I am in the process of upgrading from Exchange 2010 to 2013. Odd issue I was hoping to get help with.
I have migrated my own account, and it was looking great. It finished while I was at home (off corporate network). I logged into Outlook 2013 and it said a change was made, restart. Excellent, the migration worked and I am getting pointed to the new server. Reload Outlook and it seems to go great - re-checks the sync on all folders. Then it gets to "Updating Address Books". I leave it alone for 25 minutes and when I get back, its still stating its updating. During this time, no other send/receives run so I can't get inbound mail. I try a manual download of the Address Books, nothing... it just sits there. Close and reopen Outlook, same result.
So - I get on the VPN, load Outlook - it gets to the Updating Address Books step, and works! I then do a manual download of the OAB and the job runs fine. After the updates ran, I got back off VPN and Outlook worked again as it was satisfied it had the latest OAB, but manual downloads still failed.
Any ideas? Nothing in firewall logs, but that seems unlikely.
Summary - over the internet updates of OAB fail, on network updates of OAB succeed.