diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/databricks.yml b/acceptance/bundle/deploy/readplan/whl-not-uploaded/databricks.yml
new file mode 100644
index 00000000000..f67f45222fb
--- /dev/null
+++ b/acceptance/bundle/deploy/readplan/whl-not-uploaded/databricks.yml
@@ -0,0 +1,20 @@
+bundle:
+  name: whl-not-uploaded
+
+resources:
+  jobs:
+    my_job:
+      name: whl-not-uploaded-job
+      tasks:
+        - task_key: main
+          new_cluster:
+            spark_version: 15.4.x-scala2.12
+            node_type_id: Standard_DS3_v2
+            num_workers: 1
+          python_wheel_task:
+            package_name: my_test_code
+            entry_point: run
+          libraries:
+            # Local wheel, prebuilt (no build: step) to keep the test hermetic. See script
+            # for the bug this exercises. Behaves the same as a wheel with a build: step.
+            - whl: ./dist/*.whl
diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/dist/my_test_code-0.0.1-py3-none-any.whl b/acceptance/bundle/deploy/readplan/whl-not-uploaded/dist/my_test_code-0.0.1-py3-none-any.whl
new file mode 100644
index 00000000000..4bb80477caf
Binary files /dev/null and b/acceptance/bundle/deploy/readplan/whl-not-uploaded/dist/my_test_code-0.0.1-py3-none-any.whl differ
diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/out.plan.json b/acceptance/bundle/deploy/readplan/whl-not-uploaded/out.plan.json
new file mode 100644
index 00000000000..da6e6cae939
--- /dev/null
+++ b/acceptance/bundle/deploy/readplan/whl-not-uploaded/out.plan.json
@@ -0,0 +1,45 @@
+{
+  "plan_version": 2,
+  "cli_version": "[CLI_VERSION]",
+  "lineage": "[UUID]",
+  "serial": 2,
+  "plan": {
+    "resources.jobs.my_job": {
+      "action": "create",
+      "new_state": {
+        "value": {
+          "deployment": {
+            "kind": "BUNDLE",
+            "metadata_file_path": "/Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default/state/metadata.json"
+          },
+          "edit_mode": "UI_LOCKED",
+          "format": "MULTI_TASK",
+          "max_concurrent_runs": 1,
+          "name": "whl-not-uploaded-job",
+          "queue": {
+            "enabled": true
+          },
+          "tasks": [
+            {
+              "libraries": [
+                {
+                  "whl": "/Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
+                }
+              ],
+              "new_cluster": {
+                "node_type_id": "Standard_DS3_v2",
+                "num_workers": 1,
+                "spark_version": "15.4.x-scala2.12"
+              },
+              "python_wheel_task": {
+                "entry_point": "run",
+                "package_name": "my_test_code"
+              },
+              "task_key": "main"
+            }
+          ]
+        }
+      }
+    }
+  }
+}
diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/out.test.toml b/acceptance/bundle/deploy/readplan/whl-not-uploaded/out.test.toml
new file mode 100644
index 00000000000..27ec2a7fcd6
--- /dev/null
+++ b/acceptance/bundle/deploy/readplan/whl-not-uploaded/out.test.toml
@@ -0,0 +1,3 @@
+Cloud = false
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
+EnvMatrix.DMS = [""]
diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/output.txt b/acceptance/bundle/deploy/readplan/whl-not-uploaded/output.txt
new file mode 100644
index 00000000000..73e36e6a842
--- /dev/null
+++ b/acceptance/bundle/deploy/readplan/whl-not-uploaded/output.txt
@@ -0,0 +1,44 @@
+
+=== bundle deploy uploads the wheel
+>>> [CLI] bundle deploy
+Uploading dist/my_test_code-0.0.1-py3-none-any.whl...
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default/files...
+Created jobs.my_job
+Files: 6 uploaded, 0 deleted
+Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
+
+>>> print_requests.py //artifacts/.internal --del-field raw_body
+{
+  "method": "POST",
+  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl",
+  "q": {
+    "overwrite": "true"
+  }
+}
+
+>>> [CLI] bundle destroy --auto-approve
+The following resources will be deleted:
+  delete resources.jobs.my_job
+
+All files and directories at the following location will be deleted: /Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default
+
+Destroy: 1 deleted
+
+=== bundle deploy --plan does NOT upload the wheel (bug)
+>>> [CLI] bundle plan -o json
+
+>>> [CLI] bundle deploy --plan out.plan.json
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default/files...
+Created jobs.my_job
+Files: 7 uploaded, 0 deleted
+Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
+
+>>> print_requests.py //artifacts/.internal --del-field raw_body
+
+>>> [CLI] bundle destroy --auto-approve
+The following resources will be deleted:
+  delete resources.jobs.my_job
+
+All files and directories at the following location will be deleted: /Workspace/Users/[USERNAME]/.bundle/whl-not-uploaded/default
+
+Destroy: 1 deleted
diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/script b/acceptance/bundle/deploy/readplan/whl-not-uploaded/script
new file mode 100644
index 00000000000..bd507766e34
--- /dev/null
+++ b/acceptance/bundle/deploy/readplan/whl-not-uploaded/script
@@ -0,0 +1,25 @@
+# A local wheel referenced by a job library is uploaded by `bundle deploy` but NOT by
+# `bundle deploy --plan`: applying a saved plan skips the build phase, which is what
+# computes the artifact upload list (phases.Build -> libraries.ReplaceWithRemotePath).
+# The job still points at the wheel's workspace path, so its run fails at runtime with a
+# missing-file error. This test pins the difference between the two deploy paths.
+
+title "bundle deploy uploads the wheel"
+trace $CLI bundle deploy
+# An import-file request uploaded the wheel to its .../artifacts/.internal/ workspace path.
+# raw_body is the wheel's binary payload; drop it to keep the golden readable.
+trace print_requests.py //artifacts/.internal --del-field raw_body
+
+trace $CLI bundle destroy --auto-approve
+# Discard destroy's requests so the saved-plan deploy below starts from a clean recording.
+rm out.requests.txt
+
+title "bundle deploy --plan does NOT upload the wheel (bug)"
+trace $CLI bundle plan -o json > out.plan.json
+trace $CLI bundle deploy --plan out.plan.json
+# BUG: no import-file request for the wheel here (output below is empty), yet the job was
+# created pointing the task at the same .../artifacts/.internal/ path that was never uploaded.
+trace print_requests.py //artifacts/.internal --del-field raw_body
+
+trace $CLI bundle destroy --auto-approve
+rm out.requests.txt
diff --git a/acceptance/bundle/deploy/readplan/whl-not-uploaded/test.toml b/acceptance/bundle/deploy/readplan/whl-not-uploaded/test.toml
new file mode 100644
index 00000000000..9325fa161c0
--- /dev/null
+++ b/acceptance/bundle/deploy/readplan/whl-not-uploaded/test.toml
@@ -0,0 +1,6 @@
+Badness = "bundle deploy --plan skips the build phase, so a local wheel referenced by a job is never uploaded and the job fails at runtime."
+
+# --plan is direct-engine only.
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
+RecordRequests = true
+Ignore = [".databricks"]