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Troubleshooting SMTP Relay to external addresses on Exchange 2010

Posted on 2014-04-01
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Last Modified: 2014-06-13
Our Payroll server once a month sends emails to all staff with their Pay Advice. Up until now, this was only to internal Addresses.

Now there is the requirement to send to external addresses. However none appear to reach the external recipients. All internal emails are received without issue.

Email Server = Exchange 2010 (Win Svr 2008 R2)
Payroll Server = Win Svr 2008 R2

The Payroll Application does not have a mailbox attached to it. The Exchange Server address, SMTP port & the sender address are configured in the SMTP settings. (so the payroll app is not connected to a mailbox, it is just sending using an alias). The Sender address is just our Payroll officers email address.

I know that with this setup, you need to ensure the Payroll Server IP address is added to the SMTP Relay senders list for the Payroll server to be able to send internally, but how can I configure Exchange 2010 to make it send externally also? Is it possible?

I am unable to use the Exchange mail flow tools as the emails are not stored in any mailbox.
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Question by:Howzatt
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7 Comments
 
LVL 6

Assisted Solution

by:rick81
rick81 earned 200 total points
ID: 39971589
what payroll software are you using?
if you have setup the relay correctly then the payroll machine should be able to send externally.  
are you using smtp authentication within the payroll software at all?  usually it will ask for a smtp mail server address and to auth or not.  if you put in an account details it should send ok.  another thing you could try is setting the outgoing mail sever to your ISP mail server.  in most cases this doesnt need smtp auth and will send externally.
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LVL 12

Assisted Solution

by:Vaseem Mohammed
Vaseem Mohammed earned 100 total points
ID: 39971605
My suggestion will be to use a dedicated account for the application, and use SMTP authentication. In this way you don't need to setup relay.
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LVL 63

Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 200 total points
ID: 39971854
You just need to setup an Application Relay receive connector.
http://semb.ee/apprelay

Lock it down to the specific address the software runs on.

Simon.
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Author Comment

by:Howzatt
ID: 39973893
So I added the appropriate IP address of the Payroll server to the Relay connector. We already had one, but the IP for the payroll server was missing.

I have asked payroll to test to my yahoo address and it worked.

I then asked Payroll to resend the emails that previously failed. Only some of the recipients have received them. Half of them have not. One of them also has a Yahoo address.

Just wondering how I can track the messages if the Payroll software does not have a Mailbox attached to it?
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LVL 6

Assisted Solution

by:rick81
rick81 earned 200 total points
ID: 39973911
setup logging on the relay and then try and send the emails again, then review the log.

http://exchangeserverpro.com/exchange-server-protocol-logging/
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LVL 63

Accepted Solution

by:
Simon Butler (Sembee) earned 200 total points
ID: 39975252
If the message went to some of the users and not others then it is probably not the relay at fault - more likely the messages got flagged as spam.

Simon.
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Author Comment

by:Howzatt
ID: 40012858
Sorry have been on holidays. Have not had a chance to troubleshoot as yet. Will update tomorrow
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