diff --git a/libs/remote_storage/src/s3_bucket.rs b/libs/remote_storage/src/s3_bucket.rs
index 38e1bf00f8..dafb6dcb45 100644
--- a/libs/remote_storage/src/s3_bucket.rs
+++ b/libs/remote_storage/src/s3_bucket.rs
@@ -34,6 +34,8 @@ use crate::{
     Download, DownloadError, RemotePath, RemoteStorage, S3Config, REMOTE_STORAGE_PREFIX_SEPARATOR,
 };
 
+const MAX_DELETE_OBJECTS_REQUEST_SIZE: usize = 1000;
+
 pub(super) mod metrics {
     use metrics::{register_int_counter_vec, IntCounterVec};
     use once_cell::sync::Lazy;
@@ -424,17 +426,33 @@ impl RemoteStorage for S3Bucket {
             delete_objects.push(obj_id);
         }
 
-        metrics::inc_delete_objects(paths.len() as u64);
-        self.client
-            .delete_objects()
-            .bucket(self.bucket_name.clone())
-            .delete(Delete::builder().set_objects(Some(delete_objects)).build())
-            .send()
-            .await
-            .map_err(|e| {
-                metrics::inc_delete_objects_fail(paths.len() as u64);
-                e
-            })?;
+        for chunk in delete_objects.chunks(MAX_DELETE_OBJECTS_REQUEST_SIZE) {
+            metrics::inc_delete_objects(chunk.len() as u64);
+
+            let resp = self
+                .client
+                .delete_objects()
+                .bucket(self.bucket_name.clone())
+                .delete(Delete::builder().set_objects(Some(chunk.to_vec())).build())
+                .send()
+                .await;
+
+            match resp {
+                Ok(resp) => {
+                    if let Some(errors) = resp.errors {
+                        metrics::inc_delete_objects_fail(errors.len() as u64);
+                        return Err(anyhow::format_err!(
+                            "Failed to delete {} objects",
+                            errors.len()
+                        ));
+                    }
+                }
+                Err(e) => {
+                    metrics::inc_delete_objects_fail(chunk.len() as u64);
+                    return Err(e.into());
+                }
+            }
+        }
         Ok(())
     }
 
diff --git a/libs/remote_storage/src/simulate_failures.rs b/libs/remote_storage/src/simulate_failures.rs
index 2f341bb29d..741c18bf6f 100644
--- a/libs/remote_storage/src/simulate_failures.rs
+++ b/libs/remote_storage/src/simulate_failures.rs
@@ -24,6 +24,7 @@ enum RemoteOp {
     Upload(RemotePath),
     Download(RemotePath),
     Delete(RemotePath),
+    DeleteObjects(Vec<RemotePath>),
 }
 
 impl UnreliableWrapper {
@@ -121,8 +122,18 @@ impl RemoteStorage for UnreliableWrapper {
     }
 
     async fn delete_objects<'a>(&self, paths: &'a [RemotePath]) -> anyhow::Result<()> {
+        self.attempt(RemoteOp::DeleteObjects(paths.to_vec()))?;
+        let mut error_counter = 0;
         for path in paths {
-            self.delete(path).await?
+            if (self.delete(path).await).is_err() {
+                error_counter += 1;
+            }
+        }
+        if error_counter > 0 {
+            return Err(anyhow::anyhow!(
+                "failed to delete {} objects",
+                error_counter
+            ));
         }
         Ok(())
     }