Outlook 2007 under Windows XP connecting to Exchange 2003 SP2: when started, it flips back and forth between "Connecting to Exchange Server" and "Disconnected" three or four times, then gives up and stays disconnected.
I tried deleting the ost file (which was nearly 2GB), turning Cached mode on and off, recreating the account inside the Mail control panel, changing the account to use HTTP, and probably some other things. None of it seemed to make any difference, until …
After fiddling with it for a while, I got this absurd error message dialog at startup, and it exits after I click OK:
Cannot start Microsoft Office Outlook. Cannot open the Outlook window. The set of folders cannot be opened. Microsoft Exchange is not available. Either there are network problems or the Exchange server is down for maintenance.
(I'm not sure if I can even trust that message. It's so long, it just feels like a random offset into Outlook's stack of error messages.)
Either way, the Exchange server is available to everyone else, and is available via OWA from that computer. I ran Process Explorer against Outlook and it showed 5 or so ESTABLISHED connections to our Exchange server, plus listening on two UDP ports, and two CLOSE_WAIT connections to localhost. If I managed to look at Outlook's IP connections while it was doing its Connecting/Disconnected dance, it had a huge number of connections open to the Exchange server. It more than filled ProcExp's dialog box; I'm guessing at least 20, probably more.
The only other odd thing is that our network admin at some point added a wildcard DNS record to the domain name that we use for email, and now Outlook will sometimes (always?) start by complaining about autodiscover.example.com's SSL certificate. There is a web server there, but it doesn't have any sort of email autodiscover anything on it. It doesn't make any difference if I click "OK" or "Cancel" (or whatever the buttons are). I also added a bogus entry for the hostname to Windows' hosts file, pointing it at 127.0.0.2, and it stopped complaining about the certificate. (The CLOSE_WAIT sockets above were from before I made this change, and went away after.) I don't think this is related, as the same problem should exist for everyone, but it might be.
This is the second time this user has had this problem. The first time, I never found a solution other than reinstalling Outlook. Now that it's a pattern, I'd like to find a permanent solution, rather than assume it's a random glitch.
The user's Outlook started working again, partially, last night while at home connected to the office via VPN. It's unclear how much of the "partially" is due to me screwing around with his account settings. Probably a large portion. That said, once I recreated his account settings properly this morning, he says that a large number of folders were moved around. Honestly, this feels to me like user error, but it might also be a symptom of the problem.
I'll have to come back to this if and when the problem crops up again.