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..8ac61e622b7
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/output.txt
@@ -0,0 +1,41 @@
+
+>>> [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 python_file exists
+>>> [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"
+}
+
+=== 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 reuses the stale snapshot, so the python_file is NOT re-uploaded
+>>> [CLI] bundle deploy
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files...
+Deploying resources...
+Updating deployment state...
+Deployment complete!
+
+>>> musterr [CLI] workspace get-status /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files/hello_world.py
+Error: Workspace path not found
+
+=== Removing the sync snapshot forces a full re-upload, restoring the python_file
+>>> rm -rf .databricks/bundle/default/sync-snapshots
+
+>>> [CLI] bundle deploy
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/out-of-band-delete/default/files...
+Deploying resources...
+Updating deployment state...
+Deployment complete!
+
+>>> [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"
+}
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..183e58d04a2
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/script
@@ -0,0 +1,21 @@
+# Reproduces https://github.com/databricks/cli/issues/1976: after the remote bundle
+# files are deleted out-of-band, a plain redeploy does not re-upload them.
+
+BUNDLE_PATH="/Workspace/Users/${CURRENT_USER_NAME}/.bundle/out-of-band-delete/default"
+
+trace $CLI bundle deploy
+
+title "After the initial deploy the python_file exists"
+trace $CLI workspace get-status "$BUNDLE_PATH/files/hello_world.py" | 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 reuses the stale snapshot, so the python_file is NOT re-uploaded"
+trace $CLI bundle deploy
+trace musterr $CLI workspace get-status "$BUNDLE_PATH/files/hello_world.py"
+
+title "Removing the sync snapshot forces a full re-upload, restoring the python_file"
+trace rm -rf .databricks/bundle/default/sync-snapshots
+trace $CLI bundle deploy
+trace $CLI workspace get-status "$BUNDLE_PATH/files/hello_world.py" | jq '{object_type,path}'
diff --git a/acceptance/bundle/deploy/files/out-of-band-delete/test.toml b/acceptance/bundle/deploy/files/out-of-band-delete/test.toml
new file mode 100644
index 00000000000..6a62c44e94d
--- /dev/null
+++ b/acceptance/bundle/deploy/files/out-of-band-delete/test.toml
@@ -0,0 +1,9 @@
+Badness = "After the remote bundle files are deleted out-of-band, the next deploy does not re-upload them until the local sync snapshot is removed."
+
+[Env]
+# This test passes absolute workspace paths like /Workspace/Users/.../hello_world.py
+# as CLI arguments. On Windows the script runs under MSYS2, which rewrites such
+# leading-slash arguments to Windows paths (e.g. C:/Program Files/Git/Workspace/...)
+# before the CLI sees them, so workspace get-status would query the wrong path.
+# Setting this environment variable disables that conversion.
+MSYS_NO_PATHCONV = "1"