We are currently undergoing some testing for an upcoming Exchange-to-Cloud migration of the staff at our university. Previously, we migrated all of our students without hearing of any specific configuration issues (most likely due to the fact that we had them deleting their Outlook profiles and setting them up from scratch).
With our current migration we want the users to be able to log on and have their reconfiguration done more or less automatically via autodiscover.
We set up a couple of accounts on the exchange environment previous to the migration to test the post-migration user experience.
The one issue we have which is universal for all of our test-environments (both standalone and domain-joined accounts on Outlook 2007 and 2010 on Windows XP) occurs when the mailboxes manage to connect to the Microsoft Exchange server, either automatically or via the 'E-mail account repair' function,
Once connected, Outlook, as it should, informs the user that "The Microsoft Exchange administrator has made a change that requires you quit and restart Outlook"; after restarting the client, the user receives a message stating that;
"Outlook is using an old copy of your Offline Folder file (.ost). Exit Outlook, delete the .ost file, and restart Outlook. A new file will be automatically created the next time you initiate a send/receive."
The easy solution to this issue is obviously just to remove the .ost file.It's not that we don't trust our fellow colleagues technological abilities, but we are trying to make the configuration process as easy as possible for them in order to relieve the helpdesk support team from the possibility of getting overloaded (we are going to migrate ~20,000 users).
Having roamed through various Microsoft and tech forums I have failed to find any case similar to ours. We are using both VMware Virtual Infrastructure and Oracle VM VirtualBox Manager for the testing.
The test-mailboxes are not abnormally large, but ranging from 200-300 MB with around 3,500 items each. We are not copying Outlook content from one computer to another.
What I would like to know is if there is any way to avoid this issue, or whether it is required to either completely reconfigure the client (i.e. removing the user accounts and setting them up again)?
Any response is appreciated.