Using Classic Outlook on Windows for personal email, calendar, and contact management
We're running into the exact same issue, company wide when users are accessing Outlook through a Citrix machine their session locks up for 20-40 seconds and showing the "Outlook is trying to retrieve data from the Microsoft Exchange server" message.
Happening multiple times a day to most of the company. Only seemed to start a couple of days after this month's patch Tuesday.
I've tried everything I can think of but still no resolution.
Installing the out of band patches for the Windows Kerberos issue has fixed some of the other problems caused by the patches, but this issue persists.