diff --git a/pageserver/src/http/routes.rs b/pageserver/src/http/routes.rs
index d57bd98e95..dde9c5dd0b 100644
--- a/pageserver/src/http/routes.rs
+++ b/pageserver/src/http/routes.rs
@@ -2002,9 +2002,9 @@ async fn timeline_offload_handler(
                 "timeline has attached children".into(),
             ));
         }
-        if !timeline.can_offload() {
+        if let (false, reason) = timeline.can_offload() {
             return Err(ApiError::PreconditionFailed(
-                "Timeline::can_offload() returned false".into(),
+                format!("Timeline::can_offload() check failed: {}", reason) .into(),
             ));
         }
         offload_timeline(&tenant, &timeline)
diff --git a/pageserver/src/tenant.rs b/pageserver/src/tenant.rs
index 34ea6dae1f..903174680e 100644
--- a/pageserver/src/tenant.rs
+++ b/pageserver/src/tenant.rs
@@ -2493,7 +2493,8 @@ impl Tenant {
             timelines_to_compact_or_offload = timelines
                 .iter()
                 .filter_map(|(timeline_id, timeline)| {
-                    let (is_active, can_offload) = (timeline.is_active(), timeline.can_offload());
+                    let (is_active, (can_offload, _)) =
+                        (timeline.is_active(), timeline.can_offload());
                     let has_no_unoffloaded_children = {
                         !timelines
                             .iter()
diff --git a/pageserver/src/tenant/timeline.rs b/pageserver/src/tenant/timeline.rs
index 60cc689c5e..56faacbaee 100644
--- a/pageserver/src/tenant/timeline.rs
+++ b/pageserver/src/tenant/timeline.rs
@@ -1570,12 +1570,16 @@ impl Timeline {
     ///
     /// This is neccessary but not sufficient for offloading of the timeline as it might have
     /// child timelines that are not offloaded yet.
-    pub(crate) fn can_offload(&self) -> bool {
+    pub(crate) fn can_offload(&self) -> (bool, &'static str) {
         if self.remote_client.is_archived() != Some(true) {
-            return false;
+            return (false, "the timeline is not archived");
+        }
+        if !self.remote_client.no_pending_work() {
+            // if the remote client is still processing some work, we can't offload
+            return (false, "the upload queue is not drained yet");
         }
 
-        true
+        (true, "ok")
     }
 
     /// Outermost timeline compaction operation; downloads needed layers. Returns whether we have pending
diff --git a/pageserver/src/tenant/timeline/offload.rs b/pageserver/src/tenant/timeline/offload.rs
index 2dc461c28d..1394843467 100644
--- a/pageserver/src/tenant/timeline/offload.rs
+++ b/pageserver/src/tenant/timeline/offload.rs
@@ -58,7 +58,7 @@ pub(crate) async fn offload_timeline(
     }
 
     // Now that the Timeline is in Stopping state, request all the related tasks to shut down.
-    timeline.shutdown(super::ShutdownMode::Hard).await;
+    timeline.shutdown(super::ShutdownMode::Flush).await;
 
     // TODO extend guard mechanism above with method
     // to make deletions possible while offloading is in progress