Home Assistant writes an OS update and leaves the reboot to someone, so a scheduled one never finished unattended. The schedule now asks for the reboot once, follows it through Home Assistant going away, and counts it done when the Supervisor reports a different version with nothing pending. A machine that doesn't come back or falls back to the old version fails after 20 minutes, which ends the slot and raises update_failed. Install on the page and through MCP still leave the reboot to the person. Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>