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I recently transferred one of my domains to a different registrar. I updated the name servers to point to the right location, and then went through the process of recreating all of the mailboxes, then updating the passwords in exchange's POP3 Connector.

Easy enough, I thought. However, exchange is no longer downloading mail from the mailboxes. Upon checking the server logs, I notice that the error is pretty obvious:

ERR: AUTHENTICATION FAILED

I can logon through webmail perfectly fine so I know for a fact the passwords work, but I reset them just for good measure and I reset them to something extremely hard to screw up: abc123.

I then figured I'd telnet into the mailbox to see if I can authenticate that way, but no dice. Same error.

But here's the really weird thing: I can set any of the accounts up in a pop3 client (I use thunderbird) and it works perfectly fine.

I feel like I'm missing something extremely obvious here. Can anyone explain what's happening here or, better yet, suggest what I can do to resolve the issue? I'm all out of options.

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This isn't an answer, but why aren't you using Exchange the way it was intended to be used? Why have your email queue up on an external server and then have Exchange fetch it and deliver it to your user mailboxes when email can be delivered directly to Exchange, not too mention the issue you're currently having. –  joeqwerty Aug 17 '12 at 1:43
    
Mostly because I took this server over from another tech and this is the way it was set up, so I figured I didn't have to do anything short of recreating the mailboxes and changing the passwords in exchange... but also because I'm a huge noob when it comes to Exchange and running my own email server in general and this set up is easier (apparently not?). –  Mark Rawlingson Aug 17 '12 at 1:53

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