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SBS 2011 SMTP Connecter stopped working for email sending

Posted on 2014-01-23
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Last Modified: 2014-02-03
I have a SBS 2011 server.  Users have started getting a delivery delayed message overnight.
The are sending via SMTP.DOMAIN.COM (DOMAIN is there domain obviously).  But it is coming up saying Last Error is

"451 4.4.0 Primary Target IP address responded with "451 5.7.3 Require basic authentication.

This is odd as no setting have changed and it is setup to use basic authentication from the day it was installed.

When I try to see what is in the queue I get

"The remote pipline has been stopped.  it was running command 'get-message - ResultSize '1000'- ReturnPageInfo $true - server 'SERVERNAME.DOMAIN.local; - Sort Order '-From Address' - SearchForward $true - BookmarkObject $null - BookmarkIndex '-1' - IncludeBookmark $false"

Which I have never seen before.

I have tried moving them to a new smtp details on a completely different server which another SBS 2011 server I have is using fire with the same error occurring so I don't think its the external SMTP service.

Ideas?
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Question by:betoni
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by:Qwadrat4
ID: 39802619
I think if target server asks you for basic auth, you should set your send connector with some credentials.
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by:Olaf De Ceuster
ID: 39802629
Did you check you smarthost settings in the sbs console?
ISP probably requires auth now?

Also run the BPA to check for most common issues.
http://support.microsoft.com/kb/2673284

Hope that helps,
Olaf
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betoni earned 0 total points
ID: 39802636
Apologies a little embarrassed just as a clicked submit I realised it was most likely that the IP had been listed for Spam.  So I checked on http://www.spamhaus.org/ and yes it was int eh CBL.

So I have made the following changes and marked it for delisting.

1. Added a firewall rule to only allow port 25 from the server IP address.
2. Running AV and Malware bytes on all client PCs/laptops.

Anyone got any other suggestions?

If nothing else I hope this post will be useful to others with the same problem.  - thanks to Olaf for trying to help!
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Author Closing Comment

by:betoni
ID: 39829067
I figured the issue out.
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