We have a web application that is configured to use an internal mail relay running on Windows Server 2012 R2, IIS 6.0 for the SMTP though. I just put this server in place as a replacement for an old 2003 server that was doing the same function. I configured both the same so far as I can tell I did a side by side compare.
Our web application allows the user to enter their Email address in the from field so that if the Email bounces it should go back to that user so they know they entered a bad Email address. This previously worked from what I was told and does not work now.
I looked at the queue and badmail folder and couldn't find anything. The logs look fine, this one is going to Office 365. I tried Emailing the user from my Outlook and I do get the NDR so for some reason Office 365 doesn't want to send an NDR from the Email created through our application.
2016-01-29 20:29:29 192.168.168.167 l3nexproc05 SMTPSVC1 SMTPSERVER 192.168.168.168 0 MAIL - +FROM:<ouruser@domain.com> 250 0 44 31 16 SMTP - - - -
2016-01-29 20:29:29 192.168.168.167 l3nexproc05 SMTPSVC1 SMTPSERVER 192.168.168.168 0 RCPT - +TO:<badaddress@domain.com> 250 0 38 35 0 SMTP - - - -
2016-01-29 20:29:29 192.168.168.167 l3nexproc05 SMTPSVC1 SMTPSERVER 192.168.168.168 0 DATA - <SMTPSERVERcncTU4DYo000029e2@oursubdomain.domain.com> 250 0 132 4748 0 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 220+BL2FFO11FD024.mail.protection.outlook.com+Microsoft+ESMTP+MAIL+Service+ready+at+Fri,+29+Jan+2016+20:29:37++0000 0 0 115 0 62 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 EHLO - oursubdomain.domain.com 0 0 4 0 62 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 250-BL2FFO11FD024.mail.protection.outlook.com+Hello+[4.53.177.34] 0 0 65 0 187 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 MAIL - FROM:<ouruser@domain.com>+SIZE=5069 0 0 4 0 187 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 250+2.1.0+Sender+OK 0 0 19 0 265 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 RCPT - TO:<badaddress@domain.com> 0 0 4 0 265 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 250+2.1.5+Recipient+OK 0 0 22 0 375 SMTP - - - -
2016-01-29 20:29:29 7.8.9.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 BDAT - 5069+LAST 0 0 4 0 375 SMTP - - - -
2016-01-29 20:29:31 7.8.9.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 250+2.6.0+<SMTPSERVERcncTU4DYo000029e2@oursubdomain.domain.com>+[InternalId=24597277712205,+Hostname=DM3PR11MB1019.namprd11.prod.outlook.com]+10759+bytes+in+0.290,+36.191+KB/sec+Queued+mail+for+delivery 0 0 198 0 1968 SMTP - - - -
2016-01-29 20:29:31 7.8.9.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 QUIT - - 0 0 4 0 1968 SMTP - - - -
2016-01-29 20:29:31 7.8.9.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 221+2.0.0+Service+closing+transmission+channel 0 0 46 0 2047 SMTP - - - -
2016-01-29 20:29:33 1.2.3.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 250+Accepted 0 0 12 0 84406 SMTP - - - -
2016-01-29 20:29:33 1.2.3.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 DATA - - 0 0 4 0 84406 SMTP - - - -
2016-01-29 20:29:33 1.2.3.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 354+Enter+message,+ending+with+"."+on+a+line+by+itself 0 0 54 0 84469 SMTP - - - -
2016-01-29 20:29:35 1.2.3.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 250+OK+id=1aPFfq-0002Lp-51 0 0 26 0 85594 SMTP - - - -
2016-01-29 20:29:35 1.2.3.4 OutboundConnectionCommand SMTPSVC1 SMTPSERVER - 25 QUIT - - 0 0 4 0 85594 SMTP - - - -
2016-01-29 20:29:35 1.2.3.4 OutboundConnectionResponse SMTPSVC1 SMTPSERVER - 25 - - 221+host2.52601.com+closing+connection 0 0 38 0 85656 SMTP - - - -
