We are in the middle of moving from a local exchange server to using Microsoft hosted mail. Currently, both our local mail and office 365 mail are active. As an intermediary step, I am attaching both accounts to our current version of outlook (2010), so that people can move mail through Outlook at their own pace. So far, I've set this up a dozen times with minimal issues, but I have run into a strange problem.
One user's outlook fails repeatedly to add the account. It acts like it's working fine, but when outlook requests the password, my user types it in, and the box requesting the password pops up again. If told to cancel, an error pops up, stating that the exchange server cannot be found, and that outlook needs to be online. I neglected to get the complete message, but that is the gist.
The same email can be setup on a different machine, and the password is correct because it was used to set up one drive on the same machine. I even tried creating a new mail profile, but it also had issues. The problem has to be with that installation of outlook, specifically, and possibly the user profile. This user has had a lot of issues with their outlook before, sometimes due to data size issues (too many names in the junk list, just flat too much email, period).
They currently have a lot of .pst archived folders attached to outlook as a compromise to keeping the inbox small, and I'm wondering if this could have any impact. Has anyone heard of this problem, or have any suggestions?