I recently migrated from Exchange 2010 to Exchange 2013. This client has a main office housing the Exchange server, and a number of satellite offices connected together with VPN routers. Before the migration, everyone was connecting to the server with Outlook, but after the migration, because of the version of Outlook installed on many of the PCs at the satellite offices are connecting using OWA. One of the satellite offices has Outlook 2013 on all of their PCs, and interestingly enough, they all connect using the same user, so they're all checking the same email address.
I spent some time trying to troubleshoot 2 PCs at this satellite office yesterday, one of them connected, and the other I never got to connect. I ran outlook with a number of command switches disabling add-ons and the like, removed the profile and added it again, and I just could not get this thing to work. I sent an e-mail in the morning that was just stuck in the outbox, and just got them on OWA until I could spend more time on it, and I left Outlook connected. Later on that night, I received the e-mail. It's like it connected on it's own nearly 10 hours later. This morning, there's 3 PCs not connecting. The curious thing here is they're PCs that we thought were connected yesterday, but Outlook indicates the inbox was last updated on 10/30, that would have been 4 days ago. This would have been when we migrated Exchange mailboxes.
Another curiousity. If I add another profile to outlook connecting as the same user, I get an error message: "Cannot start Microsoft Outlook. Cannot open the Outlook windows. The set of folders cannot be opened. You must connect to Microsoft Exchange with the current profile before you can synchronize your folders with your Outlook data file (.ost)." If I add another profile with a different user, it connects immediately and syncs with no problems.
I'm not sure if there's a limit to how many concurrent connections a user can have with the server, and I'm reaching that limit, or if there's something else going on that I'm missing. Can you help me troubleshoot this issue?