I'm having the same problem where a machine won't run the login script, and then later it will. Network connectivity is fine (another machine on the same hub gets the script without issues). Is there any way to log what's happening during the login?
Part 2: By default, logon scripts run as a background tasks. As a troubleshooting step, you can try using the Start.exe command-line tool to run local and domain logon scripts as a foreground process, as explained in MS KB article 265016, How to run a domain logon script in the foreground with the Start.exe command-line tool.
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