diff --git a/test_runner/fixtures/neon_fixtures.py b/test_runner/fixtures/neon_fixtures.py
index 195b788c7e..dae440b18d 100644
--- a/test_runner/fixtures/neon_fixtures.py
+++ b/test_runner/fixtures/neon_fixtures.py
@@ -4985,6 +4985,7 @@ def generate_uploads_and_deletions(
     timeline_id: TimelineId | None = None,
     data: str | None = None,
     pageserver: NeonPageserver,
+    wait_for_upload: bool = True,
 ):
     """
     Using the environment's default tenant + timeline, generate a load pattern
@@ -5046,4 +5047,4 @@ def generate_uploads_and_deletions(
         # background ingest, no more uploads pending, and therefore no non-determinism
         # in subsequent actions like pageserver restarts.
         flush_ep_to_pageserver(env, endpoint, tenant_id, timeline_id, pageserver.id)
-        ps_http.timeline_checkpoint(tenant_id, timeline_id, wait_until_uploaded=True)
+        ps_http.timeline_checkpoint(tenant_id, timeline_id, wait_until_uploaded=wait_for_upload)
diff --git a/test_runner/fixtures/pageserver/http.py b/test_runner/fixtures/pageserver/http.py
index a62f6e7b7f..4df624def3 100644
--- a/test_runner/fixtures/pageserver/http.py
+++ b/test_runner/fixtures/pageserver/http.py
@@ -343,7 +343,7 @@ class PageserverHttpClient(requests.Session, MetricsGetter):
         assert isinstance(res_json["tenant_shards"], list)
         return res_json
 
-    def tenant_get_location(self, tenant_id: Union[TenantId, TenantShardId]):
+    def tenant_get_location(self, tenant_id: TenantId | TenantShardId):
         res = self.get(
             f"http://localhost:{self.port}/v1/location_config/{tenant_id}",
         )
diff --git a/test_runner/regress/test_pageserver_generations.py b/test_runner/regress/test_pageserver_generations.py
index d5bbfbc7fc..bc15b48645 100644
--- a/test_runner/regress/test_pageserver_generations.py
+++ b/test_runner/regress/test_pageserver_generations.py
@@ -459,7 +459,11 @@ def test_emergency_mode(neon_env_builder: NeonEnvBuilder, pg_bin: PgBin):
     env.pageserver.start()
 
     # The pageserver should provide service to clients
-    generate_uploads_and_deletions(env, init=False, pageserver=env.pageserver)
+    # Because it is in emergency mode, it will not attempt to validate deletions required by the initial barrier, and therefore
+    # other files cannot be uploaded b/c it's waiting for the initial barrier to be validated.
+    generate_uploads_and_deletions(
+        env, init=False, pageserver=env.pageserver, wait_for_upload=False
+    )
 
     # The pageserver should neither validate nor execute any deletions, it should have
     # loaded the DeletionLists from before though