WireGuard for Windows failed to start after update to v0.2.1

[Jason A. Donenfeld]

On 11/17/20, Joshua Sjoding <joshua.sjoding at scjalliance.com> wrote:
> Here's a more complete view of what happened:
>
> 1. I heard reports of two of our users having issues updating
> WireGuard this morning. Their issue was a firewall warning (now
> hopefully resolved in a separate thread).
> 2. I decided to try updating WireGuard on my own laptop to see if I
> got the same behavior.
> 3. I opened the WireGuard UI through the icon in the system
> notification area and saw that WireGuard was offering me an update.
> 4. I told Wireguard to update and it started to go through the usual
> update process.
> 5. The WireGuard UI closed and the icon in the system notification
> area disappeared, which is typical as it does an update.
> 6. The WireGuard UI never came back and the tunnel never came back up.
> There were no error messages, just silent failure.
> 7. I checked the Windows application log and saw the error messages
> listed earlier. In particular this message seemed pertinent: "Product:
> WireGuard -- Wintun error: Unable to remove existing driver: The
> system cannot find the file specified. (Code 0x00000002)"
> 8. I compared my experience with the other two cases and determined
> that mine was different. I started this thread and another on the
> WireGuard mailing list to address the issues.
> 9. I had some tea. I love tea. Tea is wonderful.
> 10. I manually started the WireGuard desktop app. It immediately
> prompted for elevated privileges, which is atypical. I provided it
> with administrative credentials.
> 11. The WireGuard UI opened and the icon appeared in the system
> notification area.
> 12. I saw that WireGuard was missing my configured tunnel. It was also
> still prompting me to update it, which was very surprising.
> 13. I told WireGuard to run the update again.
> 14. The UI closed as the update took effect, but this time it opened
> back up on its own after the update finished, which is what usually
> happens. I saw that the icon was present in the system notification
> area as well.
> 15. I saw that my tunnel configuration was back, but the tunnel was
> deactivated.
> 16. I activated the tunnel and everything was happy again.
>
> If the MSI system was supposed to rollback in the case of failure, it
> failed to do so. Perhaps the MSI system thought the update succeeded
> when it didn't? I found it odd that the MSI reported that it had
> installed the product immediately after it reported that it had
> failed.
>
> Here are the events from the Windows Application event log again for
> convenience, taken at step 7, in order of occurrence:
>
> ----
>
> Error, Event 1013, MsiInstaller, 11/17/2020 8:41:49 AM
>
> Product: WireGuard -- Wintun error: Unable to remove existing driver:
> The system cannot find the file specified. (Code 0x00000002)
>
> ----
>
> Error, Event 1013, MsiInstaller, 11/17/2020 8:41:49 AM
>
> Product: WireGuard -- Wintun error: Failed to uninstall driver: The
> operation completed successfully. (Code 0x00000000)
>
> ----
>
> Info, Event 11708, MsiInstaller, 11/17/2020 8:41:49 AM
>
> Product: WireGuard -- Installation failed.
>
> ----
>
> Info, Event 1033, MsiInstaller, 11/17/2020 8:41:49 AM
>
> Windows Installer installed the product. Product Name: WireGuard.
> Product Version: 0.2.1. Product Language: 1033. Manufacturer:
> WireGuard LLC. Installation success or error status: 1603.
>
> ----

Thanks. We've reproduced this, understand the race condition that led
to it, and are working on a fix for 0.2.2. Turns out to be quite
tricky MSI internals at play. Your detailed reports were extremely
useful. I'll keep you posted when we have a fix confirmed.