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Are the old servers more or less the same? New servers are in the same OU with same GPOs applied and configured similarly?

nah the old servers didnt have fsl and were 2008r2. so its all new. now for the new servers, we do have similar ones with the same policy linked. those do not have issue.

so the users that are having issues, you have to blow away their profile? But they are net new profiles to begin with?

Correct, new users. Outlook works first time they log in. Subsequent logins, outlook may or may not be broken. I do see in the log file that it cannot find the setting for Outlook cache mode and using the default of 1. (FSL Log). We are in Online mode though and not sure if that particular setting is causing it. I also thought it was related to shared mailboxes and a pst file not being saved with the profile. idk