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550 IP Authorization check failed - psmtp (in reply to RCPT TO command)

Posted on 2012-08-29
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Last Modified: 2012-11-30
We have Exchange 2010 and some users configured forwarding to their outside Gmail addreses. However, in some instances the Exchange server would generate the following NDR: Diagnostic-Code: smtp; 550 IP Authorization check failed - psmtp

I believe the filtering has been configured on Gmail to allow e-mails from our Exhange and it is woking for straight messages - Exchagne to Gmail. However, it does not work if the path is Outside user - Exchange - forward to Gmai. Then, Exchange will produce the error above
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Question by:exhuser
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11 Comments
 

Author Comment

by:exhuser
ID: 38355360
It appears that there are multiple headers and Gmail Postini will not accept if one of the headers contain its own domain name...
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Expert Comment

by:Manpreet SIngh Khatra
ID: 38355419
So what are you planning to do ?
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Author Comment

by:exhuser
ID: 38355452
Is there a log file on Postini where I can see what is being rejected and why?
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LVL 37

Expert Comment

by:Jamie McKillop
ID: 38421448
Hello,

The problem you are running into is anti-spoofing. Your users are redirecting the email so when the email is received by Postini the from address is the original sender, whis is an SMTP domain that Postini is authoritative for. Postini will then reject the message because the sending SMTP server (your server) is not authorized to send for that SMTP domain.

The only way to get around this issue would be to change the Outlook rules so that the message is forwarded instead of redirected. When the message is forwadred, the From address would be your user's address. The drawback to this is that the user then cannot reply by just hitting the reply button as this would send it back to your server. The user would need to change to To field to match the original sender.

JJ
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Author Comment

by:exhuser
ID: 38434017
I believe we have it configured as forwarding on the Exchange server (with local copy.)
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Expert Comment

by:Jamie McKillop
ID: 38434038
Right, so what I posted above still stands. Even thought it says "forward" on the checkbox, it is really a redirect as the from address is still the original sender.

JJ
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Author Comment

by:exhuser
ID: 38434067
So, you suggest to enable forwarding on the client side?
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Expert Comment

by:Jamie McKillop
ID: 38434083
That is the only way you are going to get around this. If you forward on the client-side. it will actually be forwarded and the From address will be your user instead of the original sender.

JJ
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Author Comment

by:exhuser
ID: 38434120
The problem is that the client has to receive it first. If the client has no access to e-mail application, then nothing will be forwarded...
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Accepted Solution

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Jamie McKillop earned 1500 total points
ID: 38434280
The forwarding rule is server-side, so there is no need for the client to be connected.

JJ
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