Outlook 2010 won't configure exchange account, 0kb .ost file

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Outlook version
Outlook 2010 32 bit
Email Account
Exchange Server
Since we began transitioning our users onto exchange (2010), we have run into the symptoms below 6 or 7 times.

User will have the e-mail account set up on their computer and working. At some point Outlook 2010 will suddenly be unable to connect to exchange. We haven't tracked down what triggers it. When we delete the account and re-add it, the setup gets through the first two checkmarks "Establish network connection" and "Search for <user's e-mail address> server settings" then locks up when trying to "Log on to server". I say lock up because the gradient progress bar at the top will stop moving and the window becomes unresponsive. It will hang there for 5-10 minutes and then error out saying "the connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action".

However, we are able to add our test account (that's on the same domain) onto that same computer, so it is not a network/DNS/general Outlook problem. And I am able to add the user's account on other computers, so it is not an exchange/AD/account/server-side problem. It seems to be something specific on that computer when Outlook tries to configure that specific e-mail account. It is finding the server and authenticating on it, I know this because if I use the wrong password it will prompt me for it again (proving that it found the server and wasn't able to log in), and when I type it in right it goes for a second or two before locking up. It is failing before it gets to the point of creating/downloading the xml configuration file in the app data where the ost/pst files reside. Outlook's built-in "Test Email AutoConfiguration" tool does complete successfully with the user's account info on the user's computer.

A few other details: I can get all three green checkmarks if I delete the account, open Outlook, go to file and account settings and add it there. But it doesn't so the whole setup there, just connects to the server. It tells me to restart Outlook to configure the account, and when I do that it either hangs at Loading Profile or sometimes at Processing. It gets to the point where it tries to create the .ost, but doesn't get past creating a 0kb file.

I renamed the whole Profiles key in the registry under Windows Messaging Subsystem or whatever it was called, deleted all the .ost/.xml/etc files associated with the account, renamed the account folder under %appdata%/Microsoft/Protect/, and tried starting Outlook in safe/resetnavpane/noextensions/etc modes, all with no change in the symptoms. Except that if you start in Safe Mode Outlook will actually start to open, but as soon as the UI starts to form it will lock up and eventually error the same way. It's like safe mode tries to load the UI before configuring the account, but as soon as the .ost file starts to generate it will lock up and the task needs to be ended.

I can't seem to figure out what file/key/process/etc is interfering with the configuration.
Nope, there aren't any credentials saved in there. It does seem to be related to the credentials though. If I add the account via Outlook and then go in and hit Check Names from control panel it asks for the password. It seems like it should have it saved by now, I know I hit "remember credentials" the last few times it asked. Though outlook does have problems believing you when you hit that box.
It sounds like credentials to me too. Is the user logging in automatically with her windows credentials or entering them in outlook separately?
Separately. They're external users outside of our domain.

Using netmon I can see that while the Control Panel Mail app is locked up trying to configure, it is still talking to the server. The server sends some info and the pc responds, but it's on a loop like it's not working and it keeps trying. Happens every 30 seconds or so, server sends some packets, pc instantly responds, wait 30 seconds and repeat, etc until it times out and fires the error about connecting. It's SSL so I can't see what credentials it's passing, though.
Any thoughts? Is there a way to make Outlook write a verbose log of its setup/login/configuration process?
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