Cisco AnyConnect on my work machine has this annoying property where, sometimes, when I wake the machine from a short sleep and attempt to login to the VPN again, it tells me that something is wrong with the certificate and it refuses to connect. After you wait a few minutes... all is fine.

@me I have guesses that I am not motivated enough to explore, but I didn't mention that it's macOS, so there could be something weird with how it tries to access the keychain.

Losing track of time is another possibility.

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