Hi
Welcome to Centrify Community!
According to your desciption, it seems to be an issue between Mac's Keychain and Microsoft outlook itself.
As Centrify Smartcard tool is used to perform the authentication part for the user to access into different applications on the Mac. While the Outlook will store the user's credential into Mac's keychain in case it needs to use it in the future.
From your situation, it seems like the Outlook is not able to store / find the stored user information and therefore everytime it needs to authenticate, it will prompt for the PIN repeatedly.
As I have done some further research online and able to find multiple similar issue reported to Microsoft Support as follow:
Therefore, I would suggest you rasing this issue to the Microsoft Support for any further assitance and have a better understand on how their Outlook and Keychain works together.
Hope it helps!
BR,
Ivan