SMTP Alias change = Dead Address

I received word that our Director was not receiving mail properly last week. He had two SMTP addresses listed, one for Joe.Director@domain.com, and one for Joseph.Director@domain.com. Apparently, he had been able to get mail sent to Joseph, but not Joe. We checked several things, found the setting in Exchange Management Console that allowed us to choose the primary SMTP address, disabled the policy setting (since it wasn't allowing us to change the primary when the policy was enabled), and set it from Joe.Director (which it was set at) to Joseph.Director (which was what we wanted it to be). We also went out to our ProofPoint server and made sure emails could get to both addresses. Sounds good, right? Not so much.

Neither email address can receive or send mail now. Several test messages have disappeared into the aether (strangely, I don't get NDRs from them) and email goes nowhere from his Outlook client and his Blackberry. I'm at the point that I am planning to back up and then delete his mailbox and recreate it, possibly even to the point of deleting his user account in AD and starting from scratch there. Is there anyone out there who has any ideas of what I can do to solve this? Thanks in advance, and good luck...
MCHCPAnalystAsked:
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B HCommented:
did you re-enable the policy?  with it disabled, your exchange server won't really want to accept emails for that domain

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MCHCPAnalystAuthor Commented:
Sorry, I wrote that wrong. The policy is enabled for the organization, we just disabled it for the particular user.
B HCommented:
so what happens if you try to send a manual test email to him?

telnet servername 25
helo whatever.com
mail from: joe@whatever.com
rcpt to: joe.director@domain.com
data
subject: test1
test1
. (end with enter-dot-enter)

then do another for the other email... what errors do you get?
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MCHCPAnalystAuthor Commented:
Well, I'm not sure what this means, but everytime I try and type something in on the "mail from:" line, I get 530 5.7.1 Client was not authenticated, and it boots me out of the telnet session. Am i doing something obvious wrong?
B HCommented:
no, but if you're expecting to receive public email, then that is your problem...

your smtp server is set up to only accept emails from authenticated users...  

meaning, if i go email you from yahoo, it won't get to you, because yahoo isn't authenticating

MCHCPAnalystAuthor Commented:
Hmm...I understand your logic, it makes sense, but I am receiving email from external sources - just not to this address. Internal email is also not reaching the address. But everybody else is having their mail delivered.

I really do appreciate your help...
B HCommented:
do you have some outside 3rd party spam filtering service that receives your mail, filters it, then shoots it into your exchange server (authenticated)?

look up the MX and A record for your domain, does it point to your mail server's outside ip address?
MCHCPAnalystAuthor Commented:
Yeah, that's what the ProofPoint server is. MX records for our domain point to the ProofPoint device.
MCHCPAnalystAuthor Commented:
Um, with a rather sheepish expression I state that I found the problem was a communication problem between the Director's secretary and myself. She said that "he's not getting his emails", which I took to mean no email traffic at all, but she was indicating that the problem was with his BlackBerry only. It's a BES issue or something, so I'll give you the points for working on it even though there wasn't really even a problem to begin with. Thanks!
B HCommented:
hah i love users more and more every day.

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