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Some external email rejecting to valid recipients

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Some external email rejecting to valid recipients - 23.Oct.2010 2:03:06 PM   
sprinsen

 

Posts: 3
Joined: 23.Oct.2010
Status: offline
Hello, we have been experiencing a strange problem with our Exchange 2000 server for a few months now but recently it has started to become a bigger problem.

When sending emails to SOME addresses on our main domain we get this reject message (this is from gmail but i get a similar response when I use my yahoo account to send the mail.  I replaced or removed my real email addresses with dummy account info):

<begin message>

Delivery to the following recipient failed permanently:

    test@domain.com

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 550 550 Invalid recipient <test@domain.com> (#5.1.1) (state 14).

----- Original message -----

MIME-Version: 1.0
Received: by 10.42.79.212 with SMTP id s20mr1411740ick.95.1287719300871; Thu,
 21 Oct 2010 20:48:20 -0700 (PDT)
Sender: (my valid gmail account)
Received: by 10.220.71.143 with HTTP; Thu, 21 Oct 2010 20:48:20 -0700 (PDT)
Date: Thu, 21 Oct 2010 23:48:20 -0400
X-Google-Sender-Auth: a4J1ARIla8o1RAmQGTmWkwZS08I
Message-ID: <AANLkTimRSznNEZ31SKTa7stf6ABMnW23UJnC3D2PqyMP@mail.gmail.com>
Subject: test from gmail
From: (I removed my external email address)
To: test@domain.com
Content-Type: multipart/alternative; boundary=20cf3011d90f7fb50504932c83a2

<end message>

This test@domain.com account (not my real domain obviously) is a secondary address I gave myself under my regular AD account.  I can send emails to my main address but not to this secondary address so I know my account can receive mail.  However there are some users who are rejected even if the mail is to their primary address (in fact several only have the one main email and it rejects every time) so I know it is not a primary vs secondary email address issue. I have also swapped the primary/secondary emails under my account and it made no difference, I could still send to the main address but the "test" account fails.  Furthermore, we have a second domain routing mail through this same exact mail server and all of those email addresses seem to work fine.

I have tried to edit Recipient policies in Exchange to no effect (which seemed to make sense since I can receive some mail to my account).  I've tried deleting addresses and adding them back in to no effect.  I've tried all sorts of changes to Exchange (to the point of actually breaking mail all together, then fixing that but still having this same problem).  There are also no problems when sending mail internally, this is only an external email issue.

I'm at a loss to figure out why this is happening.  If anyone can shed some insight into this issue and point me in the right direction I would be very grateful.

Steve
Post #: 1
RE: Some external email rejecting to valid recipients - 24.Oct.2010 6:14:50 AM   
Jesper Bernle

 

Posts: 912
Joined: 15.Oct.2007
Status: offline
Have you configured a Recipient Policy and marked the domain as Authoritative in your organization for the domain names you want to accept incomming emails on?

(in reply to sprinsen)
Post #: 2
RE: Some external email rejecting to valid recipients - 24.Oct.2010 5:43:26 PM   
sprinsen

 

Posts: 3
Joined: 23.Oct.2010
Status: offline
Hi Jesper, thanks for responding.

In my recipient policy list I have 3 entries:

Highest priority is my primary domain which includes my main email domain as the only SMTP email policy.  This is the one that seems to reject some email addresses despite the fact that they are valid and correctly implemented on the user side.

Second entry is my secondary organization which has it's own email domain listed as it's only SMTP email policy.  These all seem to work fine.

Lowest priority is the default policy which also has the same email domain as the highest priority policy (my main domain that is having the problem) as it's only SMTP email.  I'm not sure why that is like that (I didn't build this server so I'm not 100% certain why that is listed as such) but that the fact that SOME email to the main domain gets through led me to believe that the policy was not likely to be the problem, I would have expected that all addresses would fail if it was a recipient policy issue. 

Is that an incorrect assumption?

As for making it authoritative I'm not sure exactly what you mean but both the top 2 priority SMTP policy have the "This Exchange organization is responsible for all mail delivery to this address" option checked.  I'm not sure what else you might be referring to but again I would think all mail would fail if that was not set correctly, perhaps that is an incorrect assumption as well?

It almost seems as though some of my email addresses are either on some sort of blacklist in Exchange or are missing from some sort of whitelist but to my knowledge neither of those exist.  Is there some sort of address book that needs to be edited that I am completely missing?

Thanks again for your help.

Steve

(in reply to Jesper Bernle)
Post #: 3
RE: Some external email rejecting to valid recipients - 25.Oct.2010 4:28:42 AM   
Jesper Bernle

 

Posts: 912
Joined: 15.Oct.2007
Status: offline
quote:

ORIGINAL: sprinsen

Hi Jesper, thanks for responding.

In my recipient policy list I have 3 entries:

Highest priority is my primary domain which includes my main email domain as the only SMTP email policy. This is the one that seems to reject some email addresses despite the fact that they are valid and correctly implemented on the user side.

Second entry is my secondary organization which has it's own email domain listed as it's only SMTP email policy. These all seem to work fine.

Lowest priority is the default policy which also has the same email domain as the highest priority policy (my main domain that is having the problem) as it's only SMTP email. I'm not sure why that is like that (I didn't build this server so I'm not 100% certain why that is listed as such) but that the fact that SOME email to the main domain gets through led me to believe that the policy was not likely to be the problem, I would have expected that all addresses would fail if it was a recipient policy issue.

Is that an incorrect assumption?


Sounds reasonable enough.
quote:



As for making it authoritative I'm not sure exactly what you mean but both the top 2 priority SMTP policy have the "This Exchange organization is responsible for all mail delivery to this address" option checked.


Isn't the Default Recipient Policy marked as Authoritative?
quote:



I'm not sure what else you might be referring to but again I would think all mail would fail if that was not set correctly, perhaps that is an incorrect assumption as well?

It almost seems as though some of my email addresses are either on some sort of blacklist in Exchange or are missing from some sort of whitelist but to my knowledge neither of those exist. Is there some sort of address book that needs to be edited that I am completely missing?

Thanks again for your help.

Steve


Take a look into your SMTP logfiles and check to see if it complains about something when receiving a SMTP connection sending email to one of the recipients you are having problems with.

Logging the SMTP Service

(in reply to sprinsen)
Post #: 4
RE: Some external email rejecting to valid recipients - 25.Oct.2010 12:43:26 PM   
sprinsen

 

Posts: 3
Joined: 23.Oct.2010
Status: offline
OK, the default policy is marked Authoritative but it's grayed out so I couldn't change it anyway, I meant to write that but got off track.

In any case I've figured out the problem.

It's really kind of stupid of me to have not thought of it before but your advise put me on the right path to to "eureka!" moment.  It was our SPAM filter causing the problem.  Somewhere along the way the guy who used to admin the filter enabled the inbound whitelist feature.  I was not aware that was happening so I never checked the filter. We don't add a lot of new users to that domain that get email so it's been some time since we needed to update the list.

Once I started checking the Exchange logs I realized that the rejected emails were never even hitting our Exchange server which made me take a step backward and check the SPAM filter and found the list.

Thanks for your help, you actually did put me on the path to finding the problem even though it was not an Exchange issue.  Sometimes I just need to bounce a problem off someone else to break the mental logjam and see the bigger picture.

Steve

(in reply to sprinsen)
Post #: 5
RE: Some external email rejecting to valid recipients - 26.Oct.2010 4:24:24 AM   
Jesper Bernle

 

Posts: 912
Joined: 15.Oct.2007
Status: offline
quote:

ORIGINAL: sprinsen

Thanks for your help, you actually did put me on the path to finding the problem even though it was not an Exchange issue. Sometimes I just need to bounce a problem off someone else to break the mental logjam and see the bigger picture.

Steve


You're welcome Steve. By the way it's the same with me. Sometimes we need 4 eyes instead of 2.

(in reply to sprinsen)
Post #: 6

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