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Why can I not send emails to a distribution group I have just created?

Posted on 2009-05-04
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Last Modified: 2013-11-30
I can send emails to any other address ini this domain but i have just created a new distribution group which, when I send an external email to I get the error:

The following recipient(s) could not be reached:

  There was a SMTP communication problem with the recipient's email server. Please contact your system administrator.
  <#5.5.0 smtp;550 Invalid recipient <> (#5.1.1)>

What puzzles me is why this only happens on new distribution groups?  The exhange server is not set to do a reverse DNS lookp and the distribution group works internaly.  It may be worth mentioning that exchange is behind ISA firewall.
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Question by:johnstuartcowell
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12 Comments
 
LVL 58

Expert Comment

by:tigermatt
ID: 24293706

When did you create the group? If you try to send mail to it too quickly after creating it, Exchange will not have internally updated and will therefore not recognise the group and its new email address exists yet.

-Matt
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LVL 4

Expert Comment

by:anvanster
ID: 24293712
Hi,
Any anti spam engines on your network? like BrightMail, PineApp?
This reject can be from anti spam server, which is not synchronized yet with your Exchange server. Synchronization usually configured to once / twice a day.
Do you have problems sending to this group from inside the network?
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LVL 57

Expert Comment

by:Pete Long
ID: 24293787
Hello johnstuartcowell,

On the properties for the group untick "require authentication"

Regards,

PeteLong
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LVL 57

Expert Comment

by:Pete Long
ID: 24293807
anvanster,
When you create any distribution list with Exchange Management Console - EMC or Exchange management Shell - EMS in 2007 by default Sender Authentication is Enabled to prevent unwanted messages from spam and from outside domain, this is by default in design...

 

You need to disable it to get email from outside.

 

From EMC: Recipient Configuration -> Distribution Groups -> Select a group -> Properties -> Mail Flow Settings -> Message Delivery Restrictions -> Properties -> Untick ?Require that all senders are authenticated?
http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/56e342e4-1aed-4164-a7b9-0e5fabf102f0


PeteLong
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Author Comment

by:johnstuartcowell
ID: 24294170
Thank you all for your responses.

Tigermatt, The email group was set up 24 a couple of days ago now, I left it to ake sure that I had given enough time to let the change go through.

PeteLong, I have Exchange 2003, does your posts relate to this or just Exchange 2007?

Anvanster, the emails go through Star's Messagelab service.  Do I need to make a change with Star?

Phil
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LVL 4

Expert Comment

by:anvanster
ID: 24294232
When you are inside:
In outlook: do you see this group in address book?
   Can you send mail to this group?

I'm not familiar with star's service, but there should be an option for synchronizing Active Directory/LDAP addresses.  
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LVL 58

Expert Comment

by:tigermatt
ID: 24294423

I too am not familiar with MessageLabs, but I would not have thought you have to replicate your internal email address database with their servers. That would be plain stupid and I certainly wouldn't buy into the product if that was the case.

What do the NDR reports list as being the generating server? Does the NDR come from your server or from MessageLabs'?

-Matt
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Author Comment

by:johnstuartcowell
ID: 24294500
Anvanster, THe email group does show up internaly and I can send internal emails to the group.

Tigermatt, The NDR report is generated by the server sending the email.
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LVL 58

Accepted Solution

by:
tigermatt earned 84 total points
ID: 24294578

What happens if you send an email internally to the group using its SMTP email address (rather than picking the group from the GAL)? Does that work?

If that works, the problem must lie with MessageLabs, since that would prove your server knows the group exists and can receive email.

It would also be worth checking the Email Addresses tab on the group on the server to verify the email address is not different to what you expect, like having a '2' after it for instance.

-Matt
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LVL 65

Assisted Solution

by:Mestha
Mestha earned 83 total points
ID: 24294871
The fact that the NDR is generated by the server sending the email shows that the problem is with Message Labs. They are rejecting the message, most likely because they are doing some kind of recipient validation. If the message was being rejected by your server then message labs server would be in the NDR.

Simon.
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LVL 4

Assisted Solution

by:anvanster
anvanster earned 83 total points
ID: 24301937
MessageLabs has synchronization with AD according to their FAQ. Otherwise the service is not worth much if all mail to nonexistent recipients can reach your exchange server, and they get paid by number of users, like CAL in exchange.
Go to: http://images.messagelabs.com/help/en-us/default.htm
It's online help about  MessageLabs services. E-mail Services --> E-mail Anti Spam --> Email address registration... You have to register your new group address in MessageLabs and then activate it. Look in Email address activation.

Hope this helps
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