diff --git a/pageserver/src/storage_sync.rs b/pageserver/src/storage_sync.rs
index 0e2580de85..86c3f9b6af 100644
--- a/pageserver/src/storage_sync.rs
+++ b/pageserver/src/storage_sync.rs
@@ -684,38 +684,53 @@ impl RemoteTimelineClient {
         let mut guard = self.upload_queue.lock().unwrap();
         let upload_queue = guard.initialized_mut()?;
 
-        // Update the remote index file, removing the to-be-deleted files from the index,
-        // before deleting the actual files.
-        // NB: deleting layers doesn't affect the values stored in TimelineMetadata,
-        //     so, we don't need update it.
-
+        // Convert the paths into RelativePaths, and gather other information we need.
+        let mut relative_paths = Vec::with_capacity(paths.len());
         for path in paths {
-            let relative_path = RelativePath::from_local_path(
+            relative_paths.push(RelativePath::from_local_path(
                 &self.conf.timeline_path(&self.timeline_id, &self.tenant_id),
                 path,
-            )?;
-            upload_queue.latest_files.remove(&relative_path);
+            )?);
         }
-        let disk_consistent_lsn = upload_queue.latest_metadata.disk_consistent_lsn();
-        let index_part = IndexPart::new(
-            upload_queue.latest_files.clone(),
-            disk_consistent_lsn,
-            upload_queue.latest_metadata.to_bytes()?,
-        );
-        let op = UploadOp::UploadMetadata(index_part, disk_consistent_lsn);
-        self.update_upload_queue_unfinished_metric(1, &op);
-        upload_queue.queued_operations.push_back(op);
 
-        // schedule the actual deletions
-        for path in paths {
-            let op = UploadOp::Delete(RemoteOpFileKind::Layer, PathBuf::from(path));
+        // Deleting layers doesn't affect the values stored in TimelineMetadata,
+        // so we don't need update it. Just serialize it.
+        let metadata_bytes = upload_queue.latest_metadata.to_bytes()?;
+        let disk_consistent_lsn = upload_queue.latest_metadata.disk_consistent_lsn();
+
+        // Update the remote index file, removing the to-be-deleted files from the index,
+        // before deleting the actual files.
+        //
+        // Once we start removing files from upload_queue.latest_files, there's
+        // no going back! Otherwise, some of the files would already be removed
+        // from latest_files, but not yet scheduled for deletion. Use a closure
+        // to syntactically forbid ? or bail! calls here.
+        let no_bail_here = || {
+            for relative_path in relative_paths {
+                upload_queue.latest_files.remove(&relative_path);
+            }
+
+            let index_part = IndexPart::new(
+                upload_queue.latest_files.clone(),
+                disk_consistent_lsn,
+                metadata_bytes,
+            );
+            let op = UploadOp::UploadMetadata(index_part, disk_consistent_lsn);
             self.update_upload_queue_unfinished_metric(1, &op);
             upload_queue.queued_operations.push_back(op);
-            info!("scheduled layer file deletion {}", path.display());
-        }
 
-        // Launch the tasks immediately, if possible
-        self.launch_queued_tasks(upload_queue);
+            // schedule the actual deletions
+            for path in paths {
+                let op = UploadOp::Delete(RemoteOpFileKind::Layer, PathBuf::from(path));
+                self.update_upload_queue_unfinished_metric(1, &op);
+                upload_queue.queued_operations.push_back(op);
+                info!("scheduled layer file deletion {}", path.display());
+            }
+
+            // Launch the tasks immediately, if possible
+            self.launch_queued_tasks(upload_queue);
+        };
+        no_bail_here();
         Ok(())
     }
 
diff --git a/test_runner/regress/test_tenants_with_remote_storage.py b/test_runner/regress/test_tenants_with_remote_storage.py
index 1a1f9da41e..1318720973 100644
--- a/test_runner/regress/test_tenants_with_remote_storage.py
+++ b/test_runner/regress/test_tenants_with_remote_storage.py
@@ -164,7 +164,10 @@ def test_tenants_attached_after_download(
     detail_before = client.timeline_detail(
         tenant_id, timeline_id, include_non_incremental_physical_size=True
     )
-    assert detail_before["current_physical_size_non_incremental"] == detail_before["current_physical_size"]
+    assert (
+        detail_before["current_physical_size_non_incremental"]
+        == detail_before["current_physical_size"]
+    )
 
     env.pageserver.stop()