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Two issues prevented the detached update helper from completing: 1. Only CREATE_NO_WINDOW was set — the child cmd.exe process was still attached to the parent console session and got killed when the terminal closed. Add CREATE_NEW_PROCESS_GROUP to fully detach it. 2. `timeout /t 1 /nobreak` requires a console and fails silently in a no-window context, causing the retry loop to spin with no delay. Replace with `ping -n 2 127.0.0.1` which works in any environment. Co-authored-by: Cursor <cursoragent@cursor.com>