I had one complaint of an email that was sent from Smartermail and bounced and that started me looking at the delivery log and I found several instances of this over the past month.

 

The user gets authenticated, but as "undefined" via the actual email address.  Here's a chunk of the log file that shows the user mycustomer is authenticated, but the mail from is "undefined" and gets rejected.  It's only happened about 8 times to 5 users over a month.  This shows an Outlook/Office 365 server rejecting it, but it doesn't matter if it's sent to Yahoo, Comcast, Google - I have examples of each.

 

[2018.04.02] 15:05:32 [65477] Delivery started for undefined (via mycustomer@sendingdomain.com) at 3:05:32 PM
[2018.04.02] 15:05:48 [65477] Starting Spam Checks.
[2018.04.02] 15:05:48 [65477] Skipping spam checks: User authenticated
[2018.04.02] 15:05:48 [65477] Spam Checks completed.
[2018.04.02] 15:05:50 [65477] Sending remote mail for undefined
[2018.04.02] 15:05:51 [65477] Sending remote mail to: recipient@receivingdomain.com
[2018.04.02] 15:05:51 [65477] Initiating connection to xxx.xxx.xxx.xxx
[2018.04.02] 15:05:51 [65477] Connecting to xxx.xxx.xxx.xxx (Id: 1)
[2018.04.02] 15:05:51 [65477] Connection to xxx.xxx.xxx.xxx from xxx.xxx.xxx.xxx succeeded (Id: 1)
[2018.04.02] 15:05:51 [65477] RSP: 220 BL2NAM02FT034.mail.protection.outlook.com Microsoft ESMTP MAIL Service ready at Mon, 2 Apr 2018 19:05:50 +0000
[2018.04.02] 15:05:51 [65477] CMD: EHLO mail.gds.us
[2018.04.02] 15:05:51 [65477] RSP: 250-BL2NAM02FT034.mail.protection.outlook.com Hello [209.235.198.83]
[2018.04.02] 15:05:51 [65477] RSP: 250-SIZE 157286400
[2018.04.02] 15:05:51 [65477] RSP: 250-PIPELINING
[2018.04.02] 15:05:51 [65477] RSP: 250-DSN
[2018.04.02] 15:05:51 [65477] RSP: 250-ENHANCEDSTATUSCODES
[2018.04.02] 15:05:51 [65477] RSP: 250-STARTTLS
[2018.04.02] 15:05:51 [65477] RSP: 250-8BITMIME
[2018.04.02] 15:05:51 [65477] RSP: 250-BINARYMIME
[2018.04.02] 15:05:51 [65477] RSP: 250-CHUNKING
[2018.04.02] 15:05:51 [65477] RSP: 250 SMTPUTF8
[2018.04.02] 15:05:51 [65477] CMD: STARTTLS
[2018.04.02] 15:05:51 [65477] RSP: 220 2.0.0 SMTP server ready
[2018.04.02] 15:05:51 [65477] CMD: EHLO mail.gds.us
[2018.04.02] 15:05:51 [65477] RSP: 250-BL2NAM02FT034.mail.protection.outlook.com Hello [209.235.198.83]
[2018.04.02] 15:05:51 [65477] RSP: 250-SIZE 157286400
[2018.04.02] 15:05:51 [65477] RSP: 250-PIPELINING
[2018.04.02] 15:05:51 [65477] RSP: 250-DSN
[2018.04.02] 15:05:51 [65477] RSP: 250-ENHANCEDSTATUSCODES
[2018.04.02] 15:05:51 [65477] RSP: 250-8BITMIME
[2018.04.02] 15:05:51 [65477] RSP: 250-BINARYMIME
[2018.04.02] 15:05:51 [65477] RSP: 250-CHUNKING
[2018.04.02] 15:05:51 [65477] RSP: 250 SMTPUTF8
[2018.04.02] 15:05:51 [65477] CMD: MAIL FROM:<undefined> SIZE=116285
[2018.04.02] 15:05:51 [65477] RSP: 501 5.1.7 Invalid address [BL2NAM02FT034.eop-nam02.prod.protection.outlook.com]
[2018.04.02] 15:05:51 [65477] CMD: QUIT

 

This only started happening in March after I upgraded to SM 16.3.6649.  Has anyone else seen this?

 

Thanks,
Jane