diff --git a/pageserver/src/tenant/tasks.rs b/pageserver/src/tenant/tasks.rs
index 2b2fcc7711..5f39c46a84 100644
--- a/pageserver/src/tenant/tasks.rs
+++ b/pageserver/src/tenant/tasks.rs
@@ -9,6 +9,7 @@ use crate::context::{DownloadBehavior, RequestContext};
 use crate::metrics::TENANT_TASK_EVENTS;
 use crate::task_mgr;
 use crate::task_mgr::{TaskKind, BACKGROUND_RUNTIME};
+use crate::tenant::timeline::CompactionError;
 use crate::tenant::{Tenant, TenantState};
 use tokio_util::sync::CancellationToken;
 use tracing::*;
@@ -181,8 +182,11 @@ async fn compaction_loop(tenant: Arc<Tenant>, cancel: CancellationToken) {
                     );
                     error_run_count += 1;
                     let wait_duration = Duration::from_secs_f64(wait_duration);
-                    error!(
-                        "Compaction failed {error_run_count} times, retrying in {wait_duration:?}: {e:?}",
+                    log_compaction_error(
+                        &e,
+                        error_run_count,
+                        &wait_duration,
+                        cancel.is_cancelled(),
                     );
                     wait_duration
                 } else {
@@ -210,6 +214,58 @@ async fn compaction_loop(tenant: Arc<Tenant>, cancel: CancellationToken) {
     TENANT_TASK_EVENTS.with_label_values(&["stop"]).inc();
 }
 
+fn log_compaction_error(
+    e: &CompactionError,
+    error_run_count: u32,
+    sleep_duration: &std::time::Duration,
+    task_cancelled: bool,
+) {
+    use crate::tenant::upload_queue::NotInitialized;
+    use crate::tenant::PageReconstructError;
+    use CompactionError::*;
+
+    enum LooksLike {
+        Info,
+        Error,
+    }
+
+    let decision = match e {
+        ShuttingDown => None,
+        _ if task_cancelled => Some(LooksLike::Info),
+        Other(e) => {
+            let root_cause = e.root_cause();
+
+            let is_stopping = {
+                let upload_queue = root_cause
+                    .downcast_ref::<NotInitialized>()
+                    .is_some_and(|e| e.is_stopping());
+
+                let timeline = root_cause
+                    .downcast_ref::<PageReconstructError>()
+                    .is_some_and(|e| e.is_stopping());
+
+                upload_queue || timeline
+            };
+
+            if is_stopping {
+                Some(LooksLike::Info)
+            } else {
+                Some(LooksLike::Error)
+            }
+        }
+    };
+
+    match decision {
+        Some(LooksLike::Info) => info!(
+            "Compaction failed {error_run_count} times, retrying in {sleep_duration:?}: {e:#}",
+        ),
+        Some(LooksLike::Error) => error!(
+            "Compaction failed {error_run_count} times, retrying in {sleep_duration:?}: {e:?}",
+        ),
+        None => {}
+    }
+}
+
 ///
 /// GC task's main loop
 ///
diff --git a/pageserver/src/tenant/timeline.rs b/pageserver/src/tenant/timeline.rs
index 666dae94e2..c21fe94d01 100644
--- a/pageserver/src/tenant/timeline.rs
+++ b/pageserver/src/tenant/timeline.rs
@@ -392,8 +392,7 @@ pub(crate) enum PageReconstructError {
     #[error("Ancestor LSN wait error: {0}")]
     AncestorLsnTimeout(#[from] WaitLsnError),
 
-    /// The operation was cancelled
-    #[error("Cancelled")]
+    #[error("timeline shutting down")]
     Cancelled,
 
     /// The ancestor of this is being stopped
@@ -405,6 +404,19 @@ pub(crate) enum PageReconstructError {
     WalRedo(anyhow::Error),
 }
 
+impl PageReconstructError {
+    /// Returns true if this error indicates a tenant/timeline shutdown alike situation
+    pub(crate) fn is_stopping(&self) -> bool {
+        use PageReconstructError::*;
+        match self {
+            Other(_) => false,
+            AncestorLsnTimeout(_) => false,
+            Cancelled | AncestorStopping(_) => true,
+            WalRedo(_) => false,
+        }
+    }
+}
+
 #[derive(thiserror::Error, Debug)]
 enum CreateImageLayersError {
     #[error("timeline shutting down")]
diff --git a/pageserver/src/tenant/upload_queue.rs b/pageserver/src/tenant/upload_queue.rs
index 32f14f40c5..0b61bc0a10 100644
--- a/pageserver/src/tenant/upload_queue.rs
+++ b/pageserver/src/tenant/upload_queue.rs
@@ -126,6 +126,27 @@ pub(super) struct UploadQueueStopped {
     pub(super) deleted_at: SetDeletedFlagProgress,
 }
 
+#[derive(thiserror::Error, Debug)]
+pub(crate) enum NotInitialized {
+    #[error("queue is in state Uninitialized")]
+    Uninitialized,
+    #[error("queue is in state Stopping")]
+    Stopped,
+    #[error("queue is shutting down")]
+    ShuttingDown,
+}
+
+impl NotInitialized {
+    pub(crate) fn is_stopping(&self) -> bool {
+        use NotInitialized::*;
+        match self {
+            Uninitialized => false,
+            Stopped => true,
+            ShuttingDown => true,
+        }
+    }
+}
+
 impl UploadQueue {
     pub(crate) fn initialize_empty_remote(
         &mut self,
@@ -214,17 +235,17 @@ impl UploadQueue {
     }
 
     pub(crate) fn initialized_mut(&mut self) -> anyhow::Result<&mut UploadQueueInitialized> {
+        use UploadQueue::*;
         match self {
-            UploadQueue::Uninitialized | UploadQueue::Stopped(_) => {
-                anyhow::bail!("queue is in state {}", self.as_str())
-            }
-            UploadQueue::Initialized(x) => {
-                if !x.shutting_down {
-                    Ok(x)
+            Uninitialized => Err(NotInitialized::Uninitialized.into()),
+            Initialized(x) => {
+                if x.shutting_down {
+                    Err(NotInitialized::ShuttingDown.into())
                 } else {
-                    anyhow::bail!("queue is shutting down")
+                    Ok(x)
                 }
             }
+            Stopped(_) => Err(NotInitialized::Stopped.into()),
         }
     }