diff --git a/acceptance/bundle/deploy/files/out-of-band-delete/databricks.yml b/acceptance/bundle/deploy/files/out-of-band-delete/databricks.yml
new file mode 100644
index 00000000000..a4c66846c58
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/databricks.yml
@@ -0,0 +1,15 @@
+bundle:
+  name: out-of-band-delete
+
+resources:
+  jobs:
+    foo:
+      name: test-job
+      tasks:
+        - task_key: my_task
+          spark_python_task:
+            python_file: ./hello_world.py
+          new_cluster:
+            num_workers: 1
+            spark_version: 13.3.x-snapshot-scala2.12
+            node_type_id: i3.xlarge
diff --git a/acceptance/bundle/deploy/files/out-of-band-delete/hello_world.py b/acceptance/bundle/deploy/files/out-of-band-delete/hello_world.py
new file mode 100644
index 00000000000..f301245e242
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/hello_world.py
@@ -0,0 +1 @@
+print("Hello World!")
diff --git a/acceptance/bundle/deploy/files/out-of-band-delete/out.test.toml b/acceptance/bundle/deploy/files/out-of-band-delete/out.test.toml
new file mode 100644
index 00000000000..f784a183258
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/out.test.toml
@@ -0,0 +1,3 @@
+Local = true
+Cloud = false
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["terraform", "direct"]
diff --git a/acceptance/bundle/deploy/files/out-of-band-delete/output.txt b/acceptance/bundle/deploy/files/out-of-band-delete/output.txt
new file mode 100644
index 00000000000..c46bbfb2f89
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/output.txt
@@ -0,0 +1,47 @@
+
+>>> [CLI] bundle deploy
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files...
+Deploying resources...
+Updating deployment state...
+Deployment complete!
+
+=== After the initial deploy the job's python_file and the deployment state exist
+>>> [CLI] workspace get-status /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files/hello_world.py
+{
+  "object_type": "FILE",
+  "path": "/Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files/hello_world.py"
+}
+
+>>> [CLI] workspace get-status /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/state/deployment.json
+{
+  "object_type": "FILE",
+  "path": "/Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/state/deployment.json"
+}
+
+=== Delete the remote bundle directory out-of-band (simulates deleting it in the UI)
+>>> [CLI] workspace delete --recursive /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete
+
+=== Redeploy without changing any local file, so the stale sync snapshot is reused
+>>> [CLI] bundle deploy
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files...
+Deploying resources...
+Updating deployment state...
+Deployment complete!
+
+=== After redeploy: the files dir and state are recreated, but the python_file is NOT re-uploaded
+>>> errcode [CLI] workspace get-status /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files/hello_world.py
+Error: Workspace path not found
+
+Exit code: 1
+
+>>> [CLI] workspace get-status /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files
+{
+  "object_type": "DIRECTORY",
+  "path": "/Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files"
+}
+
+>>> [CLI] workspace get-status /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/state/deployment.json
+{
+  "object_type": "FILE",
+  "path": "/Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/state/deployment.json"
+}
diff --git a/acceptance/bundle/deploy/files/out-of-band-delete/script b/acceptance/bundle/deploy/files/out-of-band-delete/script
new file mode 100644
index 00000000000..46b95a26528
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/script
@@ -0,0 +1,31 @@
+# Redeploy after the remote bundle directory is deleted out-of-band (e.g. a user
+# deletes it in the workspace UI).
+#
+# After such a deletion the next "bundle deploy" does not re-upload the bundle files:
+# the local sync snapshot still records them as present remotely, and the remote
+# deployment state that would otherwise reset the snapshot was deleted too, so the
+# file sync computes an empty diff and uploads nothing.
+#
+# This test pins down the current behaviour: hello_world.py is missing from the
+# workspace after the redeploy even though the deploy reports success. If the file
+# sync is changed to re-upload in this case, the final get-status will succeed and
+# this output is expected to change.
+
+BUNDLE_PATH="/Workspace/Users/${CURRENT_USER_NAME}/.bundle/out-of-band-delete/default"
+
+trace $CLI bundle deploy
+
+title "After the initial deploy the job's python_file and the deployment state exist"
+trace $CLI workspace get-status "$BUNDLE_PATH/files/hello_world.py" | jq '{object_type,path}'
+trace $CLI workspace get-status "$BUNDLE_PATH/state/deployment.json" | jq '{object_type,path}'
+
+title "Delete the remote bundle directory out-of-band (simulates deleting it in the UI)"
+trace $CLI workspace delete --recursive "/Workspace/Users/${CURRENT_USER_NAME}/.bundle/out-of-band-delete"
+
+title "Redeploy without changing any local file, so the stale sync snapshot is reused"
+trace $CLI bundle deploy
+
+title "After redeploy: the files dir and state are recreated, but the python_file is NOT re-uploaded"
+trace errcode $CLI workspace get-status "$BUNDLE_PATH/files/hello_world.py"
+trace $CLI workspace get-status "$BUNDLE_PATH/files" | jq '{object_type,path}'
+trace $CLI workspace get-status "$BUNDLE_PATH/state/deployment.json" | jq '{object_type,path}'