Mac Cannot "Remote Desktop" to Freshly-Started Windows - A Classic "Catch-22"
This behavior is a classic “Catch-22” involving how Windows handles security and how the Mac version of the Windows App (formerly Microsoft Remote Desktop) manages connections compared to its Windows counterpart.
The most likely reason this happens is that after a restart, your remote PC is sitting at the Windows Login Screen. In this state, two things are often true:
The VPN Gap: GlobalProtect may not have established its tunnel yet (it’s waiting for a user to log in to “start” the session).
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