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SBS 2003 smtp relay not authenticating

Posted on 2014-09-21
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Last Modified: 2016-06-14
We re ran the Small business Internet Connection wizard and now our smtp relay has stopped working. It was working before the re-run.

It was sending using an authenticated relay service provided by our ISP.

We get messages stating it has failed authentication. The ISP has tested the account and can connect using the name and pass we have so feel that is not the issue.

They have suggested changing the greet time but not sure where to do that.

Was wondering if there is a way to reset the smtp connector completely, or any other suggestions welcome.
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Question by:dbhsupport
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by:Davis McCarn
ID: 40335706
Restoring the system state from a backup dated before you made the changes is about your only hope.....

This would have rescued you and will if it happens again: http://www.computer-help.net/Best-Registry-Backup.html
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by:Cris Hanna
ID: 40335769
And what was your reason for re-running the wizard?
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by:dbhsupport
ID: 40336039
We re-ran it to update DNS as ISP had changed theirs.  We can email the ISP but if we try to email anywhere else we get the message "Relaying denied.  Proper authentication required".  When we ran the wizard the relay credentials were reset and we had to enter the Basic Authentication username/password again - these have been verified by ISP. We wondered if running the wizard would reset anything else to do with the relay, so far we have not been able to find anything. Thanks.
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Expert Comment

by:Alan Hardisty
ID: 40336089
Check the settings on the Smallbusiness SMTP Connector using the Exchange System Manager and on the Advanced Tab> Outbound Security button, make sure you have the correct credentials registered and have Basic Authentication enabled (or whatever you need),

Then restart the SMTP Service and test mail-flow.

Alan
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Author Comment

by:dbhsupport
ID: 40336256
We have already done this thanks.  We were wondering if there was any other component that the Internet Connection Wizard might change when it gets run? All settings on the SMTP connecter are as they were before but we still get the error when sending.
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Expert Comment

by:Cris Hanna
ID: 40336267
Is there a particular reason you need to send through the ISP?
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BlueCompute earned 500 total points
ID: 40336393
Should be trivial to troubleshoot; god only knows why people are suggesting a System Restore, that's using a sledgehammer to crack a nut...
First of all, test plain SMTP over telnet to confirm the failure message is what's expected and you're seeing. The expected result is that mails with RCPT TO at your ISP would be accepted, all others rejected with the same message Exchange is logging.
Then attempt Authenticated SMTP over telnet - you'll need to use a Base64 converter to get the user/pass in the correct format. The expected result here is sucessful authentication, and RCPT TO being accepted for *any* email address.
If this doesn't work, your ISP are wrong about it being set up correctly, or more likely you've got a typo in a username or password somewhere. If it does work, use WireShark to monitor an SMTP transaction made by your exchange server. Compare it to the one you did manually with Telnet, note any differences and either fix them or post them back here.
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