Fleet reports error when Xcode is successfully installed through VPP

[ddribeiro]

Fleet version: Fleet 4.76, tested on Dogfood SNAPSHOT-16fd8b1

Web browser and operating system: macOS 26.1

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💥  Actual behavior

Xcode installs via VPP seemingly always report as failed in Fleet, even when the installation is successful on the host. This happens even when the installation completes in less time than the FLEET_SERVER_VPP_VERIFY_TIMEOUT is configured to.

For example, with the FLEET_SERVER_VPP_VERIFY_TIMEOUT set to 20 minutes in Dogfood, I initiated a VPP install of Xcode to my host. I monitored my /Applications folder and Activity Monitor to observe install progress. The install completed successfully after 10 minutes, but the install action remained in my host's "Upcoming" activity tab until the VPP verify timeout was hit, at which point it moved to my host's "Past" activity tab with a failed status.

🛠️ To fix

If the app is installed on the host, it shouldn't show a failed status.

🧑‍💻  Steps to reproduce

These steps:

• Have been confirmed to consistently lead to reproduction in multiple Fleet instances.
• Describe the workflow that led to the error, but have not yet been reproduced in multiple Fleet instances.

1. Set your FLEET_SERVER_VPP_VERIFY_TIMEOUT to 20 minutes. This ensures that the Xcode VPP install will likely complete before hitting the timeout.
2. On your test host enrolled in a team that has Xcode available, initiate an install from Xcode. In my test, I initiated from the admin side, but I suspect the behavior is the same for self-service.
3. Observe your host's /Applications folder and watch the CPU tab in Activity Monitor to monitor the install. The installd process will spike CPU during the install and stop when it's completed.
4. After the install completes on your host (assuming it finishes before the VPP verify timeout), go back to your host's details page in Fleet and see that the install event still appears as an "Upcoming" activity.
5. Wait the remainder of the VPP verify time, then refresh your host's details page. The install event will appear in "Past" as a failed install.

🕯️ More info (optional)

We originally suspected this because the install was taking longer than the FLEET_SERVER_VPP_VERIFY_TIMEOUT, which defaults to 10 minutes. However, we tested several scenarios, and it seems the install always reports as failed, even when the install completes well before the timeout.

[Sampfluger88]

Linked to Unthread ticket:

Conversation #10652

[mna]

Will pick this to try to repro and figure out what the fix could be (we're short on tickets in the queue for the sprint). Leaving it in drafting board too so it can get the estimate.