tokio::time::sleep(self.timeout) => return Err(DownloadError::Timeout),
+            _ = cancel.cancelled() => return Err(DownloadError::Cancelled),
+        };
 
         let started_at = ScopeGuard::into_inner(started_at);
 
@@ -259,6 +282,10 @@ impl S3Bucket {
             }
         };
 
+        // even if we would have no timeout left, continue anyways. the caller can decide to ignore
+        // the errors considering timeouts and cancellation.
+        let remaining = self.timeout.saturating_sub(started_at.elapsed());
+
         let metadata = object_output.metadata().cloned().map(StorageMetadata);
         let etag = object_output.e_tag;
         let last_modified = object_output.last_modified.and_then(|t| t.try_into().ok());
@@ -268,6 +295,9 @@ impl S3Bucket {
         let body = PermitCarrying::new(permit, body);
         let body = TimedDownload::new(started_at, body);
 
+        let cancel_or_timeout = crate::support::cancel_or_timeout(remaining, cancel.clone());
+        let body = crate::support::DownloadStream::new(cancel_or_timeout, body);
+
         Ok(Download {
             metadata,
             etag,
@@ -278,33 +308,44 @@ impl S3Bucket {
 
     async fn delete_oids(
         &self,
-        kind: RequestKind,
+        _permit: &tokio::sync::SemaphorePermit<'_>,
         delete_objects: &[ObjectIdentifier],
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
+        let kind = RequestKind::Delete;
+        let mut cancel = std::pin::pin!(cancel.cancelled());
+
         for chunk in delete_objects.chunks(MAX_KEYS_PER_DELETE) {
             let started_at = start_measuring_requests(kind);
 
-            let resp = self
+            let req = self
                 .client
                 .delete_objects()
                 .bucket(self.bucket_name.clone())
                 .delete(
                     Delete::builder()
                         .set_objects(Some(chunk.to_vec()))
-                        .build()?,
+                        .build()
+                        .context("build request")?,
                 )
-                .send()
-                .await;
+                .send();
+
+            let resp = tokio::select! {
+                resp = req => resp,
+                _ = tokio::time::sleep(self.timeout) => return Err(TimeoutOrCancel::Timeout.into()),
+                _ = &mut cancel => return Err(TimeoutOrCancel::Cancel.into()),
+            };
 
             let started_at = ScopeGuard::into_inner(started_at);
             metrics::BUCKET_METRICS
                 .req_seconds
                 .observe_elapsed(kind, &resp, started_at);
 
-            let resp = resp?;
+            let resp = resp.context("request deletion")?;
             metrics::BUCKET_METRICS
                 .deleted_objects_total
                 .inc_by(chunk.len() as u64);
+
             if let Some(errors) = resp.errors {
                 // Log a bounded number of the errors within the response:
                 // these requests can carry 1000 keys so logging each one
@@ -320,9 +361,10 @@ impl S3Bucket {
                     );
                 }
 
-                return Err(anyhow::format_err!(
-                    "Failed to delete {} objects",
-                    errors.len()
+                return Err(anyhow::anyhow!(
+                    "Failed to delete {}/{} objects",
+                    errors.len(),
+                    chunk.len(),
                 ));
             }
         }
@@ -410,6 +452,7 @@ impl RemoteStorage for S3Bucket {
         prefix: Option<&RemotePath>,
         mode: ListingMode,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> Result<Listing, DownloadError> {
         let kind = RequestKind::List;
         // s3 sdk wants i32
@@ -431,10 +474,11 @@ impl RemoteStorage for S3Bucket {
                 p
             });
 
+        let _permit = self.permit(kind, cancel).await?;
+
         let mut continuation_token = None;
 
         loop {
-            let _guard = self.permit(kind).await;
             let started_at = start_measuring_requests(kind);
 
             // min of two Options, returning Some if one is value and another is
@@ -456,9 +500,15 @@ impl RemoteStorage for S3Bucket {
                 request = request.delimiter(REMOTE_STORAGE_PREFIX_SEPARATOR.to_string());
             }
 
-            let response = request
-                .send()
-                .await
+            let request = request.send();
+
+            let response = tokio::select! {
+                res = request => res,
+                _ = tokio::time::sleep(self.timeout) => return Err(DownloadError::Timeout),
+                _ = cancel.cancelled() => return Err(DownloadError::Cancelled),
+            };
+
+            let response = response
                 .context("Failed to list S3 prefixes")
                 .map_err(DownloadError::Other);
 
@@ -511,16 +561,17 @@ impl RemoteStorage for S3Bucket {
         from_size_bytes: usize,
         to: &RemotePath,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
         let kind = RequestKind::Put;
-        let _guard = self.permit(kind).await;
+        let _permit = self.permit(kind, cancel).await?;
 
         let started_at = start_measuring_requests(kind);
 
         let body = Body::wrap_stream(from);
         let bytes_stream = ByteStream::new(SdkBody::from_body_0_4(body));
 
-        let res = self
+        let upload = self
             .client
             .put_object()
             .bucket(self.bucket_name.clone())
@@ -528,22 +579,40 @@ impl RemoteStorage for S3Bucket {
             .set_metadata(metadata.map(|m| m.0))
             .content_length(from_size_bytes.try_into()?)
             .body(bytes_stream)
-            .send()
-            .await;
+            .send();
 
-        let started_at = ScopeGuard::into_inner(started_at);
-        metrics::BUCKET_METRICS
-            .req_seconds
-            .observe_elapsed(kind, &res, started_at);
+        let upload = tokio::time::timeout(self.timeout, upload);
 
-        res?;
+        let res = tokio::select! {
+            res = upload => res,
+            _ = cancel.cancelled() => return Err(TimeoutOrCancel::Cancel.into()),
+        };
 
-        Ok(())
+        if let Ok(inner) = &res {
+            // do not incl. timeouts as errors in metrics but cancellations
+            let started_at = ScopeGuard::into_inner(started_at);
+            metrics::BUCKET_METRICS
+                .req_seconds
+                .observe_elapsed(kind, inner, started_at);
+        }
+
+        match res {
+            Ok(Ok(_put)) => Ok(()),
+            Ok(Err(sdk)) => Err(sdk.into()),
+            Err(_timeout) => Err(TimeoutOrCancel::Timeout.into()),
+        }
     }
 
-    async fn copy(&self, from: &RemotePath, to: &RemotePath) -> anyhow::Result<()> {
+    async fn copy(
+        &self,
+        from: &RemotePath,
+        to: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         let kind = RequestKind::Copy;
-        let _guard = self.permit(kind).await;
+        let _permit = self.permit(kind, cancel).await?;
+
+        let timeout = tokio::time::sleep(self.timeout);
 
         let started_at = start_measuring_requests(kind);
 
@@ -554,14 +623,19 @@ impl RemoteStorage for S3Bucket {
             self.relative_path_to_s3_object(from)
         );
 
-        let res = self
+        let op = self
             .client
             .copy_object()
             .bucket(self.bucket_name.clone())
             .key(self.relative_path_to_s3_object(to))
             .copy_source(copy_source)
-            .send()
-            .await;
+            .send();
+
+        let res = tokio::select! {
+            res = op => res,
+            _ = timeout => return Err(TimeoutOrCancel::Timeout.into()),
+            _ = cancel.cancelled() => return Err(TimeoutOrCancel::Cancel.into()),
+        };
 
         let started_at = ScopeGuard::into_inner(started_at);
         metrics::BUCKET_METRICS
@@ -573,14 +647,21 @@ impl RemoteStorage for S3Bucket {
         Ok(())
     }
 
-    async fn download(&self, from: &RemotePath) -> Result<Download, DownloadError> {
+    async fn download(
+        &self,
+        from: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError> {
         // if prefix is not none then download file `prefix/from`
         // if prefix is none then download file `from`
-        self.download_object(GetObjectRequest {
-            bucket: self.bucket_name.clone(),
-            key: self.relative_path_to_s3_object(from),
-            range: None,
-        })
+        self.download_object(
+            GetObjectRequest {
+                bucket: self.bucket_name.clone(),
+                key: self.relative_path_to_s3_object(from),
+                range: None,
+            },
+            cancel,
+        )
         .await
     }
 
@@ -589,6 +670,7 @@ impl RemoteStorage for S3Bucket {
         from: &RemotePath,
         start_inclusive: u64,
         end_exclusive: Option<u64>,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
         // S3 accepts ranges as https://www.w3.org/Protocols/rfc2616/rfc2616-sec14.html#sec14.35
         // and needs both ends to be exclusive
@@ -598,31 +680,39 @@ impl RemoteStorage for S3Bucket {
             None => format!("bytes={start_inclusive}-"),
         });
 
-        self.download_object(GetObjectRequest {
-            bucket: self.bucket_name.clone(),
-            key: self.relative_path_to_s3_object(from),
-            range,
-        })
+        self.download_object(
+            GetObjectRequest {
+                bucket: self.bucket_name.clone(),
+                key: self.relative_path_to_s3_object(from),
+                range,
+            },
+            cancel,
+        )
         .await
     }
-    async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()> {
-        let kind = RequestKind::Delete;
-        let _guard = self.permit(kind).await;
 
+    async fn delete_objects<'a>(
+        &self,
+        paths: &'a [RemotePath],
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
+        let kind = RequestKind::Delete;
+        let permit = self.permit(kind, cancel).await?;
         let mut delete_objects = Vec::with_capacity(paths.len());
         for path in paths {
             let obj_id = ObjectIdentifier::builder()
                 .set_key(Some(self.relative_path_to_s3_object(path)))
-                .build()?;
+                .build()
+                .context("convert path to oid")?;
             delete_objects.push(obj_id);
         }
 
-        self.delete_oids(kind, &delete_objects).await
+        self.delete_oids(&permit, &delete_objects, cancel).await
     }
 
-    async fn delete(&self, path: &RemotePath) -> anyhow::Result<()> {
+    async fn delete(&self, path: &RemotePath, cancel: &CancellationToken) -> anyhow::Result<()> {
         let paths = std::array::from_ref(path);
-        self.delete_objects(paths).await
+        self.delete_objects(paths, cancel).await
     }
 
     async fn time_travel_recover(
@@ -633,7 +723,7 @@ impl RemoteStorage for S3Bucket {
         cancel: &CancellationToken,
     ) -> Result<(), TimeTravelError> {
         let kind = RequestKind::TimeTravel;
-        let _guard = self.permit(kind).await;
+        let permit = self.permit(kind, cancel).await?;
 
         let timestamp = DateTime::from(timestamp);
         let done_if_after = DateTime::from(done_if_after);
@@ -647,7 +737,7 @@ impl RemoteStorage for S3Bucket {
 
         let warn_threshold = 3;
         let max_retries = 10;
-        let is_permanent = |_e: &_| false;
+        let is_permanent = |e: &_| matches!(e, TimeTravelError::Cancelled);
 
         let mut key_marker = None;
         let mut version_id_marker = None;
@@ -656,15 +746,19 @@ impl RemoteStorage for S3Bucket {
         loop {
             let response = backoff::retry(
                 || async {
-                    self.client
+                    let op = self
+                        .client
                         .list_object_versions()
                         .bucket(self.bucket_name.clone())
                         .set_prefix(prefix.clone())
                         .set_key_marker(key_marker.clone())
                         .set_version_id_marker(version_id_marker.clone())
-                        .send()
-                        .await
-                        .map_err(|e| TimeTravelError::Other(e.into()))
+                        .send();
+
+                    tokio::select! {
+                        res = op => res.map_err(|e| TimeTravelError::Other(e.into())),
+                        _ = cancel.cancelled() => Err(TimeTravelError::Cancelled),
+                    }
                 },
                 is_permanent,
                 warn_threshold,
@@ -786,14 +880,18 @@ impl RemoteStorage for S3Bucket {
 
                         backoff::retry(
                             || async {
-                                self.client
+                                let op = self
+                                    .client
                                     .copy_object()
                                     .bucket(self.bucket_name.clone())
                                     .key(key)
                                     .copy_source(&source_id)
-                                    .send()
-                                    .await
-                                    .map_err(|e| TimeTravelError::Other(e.into()))
+                                    .send();
+
+                                tokio::select! {
+                                    res = op => res.map_err(|e| TimeTravelError::Other(e.into())),
+                                    _ = cancel.cancelled() => Err(TimeTravelError::Cancelled),
+                                }
                             },
                             is_permanent,
                             warn_threshold,
@@ -824,10 +922,18 @@ impl RemoteStorage for S3Bucket {
                     let oid = ObjectIdentifier::builder()
                         .key(key.to_owned())
                         .build()
-                        .map_err(|e| TimeTravelError::Other(anyhow::Error::new(e)))?;
-                    self.delete_oids(kind, &[oid])
+                        .map_err(|e| TimeTravelError::Other(e.into()))?;
+
+                    self.delete_oids(&permit, &[oid], cancel)
                         .await
-                        .map_err(TimeTravelError::Other)?;
+                        .map_err(|e| {
+                            // delete_oid0 will use TimeoutOrCancel
+                            if TimeoutOrCancel::caused_by_cancel(&e) {
+                                TimeTravelError::Cancelled
+                            } else {
+                                TimeTravelError::Other(e)
+                            }
+                        })?;
                 }
             }
         }
@@ -963,7 +1069,8 @@ mod tests {
                 concurrency_limit: NonZeroUsize::new(100).unwrap(),
                 max_keys_per_list_response: Some(5),
             };
-            let storage = S3Bucket::new(&config).expect("remote storage init");
+            let storage =
+                S3Bucket::new(&config, std::time::Duration::ZERO).expect("remote storage init");
             for (test_path_idx, test_path) in all_paths.iter().enumerate() {
                 let result = storage.relative_path_to_s3_object(test_path);
                 let expected = expected_outputs[prefix_idx][test_path_idx];
diff --git a/libs/remote_storage/src/simulate_failures.rs b/libs/remote_storage/src/simulate_failures.rs
index 3dfa16b64e..f5344d3ae2 100644
--- a/libs/remote_storage/src/simulate_failures.rs
+++ b/libs/remote_storage/src/simulate_failures.rs
@@ -90,11 +90,16 @@ impl UnreliableWrapper {
         }
     }
 
-    async fn delete_inner(&self, path: &RemotePath, attempt: bool) -> anyhow::Result<()> {
+    async fn delete_inner(
+        &self,
+        path: &RemotePath,
+        attempt: bool,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         if attempt {
             self.attempt(RemoteOp::Delete(path.clone()))?;
         }
-        self.inner.delete(path).await
+        self.inner.delete(path, cancel).await
     }
 }
 
@@ -105,20 +110,22 @@ impl RemoteStorage for UnreliableWrapper {
     async fn list_prefixes(
         &self,
         prefix: Option<&RemotePath>,
+        cancel: &CancellationToken,
     ) -> Result<Vec<RemotePath>, DownloadError> {
         self.attempt(RemoteOp::ListPrefixes(prefix.cloned()))
             .map_err(DownloadError::Other)?;
-        self.inner.list_prefixes(prefix).await
+        self.inner.list_prefixes(prefix, cancel).await
     }
 
     async fn list_files(
         &self,
         folder: Option<&RemotePath>,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> Result<Vec<RemotePath>, DownloadError> {
         self.attempt(RemoteOp::ListPrefixes(folder.cloned()))
             .map_err(DownloadError::Other)?;
-        self.inner.list_files(folder, max_keys).await
+        self.inner.list_files(folder, max_keys, cancel).await
     }
 
     async fn list(
@@ -126,10 +133,11 @@ impl RemoteStorage for UnreliableWrapper {
         prefix: Option<&RemotePath>,
         mode: ListingMode,
         max_keys: Option<NonZeroU32>,
+        cancel: &CancellationToken,
     ) -> Result<Listing, DownloadError> {
         self.attempt(RemoteOp::ListPrefixes(prefix.cloned()))
             .map_err(DownloadError::Other)?;
-        self.inner.list(prefix, mode, max_keys).await
+        self.inner.list(prefix, mode, max_keys, cancel).await
     }
 
     async fn upload(
@@ -140,15 +148,22 @@ impl RemoteStorage for UnreliableWrapper {
         data_size_bytes: usize,
         to: &RemotePath,
         metadata: Option<StorageMetadata>,
+        cancel: &CancellationToken,
     ) -> anyhow::Result<()> {
         self.attempt(RemoteOp::Upload(to.clone()))?;
-        self.inner.upload(data, data_size_bytes, to, metadata).await
+        self.inner
+            .upload(data, data_size_bytes, to, metadata, cancel)
+            .await
     }
 
-    async fn download(&self, from: &RemotePath) -> Result<Download, DownloadError> {
+    async fn download(
+        &self,
+        from: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> Result<Download, DownloadError> {
         self.attempt(RemoteOp::Download(from.clone()))
             .map_err(DownloadError::Other)?;
-        self.inner.download(from).await
+        self.inner.download(from, cancel).await
     }
 
     async fn download_byte_range(
@@ -156,6 +171,7 @@ impl RemoteStorage for UnreliableWrapper {
         from: &RemotePath,
         start_inclusive: u64,
         end_exclusive: Option<u64>,
+        cancel: &CancellationToken,
     ) -> Result<Download, DownloadError> {
         // Note: We treat any download_byte_range as an "attempt" of the same
         // operation. We don't pay attention to the ranges. That's good enough
@@ -163,20 +179,24 @@ impl RemoteStorage for UnreliableWrapper {
         self.attempt(RemoteOp::Download(from.clone()))
             .map_err(DownloadError::Other)?;
         self.inner
-            .download_byte_range(from, start_inclusive, end_exclusive)
+            .download_byte_range(from, start_inclusive, end_exclusive, cancel)
             .await
     }
 
-    async fn delete(&self, path: &RemotePath) -> anyhow::Result<()> {
-        self.delete_inner(path, true).await
+    async fn delete(&self, path: &RemotePath, cancel: &CancellationToken) -> anyhow::Result<()> {
+        self.delete_inner(path, true, cancel).await
     }
 
-    async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()> {
+    async fn delete_objects<'a>(
+        &self,
+        paths: &'a [RemotePath],
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         self.attempt(RemoteOp::DeleteObjects(paths.to_vec()))?;
         let mut error_counter = 0;
         for path in paths {
             // Dont record attempt because it was already recorded above
-            if (self.delete_inner(path, false).await).is_err() {
+            if (self.delete_inner(path, false, cancel).await).is_err() {
                 error_counter += 1;
             }
         }
@@ -189,11 +209,16 @@ impl RemoteStorage for UnreliableWrapper {
         Ok(())
     }
 
-    async fn copy(&self, from: &RemotePath, to: &RemotePath) -> anyhow::Result<()> {
+    async fn copy(
+        &self,
+        from: &RemotePath,
+        to: &RemotePath,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<()> {
         // copy is equivalent to download + upload
         self.attempt(RemoteOp::Download(from.clone()))?;
         self.attempt(RemoteOp::Upload(to.clone()))?;
-        self.inner.copy_object(from, to).await
+        self.inner.copy_object(from, to, cancel).await
     }
 
     async fn time_travel_recover(
diff --git a/libs/remote_storage/src/support.rs b/libs/remote_storage/src/support.rs
index 4688a484a5..20f193c6c8 100644
--- a/libs/remote_storage/src/support.rs
+++ b/libs/remote_storage/src/support.rs
@@ -1,9 +1,15 @@
 use std::{
+    future::Future,
     pin::Pin,
     task::{Context, Poll},
+    time::Duration,
 };
 
+use bytes::Bytes;
 use futures_util::Stream;
+use tokio_util::sync::CancellationToken;
+
+use crate::TimeoutOrCancel;
 
 pin_project_lite::pin_project! {
     /// An `AsyncRead` adapter which carries a permit for the lifetime of the value.
@@ -31,3 +37,133 @@ impl<S: Stream> Stream for PermitCarrying<S> {
         self.inner.size_hint()
     }
 }
+
+pin_project_lite::pin_project! {
+    pub(crate) struct DownloadStream<F, S> {
+        hit: bool,
+        #[pin]
+        cancellation: F,
+        #[pin]
+        inner: S,
+    }
+}
+
+impl<F, S> DownloadStream<F, S> {
+    pub(crate) fn new(cancellation: F, inner: S) -> Self {
+        Self {
+            cancellation,
+            hit: false,
+            inner,
+        }
+    }
+}
+
+/// See documentation on [`crate::DownloadStream`] on rationale why `std::io::Error` is used.
+impl<E, F, S> Stream for DownloadStream<F, S>
+where
+    std::io::Error: From<E>,
+    F: Future<Output = E>,
+    S: Stream<Item = std::io::Result<Bytes>>,
+{
+    type Item = <S as Stream>::Item;
+
+    fn poll_next(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Option<Self::Item>> {
+        let this = self.project();
+
+        if !*this.hit {
+            if let Poll::Ready(e) = this.cancellation.poll(cx) {
+                *this.hit = true;
+                let e = Err(std::io::Error::from(e));
+                return Poll::Ready(Some(e));
+            }
+        }
+
+        this.inner.poll_next(cx)
+    }
+
+    fn size_hint(&self) -> (usize, Option<usize>) {
+        self.inner.size_hint()
+    }
+}
+
+/// Fires only on the first cancel or timeout, not on both.
+pub(crate) async fn cancel_or_timeout(
+    timeout: Duration,
+    cancel: CancellationToken,
+) -> TimeoutOrCancel {
+    tokio::select! {
+        _ = tokio::time::sleep(timeout) => TimeoutOrCancel::Timeout,
+        _ = cancel.cancelled() => TimeoutOrCancel::Cancel,
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::DownloadError;
+    use futures::stream::StreamExt;
+
+    #[tokio::test(start_paused = true)]
+    async fn cancelled_download_stream() {
+        let inner = futures::stream::pending();
+        let timeout = Duration::from_secs(120);
+        let cancel = CancellationToken::new();
+
+        let stream = DownloadStream::new(cancel_or_timeout(timeout, cancel.clone()), inner);
+        let mut stream = std::pin::pin!(stream);
+
+        let mut first = stream.next();
+
+        tokio::select! {
+            _ = &mut first => unreachable!("we haven't yet cancelled nor is timeout passed"),
+            _ = tokio::time::sleep(Duration::from_secs(1)) => {},
+        }
+
+        cancel.cancel();
+
+        let e = first.await.expect("there must be some").unwrap_err();
+        assert!(matches!(e.kind(), std::io::ErrorKind::Other), "{e:?}");
+        let inner = e.get_ref().expect("inner should be set");
+        assert!(
+            inner
+                .downcast_ref::<DownloadError>()
+                .is_some_and(|e| matches!(e, DownloadError::Cancelled)),
+            "{inner:?}"
+        );
+
+        tokio::select! {
+            _ = stream.next() => unreachable!("no timeout ever happens as we were already cancelled"),
+            _ = tokio::time::sleep(Duration::from_secs(121)) => {},
+        }
+    }
+
+    #[tokio::test(start_paused = true)]
+    async fn timeouted_download_stream() {
+        let inner = futures::stream::pending();
+        let timeout = Duration::from_secs(120);
+        let cancel = CancellationToken::new();
+
+        let stream = DownloadStream::new(cancel_or_timeout(timeout, cancel.clone()), inner);
+        let mut stream = std::pin::pin!(stream);
+
+        // because the stream uses 120s timeout we are paused, we advance to 120s right away.
+        let first = stream.next();
+
+        let e = first.await.expect("there must be some").unwrap_err();
+        assert!(matches!(e.kind(), std::io::ErrorKind::Other), "{e:?}");
+        let inner = e.get_ref().expect("inner should be set");
+        assert!(
+            inner
+                .downcast_ref::<DownloadError>()
+                .is_some_and(|e| matches!(e, DownloadError::Timeout)),
+            "{inner:?}"
+        );
+
+        cancel.cancel();
+
+        tokio::select! {
+            _ = stream.next() => unreachable!("no cancellation ever happens because we already timed out"),
+            _ = tokio::time::sleep(Duration::from_secs(121)) => {},
+        }
+    }
+}
diff --git a/libs/remote_storage/tests/common/mod.rs b/libs/remote_storage/tests/common/mod.rs
index bca117ed1a..da9dc08d8d 100644
--- a/libs/remote_storage/tests/common/mod.rs
+++ b/libs/remote_storage/tests/common/mod.rs
@@ -10,6 +10,7 @@ use futures::stream::Stream;
 use once_cell::sync::OnceCell;
 use remote_storage::{Download, GenericRemoteStorage, RemotePath};
 use tokio::task::JoinSet;
+use tokio_util::sync::CancellationToken;
 use tracing::{debug, error, info};
 
 static LOGGING_DONE: OnceCell<()> = OnceCell::new();
@@ -58,8 +59,12 @@ pub(crate) async fn upload_simple_remote_data(
 ) -> ControlFlow<HashSet<RemotePath>, HashSet<RemotePath>> {
     info!("Creating {upload_tasks_count} remote files");
     let mut upload_tasks = JoinSet::new();
+    let cancel = CancellationToken::new();
+
     for i in 1..upload_tasks_count + 1 {
         let task_client = Arc::clone(client);
+        let cancel = cancel.clone();
+
         upload_tasks.spawn(async move {
             let blob_path = PathBuf::from(format!("folder{}/blob_{}.txt", i / 7, i));
             let blob_path = RemotePath::new(
@@ -69,7 +74,9 @@ pub(crate) async fn upload_simple_remote_data(
             debug!("Creating remote item {i} at path {blob_path:?}");
 
             let (data, len) = upload_stream(format!("remote blob data {i}").into_bytes().into());
-            task_client.upload(data, len, &blob_path, None).await?;
+            task_client
+                .upload(data, len, &blob_path, None, &cancel)
+                .await?;
 
             Ok::<_, anyhow::Error>(blob_path)
         });
@@ -107,13 +114,15 @@ pub(crate) async fn cleanup(
         "Removing {} objects from the remote storage during cleanup",
         objects_to_delete.len()
     );
+    let cancel = CancellationToken::new();
     let mut delete_tasks = JoinSet::new();
     for object_to_delete in objects_to_delete {
         let task_client = Arc::clone(client);
+        let cancel = cancel.clone();
         delete_tasks.spawn(async move {
             debug!("Deleting remote item at path {object_to_delete:?}");
             task_client
-                .delete(&object_to_delete)
+                .delete(&object_to_delete, &cancel)
                 .await
                 .with_context(|| format!("{object_to_delete:?} removal"))
         });
@@ -141,8 +150,12 @@ pub(crate) async fn upload_remote_data(
 ) -> ControlFlow<Uploads, Uploads> {
     info!("Creating {upload_tasks_count} remote files");
     let mut upload_tasks = JoinSet::new();
+    let cancel = CancellationToken::new();
+
     for i in 1..upload_tasks_count + 1 {
         let task_client = Arc::clone(client);
+        let cancel = cancel.clone();
+
         upload_tasks.spawn(async move {
             let prefix = format!("{base_prefix_str}/sub_prefix_{i}/");
             let blob_prefix = RemotePath::new(Utf8Path::new(&prefix))
@@ -152,7 +165,9 @@ pub(crate) async fn upload_remote_data(
 
             let (data, data_len) =
                 upload_stream(format!("remote blob data {i}").into_bytes().into());
-            task_client.upload(data, data_len, &blob_path, None).await?;
+            task_client
+                .upload(data, data_len, &blob_path, None, &cancel)
+                .await?;
 
             Ok::<_, anyhow::Error>((blob_prefix, blob_path))
         });
diff --git a/libs/remote_storage/tests/common/tests.rs b/libs/remote_storage/tests/common/tests.rs
index 6d062f3898..72f6f956e0 100644
--- a/libs/remote_storage/tests/common/tests.rs
+++ b/libs/remote_storage/tests/common/tests.rs
@@ -4,6 +4,7 @@ use remote_storage::RemotePath;
 use std::sync::Arc;
 use std::{collections::HashSet, num::NonZeroU32};
 use test_context::test_context;
+use tokio_util::sync::CancellationToken;
 use tracing::debug;
 
 use crate::common::{download_to_vec, upload_stream, wrap_stream};
@@ -45,13 +46,15 @@ async fn pagination_should_work(ctx: &mut MaybeEnabledStorageWithTestBlobs) -> a
         }
     };
 
+    let cancel = CancellationToken::new();
+
     let test_client = Arc::clone(&ctx.enabled.client);
     let expected_remote_prefixes = ctx.remote_prefixes.clone();
 
     let base_prefix = RemotePath::new(Utf8Path::new(ctx.enabled.base_prefix))
         .context("common_prefix construction")?;
     let root_remote_prefixes = test_client
-        .list_prefixes(None)
+        .list_prefixes(None, &cancel)
         .await
         .context("client list root prefixes failure")?
         .into_iter()
@@ -62,7 +65,7 @@ async fn pagination_should_work(ctx: &mut MaybeEnabledStorageWithTestBlobs) -> a
     );
 
     let nested_remote_prefixes = test_client
-        .list_prefixes(Some(&base_prefix))
+        .list_prefixes(Some(&base_prefix), &cancel)
         .await
         .context("client list nested prefixes failure")?
         .into_iter()
@@ -99,11 +102,12 @@ async fn list_files_works(ctx: &mut MaybeEnabledStorageWithSimpleTestBlobs) -> a
             anyhow::bail!("S3 init failed: {e:?}")
         }
     };
+    let cancel = CancellationToken::new();
     let test_client = Arc::clone(&ctx.enabled.client);
     let base_prefix =
         RemotePath::new(Utf8Path::new("folder1")).context("common_prefix construction")?;
     let root_files = test_client
-        .list_files(None, None)
+        .list_files(None, None, &cancel)
         .await
         .context("client list root files failure")?
         .into_iter()
@@ -117,13 +121,13 @@ async fn list_files_works(ctx: &mut MaybeEnabledStorageWithSimpleTestBlobs) -> a
     // Test that max_keys limit works. In total there are about 21 files (see
     // upload_simple_remote_data call in test_real_s3.rs).
     let limited_root_files = test_client
-        .list_files(None, Some(NonZeroU32::new(2).unwrap()))
+        .list_files(None, Some(NonZeroU32::new(2).unwrap()), &cancel)
         .await
         .context("client list root files failure")?;
     assert_eq!(limited_root_files.len(), 2);
 
     let nested_remote_files = test_client
-        .list_files(Some(&base_prefix), None)
+        .list_files(Some(&base_prefix), None, &cancel)
         .await
         .context("client list nested files failure")?
         .into_iter()
@@ -150,12 +154,17 @@ async fn delete_non_exising_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Resu
         MaybeEnabledStorage::Disabled => return Ok(()),
     };
 
+    let cancel = CancellationToken::new();
+
     let path = RemotePath::new(Utf8Path::new(
         format!("{}/for_sure_there_is_nothing_there_really", ctx.base_prefix).as_str(),
     ))
     .with_context(|| "RemotePath conversion")?;
 
-    ctx.client.delete(&path).await.expect("should succeed");
+    ctx.client
+        .delete(&path, &cancel)
+        .await
+        .expect("should succeed");
 
     Ok(())
 }
@@ -168,6 +177,8 @@ async fn delete_objects_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Result<(
         MaybeEnabledStorage::Disabled => return Ok(()),
     };
 
+    let cancel = CancellationToken::new();
+
     let path1 = RemotePath::new(Utf8Path::new(format!("{}/path1", ctx.base_prefix).as_str()))
         .with_context(|| "RemotePath conversion")?;
 
@@ -178,21 +189,21 @@ async fn delete_objects_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Result<(
         .with_context(|| "RemotePath conversion")?;
 
     let (data, len) = upload_stream("remote blob data1".as_bytes().into());
-    ctx.client.upload(data, len, &path1, None).await?;
+    ctx.client.upload(data, len, &path1, None, &cancel).await?;
 
     let (data, len) = upload_stream("remote blob data2".as_bytes().into());
-    ctx.client.upload(data, len, &path2, None).await?;
+    ctx.client.upload(data, len, &path2, None, &cancel).await?;
 
     let (data, len) = upload_stream("remote blob data3".as_bytes().into());
-    ctx.client.upload(data, len, &path3, None).await?;
+    ctx.client.upload(data, len, &path3, None, &cancel).await?;
 
-    ctx.client.delete_objects(&[path1, path2]).await?;
+    ctx.client.delete_objects(&[path1, path2], &cancel).await?;
 
-    let prefixes = ctx.client.list_prefixes(None).await?;
+    let prefixes = ctx.client.list_prefixes(None, &cancel).await?;
 
     assert_eq!(prefixes.len(), 1);
 
-    ctx.client.delete_objects(&[path3]).await?;
+    ctx.client.delete_objects(&[path3], &cancel).await?;
 
     Ok(())
 }
@@ -204,6 +215,8 @@ async fn upload_download_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Result<
         return Ok(());
     };
 
+    let cancel = CancellationToken::new();
+
     let path = RemotePath::new(Utf8Path::new(format!("{}/file", ctx.base_prefix).as_str()))
         .with_context(|| "RemotePath conversion")?;
 
@@ -211,47 +224,56 @@ async fn upload_download_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Result<
 
     let (data, len) = wrap_stream(orig.clone());
 
-    ctx.client.upload(data, len, &path, None).await?;
+    ctx.client.upload(data, len, &path, None, &cancel).await?;
 
     // Normal download request
-    let dl = ctx.client.download(&path).await?;
+    let dl = ctx.client.download(&path, &cancel).await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig);
 
     // Full range (end specified)
     let dl = ctx
         .client
-        .download_byte_range(&path, 0, Some(len as u64))
+        .download_byte_range(&path, 0, Some(len as u64), &cancel)
         .await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig);
 
     // partial range (end specified)
-    let dl = ctx.client.download_byte_range(&path, 4, Some(10)).await?;
+    let dl = ctx
+        .client
+        .download_byte_range(&path, 4, Some(10), &cancel)
+        .await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig[4..10]);
 
     // partial range (end beyond real end)
     let dl = ctx
         .client
-        .download_byte_range(&path, 8, Some(len as u64 * 100))
+        .download_byte_range(&path, 8, Some(len as u64 * 100), &cancel)
         .await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig[8..]);
 
     // Partial range (end unspecified)
-    let dl = ctx.client.download_byte_range(&path, 4, None).await?;
+    let dl = ctx
+        .client
+        .download_byte_range(&path, 4, None, &cancel)
+        .await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig[4..]);
 
     // Full range (end unspecified)
-    let dl = ctx.client.download_byte_range(&path, 0, None).await?;
+    let dl = ctx
+        .client
+        .download_byte_range(&path, 0, None, &cancel)
+        .await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig);
 
     debug!("Cleanup: deleting file at path {path:?}");
     ctx.client
-        .delete(&path)
+        .delete(&path, &cancel)
         .await
         .with_context(|| format!("{path:?} removal"))?;
 
@@ -265,6 +287,8 @@ async fn copy_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Result<()> {
         return Ok(());
     };
 
+    let cancel = CancellationToken::new();
+
     let path = RemotePath::new(Utf8Path::new(
         format!("{}/file_to_copy", ctx.base_prefix).as_str(),
     ))
@@ -278,18 +302,18 @@ async fn copy_works(ctx: &mut MaybeEnabledStorage) -> anyhow::Result<()> {
 
     let (data, len) = wrap_stream(orig.clone());
 
-    ctx.client.upload(data, len, &path, None).await?;
+    ctx.client.upload(data, len, &path, None, &cancel).await?;
 
     // Normal download request
-    ctx.client.copy_object(&path, &path_dest).await?;
+    ctx.client.copy_object(&path, &path_dest, &cancel).await?;
 
-    let dl = ctx.client.download(&path_dest).await?;
+    let dl = ctx.client.download(&path_dest, &cancel).await?;
     let buf = download_to_vec(dl).await?;
     assert_eq!(&buf, &orig);
 
     debug!("Cleanup: deleting file at path {path:?}");
     ctx.client
-        .delete_objects(&[path.clone(), path_dest.clone()])
+        .delete_objects(&[path.clone(), path_dest.clone()], &cancel)
         .await
         .with_context(|| format!("{path:?} removal"))?;
 
diff --git a/libs/remote_storage/tests/test_real_azure.rs b/libs/remote_storage/tests/test_real_azure.rs
index 6f9a1ec6f7..6adddf52a9 100644
--- a/libs/remote_storage/tests/test_real_azure.rs
+++ b/libs/remote_storage/tests/test_real_azure.rs
@@ -1,9 +1,9 @@
-use std::collections::HashSet;
 use std::env;
 use std::num::NonZeroUsize;
 use std::ops::ControlFlow;
 use std::sync::Arc;
 use std::time::UNIX_EPOCH;
+use std::{collections::HashSet, time::Duration};
 
 use anyhow::Context;
 use remote_storage::{
@@ -39,6 +39,17 @@ impl EnabledAzure {
             base_prefix: BASE_PREFIX,
         }
     }
+
+    #[allow(unused)] // this will be needed when moving the timeout integration tests back
+    fn configure_request_timeout(&mut self, timeout: Duration) {
+        match Arc::get_mut(&mut self.client).expect("outer Arc::get_mut") {
+            GenericRemoteStorage::AzureBlob(azure) => {
+                let azure = Arc::get_mut(azure).expect("inner Arc::get_mut");
+                azure.timeout = timeout;
+            }
+            _ => unreachable!(),
+        }
+    }
 }
 
 enum MaybeEnabledStorage {
@@ -213,6 +224,7 @@ fn create_azure_client(
             concurrency_limit: NonZeroUsize::new(100).unwrap(),
             max_keys_per_list_response,
         }),
+        timeout: Duration::from_secs(120),
     };
     Ok(Arc::new(
         GenericRemoteStorage::from_config(&remote_storage_config).context("remote storage init")?,
diff --git a/libs/remote_storage/tests/test_real_s3.rs b/libs/remote_storage/tests/test_real_s3.rs
index 3dc8347c83..e927b40e80 100644
--- a/libs/remote_storage/tests/test_real_s3.rs
+++ b/libs/remote_storage/tests/test_real_s3.rs
@@ -1,5 +1,6 @@
 use std::env;
 use std::fmt::{Debug, Display};
+use std::future::Future;
 use std::num::NonZeroUsize;
 use std::ops::ControlFlow;
 use std::sync::Arc;
@@ -9,9 +10,10 @@ use std::{collections::HashSet, time::SystemTime};
 use crate::common::{download_to_vec, upload_stream};
 use anyhow::Context;
 use camino::Utf8Path;
-use futures_util::Future;
+use futures_util::StreamExt;
 use remote_storage::{
-    GenericRemoteStorage, RemotePath, RemoteStorageConfig, RemoteStorageKind, S3Config,
+    DownloadError, GenericRemoteStorage, RemotePath, RemoteStorageConfig, RemoteStorageKind,
+    S3Config,
 };
 use test_context::test_context;
 use test_context::AsyncTestContext;
@@ -27,7 +29,6 @@ use common::{cleanup, ensure_logging_ready, upload_remote_data, upload_simple_re
 use utils::backoff;
 
 const ENABLE_REAL_S3_REMOTE_STORAGE_ENV_VAR_NAME: &str = "ENABLE_REAL_S3_REMOTE_STORAGE";
-
 const BASE_PREFIX: &str = "test";
 
 #[test_context(MaybeEnabledStorage)]
@@ -69,8 +70,11 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
         ret
     }
 
-    async fn list_files(client: &Arc<GenericRemoteStorage>) -> anyhow::Result<HashSet<RemotePath>> {
-        Ok(retry(|| client.list_files(None, None))
+    async fn list_files(
+        client: &Arc<GenericRemoteStorage>,
+        cancel: &CancellationToken,
+    ) -> anyhow::Result<HashSet<RemotePath>> {
+        Ok(retry(|| client.list_files(None, None, cancel))
             .await
             .context("list root files failure")?
             .into_iter()
@@ -90,11 +94,11 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
 
     retry(|| {
         let (data, len) = upload_stream("remote blob data1".as_bytes().into());
-        ctx.client.upload(data, len, &path1, None)
+        ctx.client.upload(data, len, &path1, None, &cancel)
     })
     .await?;
 
-    let t0_files = list_files(&ctx.client).await?;
+    let t0_files = list_files(&ctx.client, &cancel).await?;
     let t0 = time_point().await;
     println!("at t0: {t0_files:?}");
 
@@ -102,17 +106,17 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
 
     retry(|| {
         let (data, len) = upload_stream(old_data.as_bytes().into());
-        ctx.client.upload(data, len, &path2, None)
+        ctx.client.upload(data, len, &path2, None, &cancel)
     })
     .await?;
 
-    let t1_files = list_files(&ctx.client).await?;
+    let t1_files = list_files(&ctx.client, &cancel).await?;
     let t1 = time_point().await;
     println!("at t1: {t1_files:?}");
 
     // A little check to ensure that our clock is not too far off from the S3 clock
     {
-        let dl = retry(|| ctx.client.download(&path2)).await?;
+        let dl = retry(|| ctx.client.download(&path2, &cancel)).await?;
         let last_modified = dl.last_modified.unwrap();
         let half_wt = WAIT_TIME.mul_f32(0.5);
         let t0_hwt = t0 + half_wt;
@@ -125,7 +129,7 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
 
     retry(|| {
         let (data, len) = upload_stream("remote blob data3".as_bytes().into());
-        ctx.client.upload(data, len, &path3, None)
+        ctx.client.upload(data, len, &path3, None, &cancel)
     })
     .await?;
 
@@ -133,12 +137,12 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
 
     retry(|| {
         let (data, len) = upload_stream(new_data.as_bytes().into());
-        ctx.client.upload(data, len, &path2, None)
+        ctx.client.upload(data, len, &path2, None, &cancel)
     })
     .await?;
 
-    retry(|| ctx.client.delete(&path1)).await?;
-    let t2_files = list_files(&ctx.client).await?;
+    retry(|| ctx.client.delete(&path1, &cancel)).await?;
+    let t2_files = list_files(&ctx.client, &cancel).await?;
     let t2 = time_point().await;
     println!("at t2: {t2_files:?}");
 
@@ -147,10 +151,10 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
     ctx.client
         .time_travel_recover(None, t2, t_final, &cancel)
         .await?;
-    let t2_files_recovered = list_files(&ctx.client).await?;
+    let t2_files_recovered = list_files(&ctx.client, &cancel).await?;
     println!("after recovery to t2: {t2_files_recovered:?}");
     assert_eq!(t2_files, t2_files_recovered);
-    let path2_recovered_t2 = download_to_vec(ctx.client.download(&path2).await?).await?;
+    let path2_recovered_t2 = download_to_vec(ctx.client.download(&path2, &cancel).await?).await?;
     assert_eq!(path2_recovered_t2, new_data.as_bytes());
 
     // after recovery to t1: path1 is back, path2 has the old content
@@ -158,10 +162,10 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
     ctx.client
         .time_travel_recover(None, t1, t_final, &cancel)
         .await?;
-    let t1_files_recovered = list_files(&ctx.client).await?;
+    let t1_files_recovered = list_files(&ctx.client, &cancel).await?;
     println!("after recovery to t1: {t1_files_recovered:?}");
     assert_eq!(t1_files, t1_files_recovered);
-    let path2_recovered_t1 = download_to_vec(ctx.client.download(&path2).await?).await?;
+    let path2_recovered_t1 = download_to_vec(ctx.client.download(&path2, &cancel).await?).await?;
     assert_eq!(path2_recovered_t1, old_data.as_bytes());
 
     // after recovery to t0: everything is gone except for path1
@@ -169,14 +173,14 @@ async fn s3_time_travel_recovery_works(ctx: &mut MaybeEnabledStorage) -> anyhow:
     ctx.client
         .time_travel_recover(None, t0, t_final, &cancel)
         .await?;
-    let t0_files_recovered = list_files(&ctx.client).await?;
+    let t0_files_recovered = list_files(&ctx.client, &cancel).await?;
     println!("after recovery to t0: {t0_files_recovered:?}");
     assert_eq!(t0_files, t0_files_recovered);
 
     // cleanup
 
     let paths = &[path1, path2, path3];
-    retry(|| ctx.client.delete_objects(paths)).await?;
+    retry(|| ctx.client.delete_objects(paths, &cancel)).await?;
 
     Ok(())
 }
@@ -197,6 +201,16 @@ impl EnabledS3 {
             base_prefix: BASE_PREFIX,
         }
     }
+
+    fn configure_request_timeout(&mut self, timeout: Duration) {
+        match Arc::get_mut(&mut self.client).expect("outer Arc::get_mut") {
+            GenericRemoteStorage::AwsS3(s3) => {
+                let s3 = Arc::get_mut(s3).expect("inner Arc::get_mut");
+                s3.timeout = timeout;
+            }
+            _ => unreachable!(),
+        }
+    }
 }
 
 enum MaybeEnabledStorage {
@@ -370,8 +384,169 @@ fn create_s3_client(
             concurrency_limit: NonZeroUsize::new(100).unwrap(),
             max_keys_per_list_response,
         }),
+        timeout: RemoteStorageConfig::DEFAULT_TIMEOUT,
     };
     Ok(Arc::new(
         GenericRemoteStorage::from_config(&remote_storage_config).context("remote storage init")?,
     ))
 }
+
+#[test_context(MaybeEnabledStorage)]
+#[tokio::test]
+async fn download_is_timeouted(ctx: &mut MaybeEnabledStorage) {
+    let MaybeEnabledStorage::Enabled(ctx) = ctx else {
+        return;
+    };
+
+    let cancel = CancellationToken::new();
+
+    let path = RemotePath::new(Utf8Path::new(
+        format!("{}/file_to_copy", ctx.base_prefix).as_str(),
+    ))
+    .unwrap();
+
+    let len = upload_large_enough_file(&ctx.client, &path, &cancel).await;
+
+    let timeout = std::time::Duration::from_secs(5);
+
+    ctx.configure_request_timeout(timeout);
+
+    let started_at = std::time::Instant::now();
+    let mut stream = ctx
+        .client
+        .download(&path, &cancel)
+        .await
+        .expect("download succeeds")
+        .download_stream;
+
+    if started_at.elapsed().mul_f32(0.9) >= timeout {
+        tracing::warn!(
+            elapsed_ms = started_at.elapsed().as_millis(),
+            "timeout might be too low, consumed most of it during headers"
+        );
+    }
+
+    let first = stream
+        .next()
+        .await
+        .expect("should have the first blob")
+        .expect("should have succeeded");
+
+    tracing::info!(len = first.len(), "downloaded first chunk");
+
+    assert!(
+        first.len() < len,
+        "uploaded file is too small, we downloaded all on first chunk"
+    );
+
+    tokio::time::sleep(timeout).await;
+
+    {
+        let started_at = std::time::Instant::now();
+        let next = stream
+            .next()
+            .await
+            .expect("stream should not have ended yet");
+
+        tracing::info!(
+            next.is_err = next.is_err(),
+            elapsed_ms = started_at.elapsed().as_millis(),
+            "received item after timeout"
+        );
+
+        let e = next.expect_err("expected an error, but got a chunk?");
+
+        let inner = e.get_ref().expect("std::io::Error::inner should be set");
+        assert!(
+            inner
+                .downcast_ref::<DownloadError>()
+                .is_some_and(|e| matches!(e, DownloadError::Timeout)),
+            "{inner:?}"
+        );
+    }
+
+    ctx.configure_request_timeout(RemoteStorageConfig::DEFAULT_TIMEOUT);
+
+    ctx.client.delete_objects(&[path], &cancel).await.unwrap()
+}
+
+#[test_context(MaybeEnabledStorage)]
+#[tokio::test]
+async fn download_is_cancelled(ctx: &mut MaybeEnabledStorage) {
+    let MaybeEnabledStorage::Enabled(ctx) = ctx else {
+        return;
+    };
+
+    let cancel = CancellationToken::new();
+
+    let path = RemotePath::new(Utf8Path::new(
+        format!("{}/file_to_copy", ctx.base_prefix).as_str(),
+    ))
+    .unwrap();
+
+    let len = upload_large_enough_file(&ctx.client, &path, &cancel).await;
+
+    {
+        let mut stream = ctx
+            .client
+            .download(&path, &cancel)
+            .await
+            .expect("download succeeds")
+            .download_stream;
+
+        let first = stream
+            .next()
+            .await
+            .expect("should have the first blob")
+            .expect("should have succeeded");
+
+        tracing::info!(len = first.len(), "downloaded first chunk");
+
+        assert!(
+            first.len() < len,
+            "uploaded file is too small, we downloaded all on first chunk"
+        );
+
+        cancel.cancel();
+
+        let next = stream.next().await.expect("stream should have more");
+
+        let e = next.expect_err("expected an error, but got a chunk?");
+
+        let inner = e.get_ref().expect("std::io::Error::inner should be set");
+        assert!(
+            inner
+                .downcast_ref::<DownloadError>()
+                .is_some_and(|e| matches!(e, DownloadError::Cancelled)),
+            "{inner:?}"
+        );
+    }
+
+    let cancel = CancellationToken::new();
+
+    ctx.client.delete_objects(&[path], &cancel).await.unwrap();
+}
+
+/// Upload a long enough file so that we cannot download it in single chunk
+///
+/// For s3 the first chunk seems to be less than 10kB, so this has a bit of a safety margin
+async fn upload_large_enough_file(
+    client: &GenericRemoteStorage,
+    path: &RemotePath,
+    cancel: &CancellationToken,
+) -> usize {
+    let header = bytes::Bytes::from_static("remote blob data content".as_bytes());
+    let body = bytes::Bytes::from(vec![0u8; 1024]);
+    let contents = std::iter::once(header).chain(std::iter::repeat(body).take(128));
+
+    let len = contents.clone().fold(0, |acc, next| acc + next.len());
+
+    let contents = futures::stream::iter(contents.map(std::io::Result::Ok));
+
+    client
+        .upload(contents, len, path, None, cancel)
+        .await
+        .expect("upload succeeds");
+
+    len
+}
diff --git a/pageserver/src/config.rs b/pageserver/src/config.rs
index 1989bef817..6d71ff1dd4 100644
--- a/pageserver/src/config.rs
+++ b/pageserver/src/config.rs
@@ -1359,6 +1359,7 @@ broker_endpoint = '{broker_endpoint}'
                 parsed_remote_storage_config,
                 RemoteStorageConfig {
                     storage: RemoteStorageKind::LocalFs(local_storage_path.clone()),
+                    timeout: RemoteStorageConfig::DEFAULT_TIMEOUT,
                 },
                 "Remote storage config should correctly parse the local FS config and fill other storage defaults"
             );
@@ -1426,6 +1427,7 @@ broker_endpoint = '{broker_endpoint}'
                         concurrency_limit: s3_concurrency_limit,
                         max_keys_per_list_response: None,
                     }),
+                    timeout: RemoteStorageConfig::DEFAULT_TIMEOUT,
                 },
                 "Remote storage config should correctly parse the S3 config"
             );
diff --git a/pageserver/src/deletion_queue.rs b/pageserver/src/deletion_queue.rs
index 81938b14b3..62ba702db7 100644
--- a/pageserver/src/deletion_queue.rs
+++ b/pageserver/src/deletion_queue.rs
@@ -867,6 +867,7 @@ mod test {
         let remote_fs_dir = harness.conf.workdir.join("remote_fs").canonicalize_utf8()?;
         let storage_config = RemoteStorageConfig {
             storage: RemoteStorageKind::LocalFs(remote_fs_dir.clone()),
+            timeout: RemoteStorageConfig::DEFAULT_TIMEOUT,
         };
         let storage = GenericRemoteStorage::from_config(&storage_config).unwrap();
 
@@ -1170,6 +1171,7 @@ pub(crate) mod mock {
     pub struct ConsumerState {
         rx: tokio::sync::mpsc::UnboundedReceiver<ListWriterQueueMessage>,
         executor_rx: tokio::sync::mpsc::Receiver<DeleterMessage>,
+        cancel: CancellationToken,
     }
 
     impl ConsumerState {
@@ -1183,7 +1185,7 @@ pub(crate) mod mock {
                 match msg {
                     DeleterMessage::Delete(objects) => {
                         for path in objects {
-                            match remote_storage.delete(&path).await {
+                            match remote_storage.delete(&path, &self.cancel).await {
                                 Ok(_) => {
                                     debug!("Deleted {path}");
                                 }
@@ -1216,7 +1218,7 @@ pub(crate) mod mock {
 
                         for path in objects {
                             info!("Executing deletion {path}");
-                            match remote_storage.delete(&path).await {
+                            match remote_storage.delete(&path, &self.cancel).await {
                                 Ok(_) => {
                                     debug!("Deleted {path}");
                                 }
@@ -1266,7 +1268,11 @@ pub(crate) mod mock {
                 executor_tx,
                 executed,
                 remote_storage,
-                consumer: std::sync::Mutex::new(ConsumerState { rx, executor_rx }),
+                consumer: std::sync::Mutex::new(ConsumerState {
+                    rx,
+                    executor_rx,
+                    cancel: CancellationToken::new(),
+                }),
                 lsn_table: Arc::new(std::sync::RwLock::new(VisibleLsnUpdates::new())),
             }
         }
diff --git a/pageserver/src/deletion_queue/deleter.rs b/pageserver/src/deletion_queue/deleter.rs
index a75c73f2b1..1f04bc0410 100644
--- a/pageserver/src/deletion_queue/deleter.rs
+++ b/pageserver/src/deletion_queue/deleter.rs
@@ -8,6 +8,7 @@
 
 use remote_storage::GenericRemoteStorage;
 use remote_storage::RemotePath;
+use remote_storage::TimeoutOrCancel;
 use remote_storage::MAX_KEYS_PER_DELETE;
 use std::time::Duration;
 use tokio_util::sync::CancellationToken;
@@ -71,9 +72,11 @@ impl Deleter {
                     Err(anyhow::anyhow!("failpoint: deletion-queue-before-execute"))
                 });
 
-                self.remote_storage.delete_objects(&self.accumulator).await
+                self.remote_storage
+                    .delete_objects(&self.accumulator, &self.cancel)
+                    .await
             },
-            |_| false,
+            TimeoutOrCancel::caused_by_cancel,
             3,
             10,
             "executing deletion batch",
diff --git a/pageserver/src/tenant.rs b/pageserver/src/tenant.rs
index 88f4ae7086..e500a6123c 100644
--- a/pageserver/src/tenant.rs
+++ b/pageserver/src/tenant.rs
@@ -25,6 +25,7 @@ use pageserver_api::shard::ShardIdentity;
 use pageserver_api::shard::TenantShardId;
 use remote_storage::DownloadError;
 use remote_storage::GenericRemoteStorage;
+use remote_storage::TimeoutOrCancel;
 use std::fmt;
 use storage_broker::BrokerClientChannel;
 use tokio::io::BufReader;
@@ -3339,7 +3340,7 @@ impl Tenant {
             &self.cancel,
         )
         .await
-        .ok_or_else(|| anyhow::anyhow!("Cancelled"))
+        .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
         .and_then(|x| x)
     }
 
@@ -3389,8 +3390,10 @@ impl Tenant {
                 );
                 let dest_path =
                     &remote_initdb_archive_path(&self.tenant_shard_id.tenant_id, &timeline_id);
+
+                // if this fails, it will get retried by retried control plane requests
                 storage
-                    .copy_object(source_path, dest_path)
+                    .copy_object(source_path, dest_path, &self.cancel)
                     .await
                     .context("copy initdb tar")?;
             }
@@ -4031,6 +4034,7 @@ pub(crate) mod harness {
             std::fs::create_dir_all(&remote_fs_dir).unwrap();
             let config = RemoteStorageConfig {
                 storage: RemoteStorageKind::LocalFs(remote_fs_dir.clone()),
+                timeout: RemoteStorageConfig::DEFAULT_TIMEOUT,
             };
             let remote_storage = GenericRemoteStorage::from_config(&config).unwrap();
             let deletion_queue = MockDeletionQueue::new(Some(remote_storage.clone()));
diff --git a/pageserver/src/tenant/delete.rs b/pageserver/src/tenant/delete.rs
index 0e192b577c..b64be8dcc5 100644
--- a/pageserver/src/tenant/delete.rs
+++ b/pageserver/src/tenant/delete.rs
@@ -3,7 +3,7 @@ use std::sync::Arc;
 use anyhow::Context;
 use camino::{Utf8Path, Utf8PathBuf};
 use pageserver_api::{models::TenantState, shard::TenantShardId};
-use remote_storage::{GenericRemoteStorage, RemotePath};
+use remote_storage::{GenericRemoteStorage, RemotePath, TimeoutOrCancel};
 use tokio::sync::OwnedMutexGuard;
 use tokio_util::sync::CancellationToken;
 use tracing::{error, instrument, Instrument};
@@ -84,17 +84,17 @@ async fn create_remote_delete_mark(
             let data = bytes::Bytes::from_static(data);
             let stream = futures::stream::once(futures::future::ready(Ok(data)));
             remote_storage
-                .upload(stream, 0, &remote_mark_path, None)
+                .upload(stream, 0, &remote_mark_path, None, cancel)
                 .await
         },
-        |_e| false,
+        TimeoutOrCancel::caused_by_cancel,
         FAILED_UPLOAD_WARN_THRESHOLD,
         FAILED_REMOTE_OP_RETRIES,
         "mark_upload",
         cancel,
     )
     .await
-    .ok_or_else(|| anyhow::anyhow!("Cancelled"))
+    .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
     .and_then(|x| x)
     .context("mark_upload")?;
 
@@ -184,15 +184,15 @@ async fn remove_tenant_remote_delete_mark(
     if let Some(remote_storage) = remote_storage {
         let path = remote_tenant_delete_mark_path(conf, tenant_shard_id)?;
         backoff::retry(
-            || async { remote_storage.delete(&path).await },
-            |_e| false,
+            || async { remote_storage.delete(&path, cancel).await },
+            TimeoutOrCancel::caused_by_cancel,
             FAILED_UPLOAD_WARN_THRESHOLD,
             FAILED_REMOTE_OP_RETRIES,
             "remove_tenant_remote_delete_mark",
             cancel,
         )
         .await
-        .ok_or_else(|| anyhow::anyhow!("Cancelled"))
+        .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
         .and_then(|x| x)
         .context("remove_tenant_remote_delete_mark")?;
     }
diff --git a/pageserver/src/tenant/remote_timeline_client.rs b/pageserver/src/tenant/remote_timeline_client.rs
index 483f53d5c8..91e1179e53 100644
--- a/pageserver/src/tenant/remote_timeline_client.rs
+++ b/pageserver/src/tenant/remote_timeline_client.rs
@@ -196,14 +196,12 @@ pub(crate) use upload::upload_initdb_dir;
 use utils::backoff::{
     self, exponential_backoff, DEFAULT_BASE_BACKOFF_SECONDS, DEFAULT_MAX_BACKOFF_SECONDS,
 };
-use utils::timeout::{timeout_cancellable, TimeoutCancellableError};
 
 use std::collections::{HashMap, VecDeque};
 use std::sync::atomic::{AtomicU32, Ordering};
 use std::sync::{Arc, Mutex};
-use std::time::Duration;
 
-use remote_storage::{DownloadError, GenericRemoteStorage, RemotePath};
+use remote_storage::{DownloadError, GenericRemoteStorage, RemotePath, TimeoutOrCancel};
 use std::ops::DerefMut;
 use tracing::{debug, error, info, instrument, warn};
 use tracing::{info_span, Instrument};
@@ -263,11 +261,6 @@ pub(crate) const INITDB_PRESERVED_PATH: &str = "initdb-preserved.tar.zst";
 /// Default buffer size when interfacing with [`tokio::fs::File`].
 pub(crate) const BUFFER_SIZE: usize = 32 * 1024;
 
-/// This timeout is intended to deal with hangs in lower layers, e.g. stuck TCP flows.  It is not
-/// intended to be snappy enough for prompt shutdown, as we have a CancellationToken for that.
-pub(crate) const UPLOAD_TIMEOUT: Duration = Duration::from_secs(120);
-pub(crate) const DOWNLOAD_TIMEOUT: Duration = Duration::from_secs(120);
-
 pub enum MaybeDeletedIndexPart {
     IndexPart(IndexPart),
     Deleted(IndexPart),
@@ -331,40 +324,6 @@ pub struct RemoteTimelineClient {
     cancel: CancellationToken,
 }
 
-/// Wrapper for timeout_cancellable that flattens result and converts TimeoutCancellableError to anyhow.
-///
-/// This is a convenience for the various upload functions.  In future
-/// the anyhow::Error result should be replaced with a more structured type that
-/// enables callers to avoid handling shutdown as an error.
-async fn upload_cancellable<F>(cancel: &CancellationToken, future: F) -> anyhow::Result<()>
-where
-    F: std::future::Future<Output = anyhow::Result<()>>,
-{
-    match timeout_cancellable(UPLOAD_TIMEOUT, cancel, future).await {
-        Ok(Ok(())) => Ok(()),
-        Ok(Err(e)) => Err(e),
-        Err(TimeoutCancellableError::Timeout) => Err(anyhow::anyhow!("Timeout")),
-        Err(TimeoutCancellableError::Cancelled) => Err(anyhow::anyhow!("Shutting down")),
-    }
-}
-/// Wrapper for timeout_cancellable that flattens result and converts TimeoutCancellableError to DownloaDError.
-async fn download_cancellable<F, R>(
-    cancel: &CancellationToken,
-    future: F,
-) -> Result<R, DownloadError>
-where
-    F: std::future::Future<Output = Result<R, DownloadError>>,
-{
-    match timeout_cancellable(DOWNLOAD_TIMEOUT, cancel, future).await {
-        Ok(Ok(r)) => Ok(r),
-        Ok(Err(e)) => Err(e),
-        Err(TimeoutCancellableError::Timeout) => {
-            Err(DownloadError::Other(anyhow::anyhow!("Timed out")))
-        }
-        Err(TimeoutCancellableError::Cancelled) => Err(DownloadError::Cancelled),
-    }
-}
-
 impl RemoteTimelineClient {
     ///
     /// Create a remote storage client for given timeline
@@ -1050,7 +1009,7 @@ impl RemoteTimelineClient {
             &self.cancel,
         )
         .await
-        .ok_or_else(|| anyhow::anyhow!("Cancelled"))
+        .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
         .and_then(|x| x)?;
 
         // all good, disarm the guard and mark as success
@@ -1082,14 +1041,14 @@ impl RemoteTimelineClient {
                 upload::preserve_initdb_archive(&self.storage_impl, tenant_id, timeline_id, cancel)
                     .await
             },
-            |_e| false,
+            TimeoutOrCancel::caused_by_cancel,
             FAILED_DOWNLOAD_WARN_THRESHOLD,
             FAILED_REMOTE_OP_RETRIES,
             "preserve_initdb_tar_zst",
             &cancel.clone(),
         )
         .await
-        .ok_or_else(|| anyhow::anyhow!("Cancellled"))
+        .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
         .and_then(|x| x)
         .context("backing up initdb archive")?;
         Ok(())
@@ -1151,7 +1110,7 @@ impl RemoteTimelineClient {
         let remaining = download_retry(
             || async {
                 self.storage_impl
-                    .list_files(Some(&timeline_storage_path), None)
+                    .list_files(Some(&timeline_storage_path), None, &cancel)
                     .await
             },
             "list remaining files",
@@ -1445,6 +1404,10 @@ impl RemoteTimelineClient {
                 Ok(()) => {
                     break;
                 }
+                Err(e) if TimeoutOrCancel::caused_by_cancel(&e) => {
+                    // loop around to do the proper stopping
+                    continue;
+                }
                 Err(e) => {
                     let retries = task.retries.fetch_add(1, Ordering::SeqCst);
 
diff --git a/pageserver/src/tenant/remote_timeline_client/download.rs b/pageserver/src/tenant/remote_timeline_client/download.rs
index e755cd08f3..43f5e6c182 100644
--- a/pageserver/src/tenant/remote_timeline_client/download.rs
+++ b/pageserver/src/tenant/remote_timeline_client/download.rs
@@ -11,16 +11,14 @@ use camino::{Utf8Path, Utf8PathBuf};
 use pageserver_api::shard::TenantShardId;
 use tokio::fs::{self, File, OpenOptions};
 use tokio::io::{AsyncSeekExt, AsyncWriteExt};
+use tokio_util::io::StreamReader;
 use tokio_util::sync::CancellationToken;
 use tracing::warn;
-use utils::timeout::timeout_cancellable;
 use utils::{backoff, crashsafe};
 
 use crate::config::PageServerConf;
 use crate::span::debug_assert_current_span_has_tenant_and_timeline_id;
-use crate::tenant::remote_timeline_client::{
-    download_cancellable, remote_layer_path, remote_timelines_path, DOWNLOAD_TIMEOUT,
-};
+use crate::tenant::remote_timeline_client::{remote_layer_path, remote_timelines_path};
 use crate::tenant::storage_layer::LayerFileName;
 use crate::tenant::Generation;
 use crate::virtual_file::on_fatal_io_error;
@@ -83,15 +81,13 @@ pub async fn download_layer_file<'a>(
                 .with_context(|| format!("create a destination file for layer '{temp_file_path}'"))
                 .map_err(DownloadError::Other)?;
 
-            // Cancellation safety: it is safe to cancel this future, because it isn't writing to a local
-            // file: the write to local file doesn't start until after the request header is returned
-            // and we start draining the body stream below
-            let download = download_cancellable(cancel, storage.download(&remote_path))
+            let download = storage
+                .download(&remote_path, cancel)
                 .await
                 .with_context(|| {
                     format!(
-                    "open a download stream for layer with remote storage path '{remote_path:?}'"
-                )
+                        "open a download stream for layer with remote storage path '{remote_path:?}'"
+                    )
                 })
                 .map_err(DownloadError::Other)?;
 
@@ -100,43 +96,26 @@ pub async fn download_layer_file<'a>(
 
             let mut reader = tokio_util::io::StreamReader::new(download.download_stream);
 
-            // Cancellation safety: it is safe to cancel this future because it is writing into a temporary file,
-            // and we will unlink the temporary file if there is an error.  This unlink is important because we
-            // are in a retry loop, and we wouldn't want to leave behind a rogue write I/O to a file that
-            // we will imminiently try and write to again.
-            let bytes_amount: u64 = match timeout_cancellable(
-                DOWNLOAD_TIMEOUT,
-                cancel,
-                tokio::io::copy_buf(&mut reader, &mut destination_file),
-            )
-            .await
-            .with_context(|| {
-                format!(
+            let bytes_amount = tokio::io::copy_buf(&mut reader, &mut destination_file)
+                .await
+                .with_context(|| format!(
                     "download layer at remote path '{remote_path:?}' into file {temp_file_path:?}"
-                )
-            })
-            .map_err(DownloadError::Other)?
-            {
-                Ok(b) => Ok(b),
+                ))
+                .map_err(DownloadError::Other);
+
+            match bytes_amount {
+                Ok(bytes_amount) => {
+                    let destination_file = destination_file.into_inner();
+                    Ok((destination_file, bytes_amount))
+                }
                 Err(e) => {
-                    // Remove incomplete files: on restart Timeline would do this anyway, but we must
-                    // do it here for the retry case.
                     if let Err(e) = tokio::fs::remove_file(&temp_file_path).await {
                         on_fatal_io_error(&e, &format!("Removing temporary file {temp_file_path}"));
                     }
+
                     Err(e)
                 }
             }
-            .with_context(|| {
-                format!(
-                    "download layer at remote path '{remote_path:?}' into file {temp_file_path:?}"
-                )
-            })
-            .map_err(DownloadError::Other)?;
-
-            let destination_file = destination_file.into_inner();
-
-            Ok((destination_file, bytes_amount))
         },
         &format!("download {remote_path:?}"),
         cancel,
@@ -218,9 +197,11 @@ pub async fn list_remote_timelines(
 
     let listing = download_retry_forever(
         || {
-            download_cancellable(
+            storage.list(
+                Some(&remote_path),
+                ListingMode::WithDelimiter,
+                None,
                 &cancel,
-                storage.list(Some(&remote_path), ListingMode::WithDelimiter, None),
             )
         },
         &format!("list timelines for {tenant_shard_id}"),
@@ -259,26 +240,23 @@ async fn do_download_index_part(
     index_generation: Generation,
     cancel: &CancellationToken,
 ) -> Result<IndexPart, DownloadError> {
-    use futures::stream::StreamExt;
-
     let remote_path = remote_index_path(tenant_shard_id, timeline_id, index_generation);
 
     let index_part_bytes = download_retry_forever(
         || async {
-            // Cancellation: if is safe to cancel this future because we're just downloading into
-            // a memory buffer, not touching local disk.
-            let index_part_download =
-                download_cancellable(cancel, storage.download(&remote_path)).await?;
+            let download = storage.download(&remote_path, cancel).await?;
 
-            let mut index_part_bytes = Vec::new();
-            let mut stream = std::pin::pin!(index_part_download.download_stream);
-            while let Some(chunk) = stream.next().await {
-                let chunk = chunk
-                    .with_context(|| format!("download index part at {remote_path:?}"))
-                    .map_err(DownloadError::Other)?;
-                index_part_bytes.extend_from_slice(&chunk[..]);
-            }
-            Ok(index_part_bytes)
+            let mut bytes = Vec::new();
+
+            let stream = download.download_stream;
+            let mut stream = StreamReader::new(stream);
+
+            tokio::io::copy_buf(&mut stream, &mut bytes)
+                .await
+                .with_context(|| format!("download index part at {remote_path:?}"))
+                .map_err(DownloadError::Other)?;
+
+            Ok(bytes)
         },
         &format!("download {remote_path:?}"),
         cancel,
@@ -373,7 +351,7 @@ pub(super) async fn download_index_part(
     let index_prefix = remote_index_path(tenant_shard_id, timeline_id, Generation::none());
 
     let indices = download_retry(
-        || async { storage.list_files(Some(&index_prefix), None).await },
+        || async { storage.list_files(Some(&index_prefix), None, cancel).await },
         "list index_part files",
         cancel,
     )
@@ -446,11 +424,10 @@ pub(crate) async fn download_initdb_tar_zst(
                 .with_context(|| format!("tempfile creation {temp_path}"))
                 .map_err(DownloadError::Other)?;
 
-            let download = match download_cancellable(cancel, storage.download(&remote_path)).await
-            {
+            let download = match storage.download(&remote_path, cancel).await {
                 Ok(dl) => dl,
                 Err(DownloadError::NotFound) => {
-                    download_cancellable(cancel, storage.download(&remote_preserved_path)).await?
+                    storage.download(&remote_preserved_path, cancel).await?
                 }
                 Err(other) => Err(other)?,
             };
@@ -460,6 +437,7 @@ pub(crate) async fn download_initdb_tar_zst(
             // TODO: this consumption of the response body should be subject to timeout + cancellation, but
             // not without thinking carefully about how to recover safely from cancelling a write to
             // local storage (e.g. by writing into a temp file as we do in download_layer)
+            // FIXME: flip the weird error wrapping
             tokio::io::copy_buf(&mut download, &mut writer)
                 .await
                 .with_context(|| format!("download initdb.tar.zst at {remote_path:?}"))
diff --git a/pageserver/src/tenant/remote_timeline_client/upload.rs b/pageserver/src/tenant/remote_timeline_client/upload.rs
index c17e27b446..137fe48b73 100644
--- a/pageserver/src/tenant/remote_timeline_client/upload.rs
+++ b/pageserver/src/tenant/remote_timeline_client/upload.rs
@@ -16,7 +16,7 @@ use crate::{
     config::PageServerConf,
     tenant::remote_timeline_client::{
         index::IndexPart, remote_index_path, remote_initdb_archive_path,
-        remote_initdb_preserved_archive_path, remote_path, upload_cancellable,
+        remote_initdb_preserved_archive_path, remote_path,
     },
 };
 use remote_storage::{GenericRemoteStorage, TimeTravelError};
@@ -49,16 +49,15 @@ pub(crate) async fn upload_index_part<'a>(
     let index_part_bytes = bytes::Bytes::from(index_part_bytes);
 
     let remote_path = remote_index_path(tenant_shard_id, timeline_id, generation);
-    upload_cancellable(
-        cancel,
-        storage.upload_storage_object(
+    storage
+        .upload_storage_object(
             futures::stream::once(futures::future::ready(Ok(index_part_bytes))),
             index_part_size,
             &remote_path,
-        ),
-    )
-    .await
-    .with_context(|| format!("upload index part for '{tenant_shard_id} / {timeline_id}'"))
+            cancel,
+        )
+        .await
+        .with_context(|| format!("upload index part for '{tenant_shard_id} / {timeline_id}'"))
 }
 
 /// Attempts to upload given layer files.
@@ -115,11 +114,10 @@ pub(super) async fn upload_timeline_layer<'a>(
 
     let reader = tokio_util::io::ReaderStream::with_capacity(source_file, super::BUFFER_SIZE);
 
-    upload_cancellable(cancel, storage.upload(reader, fs_size, &storage_path, None))
+    storage
+        .upload(reader, fs_size, &storage_path, None, cancel)
         .await
-        .with_context(|| format!("upload layer from local path '{source_path}'"))?;
-
-    Ok(())
+        .with_context(|| format!("upload layer from local path '{source_path}'"))
 }
 
 /// Uploads the given `initdb` data to the remote storage.
@@ -139,12 +137,10 @@ pub(crate) async fn upload_initdb_dir(
     let file = tokio_util::io::ReaderStream::with_capacity(initdb_tar_zst, super::BUFFER_SIZE);
 
     let remote_path = remote_initdb_archive_path(tenant_id, timeline_id);
-    upload_cancellable(
-        cancel,
-        storage.upload_storage_object(file, size as usize, &remote_path),
-    )
-    .await
-    .with_context(|| format!("upload initdb dir for '{tenant_id} / {timeline_id}'"))
+    storage
+        .upload_storage_object(file, size as usize, &remote_path, cancel)
+        .await
+        .with_context(|| format!("upload initdb dir for '{tenant_id} / {timeline_id}'"))
 }
 
 pub(crate) async fn preserve_initdb_archive(
@@ -155,7 +151,8 @@ pub(crate) async fn preserve_initdb_archive(
 ) -> anyhow::Result<()> {
     let source_path = remote_initdb_archive_path(tenant_id, timeline_id);
     let dest_path = remote_initdb_preserved_archive_path(tenant_id, timeline_id);
-    upload_cancellable(cancel, storage.copy_object(&source_path, &dest_path))
+    storage
+        .copy_object(&source_path, &dest_path, cancel)
         .await
         .with_context(|| format!("backing up initdb archive for '{tenant_id} / {timeline_id}'"))
 }
diff --git a/pageserver/src/tenant/secondary/downloader.rs b/pageserver/src/tenant/secondary/downloader.rs
index c23416a7f0..6966cf7709 100644
--- a/pageserver/src/tenant/secondary/downloader.rs
+++ b/pageserver/src/tenant/secondary/downloader.rs
@@ -523,12 +523,13 @@ impl<'a> TenantDownloader<'a> {
         tracing::debug!("Downloading heatmap for secondary tenant",);
 
         let heatmap_path = remote_heatmap_path(tenant_shard_id);
+        let cancel = &self.secondary_state.cancel;
 
         let heatmap_bytes = backoff::retry(
             || async {
                 let download = self
                     .remote_storage
-                    .download(&heatmap_path)
+                    .download(&heatmap_path, cancel)
                     .await
                     .map_err(UpdateError::from)?;
                 let mut heatmap_bytes = Vec::new();
@@ -540,7 +541,7 @@ impl<'a> TenantDownloader<'a> {
             FAILED_DOWNLOAD_WARN_THRESHOLD,
             FAILED_REMOTE_OP_RETRIES,
             "download heatmap",
-            &self.secondary_state.cancel,
+            cancel,
         )
         .await
         .ok_or_else(|| UpdateError::Cancelled)
diff --git a/pageserver/src/tenant/secondary/heatmap_uploader.rs b/pageserver/src/tenant/secondary/heatmap_uploader.rs
index 806e3fb0e8..660459a733 100644
--- a/pageserver/src/tenant/secondary/heatmap_uploader.rs
+++ b/pageserver/src/tenant/secondary/heatmap_uploader.rs
@@ -21,18 +21,17 @@ use futures::Future;
 use md5;
 use pageserver_api::shard::TenantShardId;
 use rand::Rng;
-use remote_storage::GenericRemoteStorage;
+use remote_storage::{GenericRemoteStorage, TimeoutOrCancel};
 
 use super::{
+    heatmap::HeatMapTenant,
     scheduler::{self, JobGenerator, RunningJob, SchedulingResult, TenantBackgroundJobs},
-    CommandRequest,
+    CommandRequest, UploadCommand,
 };
 use tokio_util::sync::CancellationToken;
 use tracing::{info_span, instrument, Instrument};
 use utils::{backoff, completion::Barrier, yielding_loop::yielding_loop};
 
-use super::{heatmap::HeatMapTenant, UploadCommand};
-
 pub(super) async fn heatmap_uploader_task(
     tenant_manager: Arc<TenantManager>,
     remote_storage: GenericRemoteStorage,
@@ -417,10 +416,10 @@ async fn upload_tenant_heatmap(
         || async {
             let bytes = futures::stream::once(futures::future::ready(Ok(bytes.clone())));
             remote_storage
-                .upload_storage_object(bytes, size, &path)
+                .upload_storage_object(bytes, size, &path, cancel)
                 .await
         },
-        |_| false,
+        TimeoutOrCancel::caused_by_cancel,
         3,
         u32::MAX,
         "Uploading heatmap",
diff --git a/proxy/src/context/parquet.rs b/proxy/src/context/parquet.rs
index ad22829183..d941445c2d 100644
--- a/proxy/src/context/parquet.rs
+++ b/proxy/src/context/parquet.rs
@@ -13,7 +13,7 @@ use parquet::{
     },
     record::RecordWriter,
 };
-use remote_storage::{GenericRemoteStorage, RemotePath, RemoteStorageConfig};
+use remote_storage::{GenericRemoteStorage, RemotePath, RemoteStorageConfig, TimeoutOrCancel};
 use tokio::{sync::mpsc, time};
 use tokio_util::sync::CancellationToken;
 use tracing::{debug, info, Span};
@@ -314,20 +314,23 @@ async fn upload_parquet(
     let path = RemotePath::from_string(&format!(
         "{year:04}/{month:02}/{day:02}/{hour:02}/requests_{id}.parquet"
     ))?;
+    let cancel = CancellationToken::new();
     backoff::retry(
         || async {
             let stream = futures::stream::once(futures::future::ready(Ok(data.clone())));
-            storage.upload(stream, data.len(), &path, None).await
+            storage
+                .upload(stream, data.len(), &path, None, &cancel)
+                .await
         },
-        |_e| false,
+        TimeoutOrCancel::caused_by_cancel,
         FAILED_UPLOAD_WARN_THRESHOLD,
         FAILED_UPLOAD_MAX_RETRIES,
         "request_data_upload",
         // we don't want cancellation to interrupt here, so we make a dummy cancel token
-        &CancellationToken::new(),
+        &cancel,
     )
     .await
-    .ok_or_else(|| anyhow::anyhow!("Cancelled"))
+    .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
     .and_then(|x| x)
     .context("request_data_upload")?;
 
@@ -413,7 +416,8 @@ mod tests {
                     )
                     .unwrap(),
                     max_keys_per_list_response: DEFAULT_MAX_KEYS_PER_LIST_RESPONSE,
-                })
+                }),
+                timeout: RemoteStorageConfig::DEFAULT_TIMEOUT,
             })
         );
         assert_eq!(parquet_upload.parquet_upload_row_group_size, 100);
@@ -466,6 +470,7 @@ mod tests {
     ) -> Vec<(u64, usize, i64)> {
         let remote_storage_config = RemoteStorageConfig {
             storage: RemoteStorageKind::LocalFs(tmpdir.to_path_buf()),
+            timeout: std::time::Duration::from_secs(120),
         };
         let storage = GenericRemoteStorage::from_config(&remote_storage_config).unwrap();
 
diff --git a/safekeeper/src/wal_backup.rs b/safekeeper/src/wal_backup.rs
index dbdc742d26..944d80f777 100644
--- a/safekeeper/src/wal_backup.rs
+++ b/safekeeper/src/wal_backup.rs
@@ -511,7 +511,11 @@ async fn backup_object(
 
     let file = tokio_util::io::ReaderStream::with_capacity(file, BUFFER_SIZE);
 
-    storage.upload_storage_object(file, size, target_file).await
+    let cancel = CancellationToken::new();
+
+    storage
+        .upload_storage_object(file, size, target_file, &cancel)
+        .await
 }
 
 pub async fn read_object(
@@ -526,8 +530,10 @@ pub async fn read_object(
 
     info!("segment download about to start from remote path {file_path:?} at offset {offset}");
 
+    let cancel = CancellationToken::new();
+
     let download = storage
-        .download_storage_object(Some((offset, None)), file_path)
+        .download_storage_object(Some((offset, None)), file_path, &cancel)
         .await
         .with_context(|| {
             format!("Failed to open WAL segment download stream for remote path {file_path:?}")
@@ -559,7 +565,8 @@ pub async fn delete_timeline(ttid: &TenantTimelineId) -> Result<()> {
     // Note: listing segments might take a long time if there are many of them.
     // We don't currently have http requests timeout cancellation, but if/once
     // we have listing should get streaming interface to make progress.
-    let token = CancellationToken::new(); // not really used
+
+    let cancel = CancellationToken::new(); // not really used
     backoff::retry(
         || async {
             // Do list-delete in batch_size batches to make progress even if there a lot of files.
@@ -567,7 +574,7 @@ pub async fn delete_timeline(ttid: &TenantTimelineId) -> Result<()> {
             // I'm not sure deleting while iterating is expected in s3.
             loop {
                 let files = storage
-                    .list_files(Some(&remote_path), Some(batch_size))
+                    .list_files(Some(&remote_path), Some(batch_size), &cancel)
                     .await?;
                 if files.is_empty() {
                     return Ok(()); // done
@@ -580,14 +587,15 @@ pub async fn delete_timeline(ttid: &TenantTimelineId) -> Result<()> {
                     files.first().unwrap().object_name().unwrap_or(""),
                     files.last().unwrap().object_name().unwrap_or("")
                 );
-                storage.delete_objects(&files).await?;
+                storage.delete_objects(&files, &cancel).await?;
             }
         },
+        // consider TimeoutOrCancel::caused_by_cancel when using cancellation
         |_| false,
         3,
         10,
         "executing WAL segments deletion batch",
-        &token,
+        &cancel,
     )
     .await
     .ok_or_else(|| anyhow::anyhow!("canceled"))
@@ -617,7 +625,12 @@ pub async fn copy_s3_segments(
 
     let remote_path = RemotePath::new(&relative_dst_path)?;
 
-    let files = storage.list_files(Some(&remote_path), None).await?;
+    let cancel = CancellationToken::new();
+
+    let files = storage
+        .list_files(Some(&remote_path), None, &cancel)
+        .await?;
+
     let uploaded_segments = &files
         .iter()
         .filter_map(|file| file.object_name().map(ToOwned::to_owned))
@@ -645,7 +658,7 @@ pub async fn copy_s3_segments(
         let from = RemotePath::new(&relative_src_path.join(&segment_name))?;
         let to = RemotePath::new(&relative_dst_path.join(&segment_name))?;
 
-        storage.copy_object(&from, &to).await?;
+        storage.copy_object(&from, &to, &cancel).await?;
     }
 
     info!(