diff --git a/test_runner/regress/test_remote_storage.py b/test_runner/regress/test_remote_storage.py
index 90ebb887b3..1b40e9b1c3 100644
--- a/test_runner/regress/test_remote_storage.py
+++ b/test_runner/regress/test_remote_storage.py
@@ -243,20 +243,6 @@ def test_remote_storage_upload_queue_retries(
         )
         wait_for_last_flush_lsn(env, pg, tenant_id, timeline_id)
 
-    # let all of them queue up
-    configure_storage_sync_failpoints("return")
-
-    overwrite_data_and_wait_for_it_to_arrive_at_pageserver("a")
-    client.timeline_checkpoint(tenant_id, timeline_id)
-    # now overwrite it again
-    overwrite_data_and_wait_for_it_to_arrive_at_pageserver("b")
-    # trigger layer deletion by doing Compaction, then GC
-    client.timeline_compact(tenant_id, timeline_id)
-    gc_result = client.timeline_gc(tenant_id, timeline_id, 0)
-    print_gc_result(gc_result)
-    assert gc_result["layers_removed"] > 0
-
-    # confirm all operations are queued up
     def get_queued_count(file_kind, op_kind):
         metrics = client.get_metrics()
         matches = re.search(
@@ -267,14 +253,43 @@ def test_remote_storage_upload_queue_retries(
         assert matches
         return int(matches[1])
 
+    # create some layers & wait for uploads to finish
+    overwrite_data_and_wait_for_it_to_arrive_at_pageserver("a")
+    client.timeline_checkpoint(tenant_id, timeline_id)
+    overwrite_data_and_wait_for_it_to_arrive_at_pageserver("b")
+    client.timeline_checkpoint(tenant_id, timeline_id)
+    client.timeline_compact(tenant_id, timeline_id)
+    gc_result = client.timeline_gc(tenant_id, timeline_id, 0)
+    print_gc_result(gc_result)
+    assert gc_result["layers_removed"] > 0
+
+    wait_until(2, 1, lambda: get_queued_count(file_kind="layer", op_kind="upload") == 0)
+    wait_until(2, 1, lambda: get_queued_count(file_kind="index", op_kind="upload") == 0)
+    wait_until(2, 1, lambda: get_queued_count(file_kind="layer", op_kind="delete") == 0)
+
+    # let all future operations queue up
+    configure_storage_sync_failpoints("return")
+
+    # create more churn to generate all upload ops
+    overwrite_data_and_wait_for_it_to_arrive_at_pageserver("c")
+    client.timeline_checkpoint(tenant_id, timeline_id)
+    overwrite_data_and_wait_for_it_to_arrive_at_pageserver("d")
+    client.timeline_compact(tenant_id, timeline_id)
+    gc_result = client.timeline_gc(tenant_id, timeline_id, 0)
+    print_gc_result(gc_result)
+    assert gc_result["layers_removed"] > 0
+
     # ensure that all operation types that can be in the upload queue have queued up
     assert get_queued_count(file_kind="layer", op_kind="upload") > 0
     assert get_queued_count(file_kind="index", op_kind="upload") >= 2
-    assert get_queued_count(file_kind="layer", op_kind="remove") > 0
+    assert get_queued_count(file_kind="layer", op_kind="delete") > 0
 
     # unblock all operations and wait for them to finish
     configure_storage_sync_failpoints("off")
-    wait_until(10, 1, lambda: get_queued_count() == 0)
+
+    wait_until(30, 1, lambda: get_queued_count(file_kind="layer", op_kind="upload") == 0)
+    wait_until(30, 1, lambda: get_queued_count(file_kind="index", op_kind="upload") == 0)
+    wait_until(30, 1, lambda: get_queued_count(file_kind="layer", op_kind="delete") == 0)
 
     # try a restore to verify that the uploads worked
     # XXX: should vary this test to selectively fail just layer uploads, index uploads, deletions
@@ -303,4 +318,4 @@ def test_remote_storage_upload_queue_retries(
     log.info("restarting postgres to validate")
     pg = env.postgres.create_start("main", tenant_id=tenant_id)
     with pg.cursor() as cur:
-        assert query_scalar(cur, "SELECT COUNT(*) FROM foo WHERE val = 'b'") == 10000
+        assert query_scalar(cur, "SELECT COUNT(*) FROM foo WHERE val = 'd'") == 10000