Yes, the settings of ActivClient can impact whether Cisco AnyConnect prompts for a PIN or not. If ActivClient is set to CachePIN, it generally means that ActivClient is remembering your PIN so that you don't have to re-enter it for subsequent authentications. This could potentially result in Cisco AnyConnect not prompting for the PIN.
However, caching the PIN is typically not recommended for security reasons, as it can potentially allow unauthorized access if somebody else gains access to your machine. It would be advisable to disable the CachePIN setting in ActivClient to ensure that Cisco AnyConnect prompts for the PIN as expected.
You may also want to check the settings of Cisco AnyConnect to ensure that it is configured to use the relevant CAC (Common Access Card) certificates for authentication, as this could be another potential reason why it's not prompting for a PIN.
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