CRM Outlook Plug In not filtering "Look in" to changed "Look For"

Hello,

When one of our users tries the Set Regarding in the Plug In for Outlook, and they change the filter for "Look For" from Account to Opportunity, the screen doesn't update the "Look In" or the screen below.

This same user, when looking at the CRM option in Outlook > File > CRM, the "About" won't open.

If we open the actual Plug In we can see records fine here.

Any suggestions for troubleshooting?

Thanks,

Brianna