Relay mail using SBS2003/Exchange 2003 to Office 365

Posted on 2011-09-13
Medium Priority
Last Modified: 2012-05-12

Got a little issue.
My Company switched to Office 365 recently.
Now i want (need) our local sbs2003 server to relay mail for some things (UPS, backup status, scan to mail) to the office 365 smtp server.
I configured the default SMTP virtual server on sbs2003 to use a smarthost (podxxxxxx.outlook.com). using TLS and TCP port 587.
I also created a routing group that forwards all mail to the same podxxxxxxx.outlook.com. (tried with an adres space of * and with individual domains).  Also configurred outbound security and enabled TLS.

When i try a test mail i get no error. It's never received either.
The exchange message tracking says the mail is routed and queued for remote delivery.

Anyone who has a clue what i'm missing/doing wrong?
Any help appreciated.
Question by:JHagman
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LVL 12

Expert Comment

ID: 36535048
check in the Queue under Exchange --> <Server name> --> Queues and see if the message is stuck there - if it is, click on it to see more details at the bottom. Also check %systemroot%\logfiles\SMTPSVC1 for related errors.

Author Comment

ID: 36535145
Queue says it can't connect to remote smtp (the podxxxx.outlook.com) so there must be something wrong with the settings (i asume).
The queue error on the smtp connector: The remote server did not respond to a connection attempt.

The logfile shows no errors.

So it's either my config for authentication or the podxxxxx is rejecting connections.

LVL 12

Accepted Solution

marcustech earned 750 total points
ID: 36535157
Check if podxxxx.outlook.com is accepting connections on port 587 ("telnet podxxxx.outlook.xom 587" from command line) - you won't actually be able to test smtp but can at least see if the server accepts the connection. If it accepts the connection (screen will go blank) then there's probably something up with your authentication settings, if not there's either a port blocked by a firewall somewhere or the server name is wrong.

Author Closing Comment

ID: 37070579
Since it's still not working here, i'll close the question.
We found another "workaround".
LVL 12

Expert Comment

ID: 37073418
If it's still not working and you would like it to work, rather than closing the question you could respond and let us know what the result of your telnet test is.  Then we can advise further troubleshooting steps and hopefully resolve your issue.  Thanks for accepting the answer though.

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