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internal app can't send email to office 365

Posted on 2013-06-28
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Last Modified: 2013-07-06
After we migrated to Online Exchange, our internal database not able to send email . I found out Office 365 use SSL/TLS with port 587, and our database only accept SSL port 465. I added in the Yahoo email and server then the database work fine, but not Office 365. I created smtp relay on the server, but still doesn't work. We have sbs 2011 standard server. Please help, thanks.
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Question by:ld952
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Expert Comment

by:ecarbone
ID: 39285632
I don't think Microsoft has any plans of changing this, and as far as I can tell, you cannot change the port that hosted Exchange / Office 365 uses.

Your best bet (if you can't change the way your database app works) is to set up a relay server.

You mentioned you did that, and it didn't work. Can you provide more detail?

What exactly doesn't "work"?
Are you able to telnet into the SMTP relay and test it?
Is it not accepting connections? Or it accepts the connection but won't relay it?
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Expert Comment

by:nate0187
ID: 39285660
Why can't you change the port in the app?
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by:ld952
ID: 39285676
I just run telnet on my domain and it failed on all 3 ports 25, 465, and 587. It could be that I setup properly but don't know how to connect it with the app. I'll setup the smtp relay again. Right now I follow this link to re-setup the smtp relay (http://support.microsoft.com/kb/230235). If you have any a better link, please advise.

The internal app we had is a DBA database, and I already contacted the tech support. He said the app only take SSL port 465 for email setting. I test office 365 smtp setting with scan to email on printer and it worked fine. I'll reconfigure the smtp relay again let you guy know, really appreciate your help.
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ld952 earned 0 total points
ID: 39290417
:) . I am able to setup SMTP relay by using this guide "Setup Windows Server 2008 SMTP Relay for Office 365" (http://www.getoffice365trial.com/configure-office-365-smtp-relay/).

This is what I think how SMTP route (please correct me if I am wrong)

LOB app > virtual smtp > office 365

How I setup SMTP relay for SBS 2011 standard.

1/ Create virtual smtp in IIS. Setup TLS/SSL if your LOB app require otherwise you don't have to.
Setting for each tab in Properties
General: add proper TCP port that work with your LOB app (ect: 25, or 465), logging is optional
Access: authentication > none, secure communication > none, connection and relay > all except the list below
Messages: I changed limit messages size to 10,000 KB
Delivery:  Outbound security > basic authentication > add user's email and password with TLS encryption checked, outbound connection > tcp port > 587, advanced > add smart host which for me is smtp.office365.com and unchecked "Attempt..." and "Perform...", LDAP routing > none, security > none
LDAP Routing
Security

2/ Create new remote domain (which is for office365) by right click on domain > new > remote
General: I didn't check on "Allow..." and "Send HELO..", outbound security > basic authentication > fill in user's email and address and check TLS, route domain > forward all mail to small host > smtp.office365.com
Advanced: none

3/ Make sure you point your LOB app to the virtual smtp (FQDN): right click on virtual server that you created > properties > Delivery > Advanced > fully-qualified domain name:

Hope my quick guide can help other :).
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Author Comment

by:ld952
ID: 39290928
Ok
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Author Comment

by:ld952
ID: 39294667
Ok
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Author Closing Comment

by:ld952
ID: 39303703
I did more research and understood how the smtp relay work and worked from there
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