Exchange trying to use Internal Server to send to external Email address
Our Exchange Server is working fine: both internal & external Email being sent & recieved OK. However, there is one Email that refuses to go: jill@external.com. I can tell by looking at the queues that other external Emails all go to an external ServerHostname, eg, Google emails go to gmail-smtp-in.l.google.com, etc. But this one Email always tries to use our Exchange Server to send through, ie, ServerHostname = mycompany-exchange and not, eg, smtp.gmail.com or mx3.hotmail.com. If the user tries to use her personal Email or I send from my personal email (eg, through Gmail), then the recipient gets it OK, so it's not a problem with the Recipient not getting mail--it's a problem with our Exchange thinking that it has to use itself instead of an External Server to relay the mail. Do I need to set-up a Connector or add something to our DNS to tell Exchange to route this externally? If so, could someone please advise how I would do this, as I wouldn't be familir with such. many thanks for any help you can provide. Brian Live Long and Prosper
August 23rd, 2010 8:17pm

The first things that come to mind is that for some reason, your Exchange seems to feel the address/domain is one it's authoritative for. Possibly the domain is listed on another internal system or send connector? how I would trouble shoot this would be to do message tracking, and also increase logging levels. Ideally once you establish the domains your Exchange is responsible for, and configure any send connectors to internal domains, It will choose how best to get a message to that domain. If it's NOT internal, it will simply send it out to the internet (route of last resort). Last thought would be if you have a contact set up with this email address, that maybe pointing to an internal address? Verify that address isn't located in any contacts. Good Luck!
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August 23rd, 2010 9:23pm

I ran into a similar situation recently, and the cause turned out to be that the sender had somehow set up the recipient's address in their Outlook 2003 Contacts as something other than SMTP. Changing it to SMTP fixed the problem. -Peter
August 24th, 2010 2:25am

Thank you both for your replies. Peter, this happens from my Outlook too, and I don't have jill@external.com set-up as a Contact, so--unfortunately--I can't change the "E-mail Type", ie, SMTP. I assume this means it's not a contact issue (ie, a Contact set-up incorrectly on another user's Outlook shouldn't affect the way an Email from my Account gets routed? Dan, we have only 1 Exchange Server, and this has only 1 Send Connector with the following details: General: Protocol logging level: None Address Space: SMTP Address: * Cost: 1 Network: Use domain name system (DNS) "MX" records to route mail automatically Source Server: MY-EXCHANGE: Site: Belfast: Role: Mailbox, Client Access, Hub Transport It was the message tracking Tool that helped me idetify that this was trying to go through our Exchange. Is there something else in Message Tracking that I should be searching for? Many thanks for your ongoing help. Brian Live Long and Prosper
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August 25th, 2010 3:57pm

Hi, To troubleshoot the issue, I suggest you access the link below to obtain the MX record of the problematic email, and then use telnet to send email to the target email address for a test. NsLookup Tool link Note: You should type the external domain name for the problematic email address. To send email via Telnet, please refer to the following article: Telnet to Port 25 to Test SMTP Communication If the email cannot be sent to the target address via Telnet, please let me know. Otherwise, please open Queue Viewer and check which procedure does the email hang, at Submission, Categorizer or Remote Deliver? Also, please check protocol log, you can got records of outside email, the log is under path of \Program Files\Microsoft\Exchange Server\TransportRoles\Logs\ProtocolLog\smtpsend\ Thanks. Novak Wu-MSFT
August 26th, 2010 11:42am

Thanks for your reply Novak. I looked up the Server on the NsLookup Link, and got the following information: server:ns57.domaincontrol.com MX preference: 0 exchange: smtp.europe.secureserver.net MX preference: 10 exchange: mailstore1.europe.secureserver.net 188.121.58.1 I opened a Command Prompt and tried all those listed below, but each failed. Have I typed the wrong thing? Many thanks Brian telnet 188.121.58.1 25 (Connect Failed) telnet refoundonline.com 25 (Could not open connection to host on Port 25. Connect Failed) telnet ns57.domaincontrol.com 25 (Connect Failed) telnet smtp.europe.secureserver.net 25 (554-n1pismtp01-001.prod.ams1.secureserver.net 554 Your access to this mail system has been rejected due to spam or virus content). telnet mailstore1.europe.secureserver.net 25 (Connection to Host Lost)Live Long and Prosper
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August 26th, 2010 5:46pm

Hi, Since the remote server cannot be connected via Telnet command, it can occur by network connection. At this stage, I suggest you temporarily turn off firewall and anti-spam, and then use the command again. If the issue persists, you may need contact the administrator of the remote domain to consult the detail MX name and run a test again. Thanks. Novak Wu-MSFT
August 27th, 2010 4:49am

Thanks Novak I would be reluctant to turn off our Watchguard Firewall, and seeing as this is the only Domain that we're having trouble sending to, I thought maybe it was a DNS or Send Connector issue. Is there a way that I can force it past Exchange via a Connector etc without having to restored to turning off the Firewall or Anti-Spam program? Many thanks Brian Live Long and Prosper
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August 30th, 2010 7:03pm

Since other emails can be sent out to external domains, the issue may not be related to DNS or Send Connector. If DNS or Send Connector is not configured correctly, all emails will not be sent out to external. To bypass Exchange server, we have to use telnet command to connect the remote domain. You can temporarily disable firewall and anti-spam and run the command again. When the test is completed, you can enable them at once. If still failed, it’s highly recommended to contact the administrator of the remote domain and confirm whether the MX record is correct. Meanwhile, I suggest you refer to the following article to configure Message Tracking and collect SMTP log file for research. Configure Message Tracking Hope this helps. Novak Wu-MSFT
August 31st, 2010 4:39am

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