We’re rolling out Docker Desktop (Enterprise level) across a large Windows and Mac fleet using our internal deployment/MDM tooling to push installs and updates, and running into two recurring issues. Curious if others have hit the same thing or if there’s a documented best-practices checklist we’re missing.
Windows: A large share of new installs fail on first launch because WSL2 and/or the Virtual Machine Platform Windows feature weren’t enabled before Desktop was deployed — errors like “WSL update required,” “Virtual Machine Platform not enabled,” and “WSL is not installed.” A smaller number of previously-working machines break right after auto-updating to a newer Desktop version.
Mac: After a fleet-wide update push, some machines show “Docker.app is damaged and can’t be opened,” even though our deployment tool reports the update as successful. Logs show ditto ... Operation not permitted errors and exit code 7 during the in-place app replacement.
Question for the community: Is there a recommended pre-install/pre-upgrade checklist for validating WSL2/virtualization prerequisites on Windows before deploying at scale, and for safely automating Mac updates without risking a corrupted app bundle? Would love to compare notes with anyone else managing Docker Desktop across a large fleet.