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Alias email not being delivered

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Alias email not being delivered - 25.Apr.2012 1:18:20 PM   
forced

 

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In the EMC, I added an additional SMTP account to a user. If I email that alias internally, it gets delivered. When I use an outside email, the message does not get delivered. I don't get an error message back saying undelivered, however. I used https://www.testexchangeconnectivity.com to test the inbound SMTP Mail and I get a successfully delivered message. So it seems the mail hits the server, it just doesn't end up in the user's mailbox. I am on Exchange 2007 SP3 (Version: 08.03.0245.001)


Any thoughts?
-Steve
Post #: 1
RE: Alias email not being delivered - 25.Apr.2012 4:49:05 PM   
uemurad

 

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If the SMTP alias belongs to the same SMTP domain as the primary address, then confirm the association to the user object by typing the alias in the TO field in an Outlook message and Check Names. Does the name resolve to that user?

If the SMTP alias is part of a different SMTP domain, is it one that is already configured in Exchange to be authoritative? Do you have other addresses in that SMTP domain that work correctly?

Check the SMTP logs for the inbound tests. Is the inbound message received completely? Are all SMTP commands acknowledged with OK responses?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to forced)
Post #: 2
RE: Alias email not being delivered - 25.Apr.2012 6:41:50 PM   
forced

 

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quote:

ORIGINAL: uemurad

If the SMTP alias belongs to the same SMTP domain as the primary address, then confirm the association to the user object by typing the alias in the TO field in an Outlook message and Check Names. Does the name resolve to that user?

If the SMTP alias is part of a different SMTP domain, is it one that is already configured in Exchange to be authoritative? Do you have other addresses in that SMTP domain that work correctly?

Check the SMTP logs for the inbound tests. Is the inbound message received completely? Are all SMTP commands acknowledged with OK responses?

Same domain. my email is steve@mydomain.com and the alias is jobs@mydomain.com.

If I type "jobs" in the to field of a new message, the whole email address does not come up. When I hit Send, it does not come up with the correct suggestion email address.

In the SMTP log, this message does not have a RCPT TO command. Here is the end of it...
250 2.1.0 Sender OK,
<,RSET,
>,250 2.0.0 Resetting,
<,QUIT,
>,221 2.0.0 Service closing transmission channel,
Local

< Message edited by forced -- 25.Apr.2012 6:59:09 PM >

(in reply to uemurad)
Post #: 3
RE: Alias email not being delivered - 25.Apr.2012 8:45:50 PM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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quote:

If I type "jobs" in the to field of a new message, the whole email address does not come up. When I hit Send, it does not come up with the correct suggestion email address.
Type the entire address and click Check Names. Does it resolve correctly? If not, it means that AD doesn't see it as a valid alias and that's where your problem lies.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to forced)
Post #: 4
RE: Alias email not being delivered - 26.Apr.2012 10:49:39 AM   
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quote:

ORIGINAL: uemurad

quote:

If I type "jobs" in the to field of a new message, the whole email address does not come up. When I hit Send, it does not come up with the correct suggestion email address.
Type the entire address and click Check Names. Does it resolve correctly? If not, it means that AD doesn't see it as a valid alias and that's where your problem lies.


I typed in jobs@mydomain.com and hit check names, it resolved to my name.

(in reply to uemurad)
Post #: 5
RE: Alias email not being delivered - 26.Apr.2012 11:55:33 AM   
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OK, the jobs@mydomain.com email is now working. They are coming in and being delivered. Maybe this was a DNS replication issue?

However, the alias admin@mydomain.com still gives me the same RSET command. This isn't a big deal as it's not out there anywhere, but now I'm curious if this is a yahoo and gmail thing that would cause this to be reset or if it's internal. I've looked in our spam rules and there is nothing about "admin" in there.

(in reply to forced)
Post #: 6
RE: Alias email not being delivered - 26.Apr.2012 12:41:48 PM   
uemurad

 

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quote:

Maybe this was a DNS replication issue?
This wouldn't have anything to do with DNS. Perhaps you meant to say AD replication? If so, then that is a definite possibility.

How long did it take before "jobs" started working (from the time it was added)? Did you perform same name resolution tests on the "admin" address, and did you wait the same amount of time for it?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to forced)
Post #: 7
RE: Alias email not being delivered - 26.Apr.2012 12:54:58 PM   
forced

 

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quote:

ORIGINAL: uemurad

quote:

Maybe this was a DNS replication issue?
This wouldn't have anything to do with DNS. Perhaps you meant to say AD replication? If so, then that is a definite possibility.

How long did it take before "jobs" started working (from the time it was added)? Did you perform same name resolution tests on the "admin" address, and did you wait the same amount of time for it?


The "admin" was added about 30 mins after the "jobs" alias. Since the log shows RSET, it would seem that the sender (i tried yahoo and gmail) is cancelling the transmission?

(in reply to uemurad)
Post #: 8
RE: Alias email not being delivered - 26.Apr.2012 3:08:11 PM   
uemurad

 

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A successful SMTP transmission contains these commands (in order):

HELO/EHLO (depending upon the sending server using SMTP or ESMTP)
MAIL FROM (the sending address)
RCPT TO (the recipient address, one per command)
DATA/BDAT (the message)
QUIT

Which of these commands to you see in the failed transmissions, and what are the response codes (200-299 means OK)?

EDIT: You are correct - RSET is issued by the sending system to abort a transmission.

< Message edited by uemurad -- 26.Apr.2012 3:10:36 PM >


_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to forced)
Post #: 9
RE: Alias email not being delivered - 26.Apr.2012 3:39:59 PM   
forced

 

Posts: 8
Joined: 9.Nov.2011
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quote:

ORIGINAL: uemurad

A successful SMTP transmission contains these commands (in order):

HELO/EHLO (depending upon the sending server using SMTP or ESMTP)
MAIL FROM (the sending address)
RCPT TO (the recipient address, one per command)
DATA/BDAT (the message)
QUIT

Which of these commands to you see in the failed transmissions, and what are the response codes (200-299 means OK)?

EDIT: You are correct - RSET is issued by the sending system to abort a transmission.


Right after the MAIL FROM, i get a 250 2.1.0 Sender OK. The next line is:
RSET,
250 2.0.0 Resetting,
QUIT,
221 2.0.0 Service closing transmission channel

(in reply to uemurad)
Post #: 10
RE: Alias email not being delivered - 26.Apr.2012 3:56:43 PM   
uemurad

 

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The sending system is aborting the transmission. The question is why?

Are you sure there are no systems between the outside world and Exchange? For example, do you have a filter that has an approved recipient list?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to forced)
Post #: 11
RE: Alias email not being delivered - 26.Apr.2012 4:48:32 PM   
forced

 

Posts: 8
Joined: 9.Nov.2011
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quote:

ORIGINAL: uemurad

The sending system is aborting the transmission. The question is why?

Are you sure there are no systems between the outside world and Exchange? For example, do you have a filter that has an approved recipient list?


I can get emails to the "jobs" alias from the same yahoo and gmail accounts that I cannot get to the "admin" alias. We do have an email security appliance and there is no rules about an email coming in to the "admin" address.

(in reply to uemurad)
Post #: 12
RE: Alias email not being delivered - 26.Apr.2012 9:03:23 PM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
quote:

We do have an email security appliance and there is no rules about an email coming in to the "admin" address.
Are there any rules that say what to allow through? Typically recipient address filtering employs a whitelist. In other words, is there a list where "steve" and now "jobs" are included? If so, you now need to make sure that "admin" is also in that same list.

Also, since there's an appliance checking the mail first, you should see if that has SMTP logging capability and look for the transmission log there. Perhaps the appliance is rejecting one of the SMTP commands from yahoo or gmail.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to forced)
Post #: 13
RE: Alias email not being delivered - 27.Apr.2012 11:01:44 AM   
forced

 

Posts: 8
Joined: 9.Nov.2011
Status: offline
quote:

ORIGINAL: uemurad

quote:

We do have an email security appliance and there is no rules about an email coming in to the "admin" address.
Are there any rules that say what to allow through? Typically recipient address filtering employs a whitelist. In other words, is there a list where "steve" and now "jobs" are included? If so, you now need to make sure that "admin" is also in that same list.

Also, since there's an appliance checking the mail first, you should see if that has SMTP logging capability and look for the transmission log there. Perhaps the appliance is rejecting one of the SMTP commands from yahoo or gmail.


Well, I set about looking through every setting in the appliance. When I got to the "Spam Submissions" I got the answer. The "admin@mydomain.com" email was being used as a Probe account. So if an email was sent to that address, it would automatically be quarantined. This appliance was setup before I started, but now I am going to go through it bit by bit! Thanks for all the help!

-Steve

(in reply to uemurad)
Post #: 14

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