Cannot get db mail to work via SMTP Relay for Office 365 in SQL Server 2014 on Windows Server 2012 R2

Question

Our company recently moved to Office 365 which mean our on premise exchange server went away as well with the move.  I am trying to configure my new sql server (OS-Windows Server 2012 R2, DBMS- SQL 2014 Std Edtion).  After some searching I found
this article (http://blogs.technet.com/b/meamcs/archive/2013/02/25/how-to-configure-sql-database-mail-so-send-emails-using-office-365-exchange-online-a-walkthrough.aspx) and have followed these steps exactly, but to no avail.  I did some further research
on the SMTP relay I setup and found a way to test it (listed here http://technet.microsoft.com/en-us/library/dn592151(v=exchg.150).aspx at the bottom of the article).  If I drop the email.txt file in the pickup folder, it gets sent out no problem.
 I have configured my db email exactly as describe here(http://blogs.technet.com/b/meamcs/archive/2013/02/25/how-to-configure-sql-database-mail-so-send-emails-using-office-365-exchange-online-a-walkthrough.aspx).  But keep getting an unable to connect
to SMTP server error.  I have even tried completely shutting down firewall to see if that is the issue and multiple restarts.  Any ideas how to get this to work on Office 365?
DB Mail error log:
Date 6/10/2014 10:28:41 PM
Log Database Mail (Database Mail Log)
Log ID 46
Process ID 2196
Mail Item ID 19
Last Modified 6/10/2014 10:28:41 PM
Last Modified By xx
Message
The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 2 (2014-06-10T22:28:41). Exception Message: Cannot send mails to mail server. (Failure sending mail.).

Answer 1

Hi,
I followed this blog and got the below error message in the Database Mail Log.
“The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 2 (2014-06-11T19:34:00). Exception Message: Cannot send mails to mail server. (Mailbox unavailable. The server response was: 5.7.1 Unable to relay
for [email protected]).”
If you are getting the same error message, you can try the below steps to resolve the issue.
1. Open the IIS 6.0 management console. Right click on the SMTP server and open the properties window.
2. Click on the Access tab, click Relay button under Relay restrictions. loopback IP address (i.e 127.0.0.1).
Then the email should be sent out from Database Mail without problem.
Thanks.
Tracy Cai
TechNet Community Support