Hi there!
I' looking for some help debugging a blocking error in our DEV environment.
We're currently using Windows 2008 R2 Standard, with IIS 7.5 and MS SQL Server 2012 Standard.
We're experiencing troubles while trying to use database mail in conjunction with Office365 SMTP.
We've generated our self-signed certificate, via IIS, and configured SMTP Virtual Relay Server with local (machine-name) and remote domain, following a step-by-step tutorial from configureoffice365.com.
We've also checked at the original MSDN tutorial, but it's been of little use (at least for us).
We would like to use our Office365 SMTP server to send out notifications and we're currently using Office365 working credentials to try the SMTP authentication, but we're stuck with this error (x is used to hide sensible data):
OutboundConnectionCommand [12/May/2014:13:35:08 +0100] "STARTTLS - SMTP" 0 8
OutboundConnectionResponse [12/May/2014:13:35:08 +0100] "- -?220 2.0.0 SMTP server ready SMTP" 0 27
OutboundConnectionCommand [12/May/2014:13:35:08 +0100] "EHLO -?SQLDEVxxxxx SMTP" 0 4
OutboundConnectionResponse [12/May/2014:13:35:08 +0100] "- -?250-xxxxx.outlook.office365.com Hello [x.x.x.x] SMTP" 0 58
OutboundConnectionCommand [12/May/2014:13:35:08 +0100] "AUTH - SMTP" 0 4
OutboundConnectionResponse [12/May/2014:13:35:08 +0100] "- -?334 xxxxx SMTP" 0 16
OutboundConnectionResponse [12/May/2014:13:35:14 +0100] "- -?535 5.7.3
Authentication unsuccessful SMTP" 0 37
Any idea or suggestion?
Thank you.