Hi,
I hope I'm posting this in the correct area. I apologize in advance as this is lengthy.
I have a windows server 2008 running an IIS smtp relay. Our web portal uses this relay to send email out to web-users of our portal. A portal user (external to our company) has said that they did NOT receive several emails generated from the website. There's a couple of things that I'm hoping to gain insight from here to help me solve this problem:
1. My website keeps track of when it submits an email to the relay....but nothing more (ie; no communication between web-site and relay to make sure messages are sent / not sent). Typically, the time that my website submits the email to the relay (found in my website logs) matches exactly to the time in the smtp log on the relay server C:\windows\system32\logfile\smtpsvc1\ex<date>.log...from there I can also see the email transmission details (time, mail from, rcpt to, data, etc). In this particular example, my web-site logs show that an email was generated from the website on 2015-04-08 @ 19:38:26.750. However, I don't see an email transmission in the smtp logs matching that time. In the smtp logs i see an email transmission to this person starting to this person in the smtp logs until 2015-04-08 @ 19:42:42 (5 mins later). Does anyone have an explanation for the delay? Is my server just busy? Again, i typically don't see this. It also doesn't help that the smtp log does not show the subject (or anything else) of the email that it's trying to delivery to help identify the email. Anyone know of any way to add something to the logs to identify the emai?
2. I'm seeing multiple RSET's in the transmission to this person....all of them come after the "DATA" and 250 response....to my knowledge the RSET commands after the "DATA" and 250 response will not cancel the email. I've even tested this with telnet and received the email that i sent followed by an RSET. however, i don't understand the two 250 responses after the RSET...can anyone shed light on this?IE:
MAIL - FROM:<xxxxxx>+SIZE=200982 0 0 4 0 9485 SMTP - - - -
250+Sender+<xxxxxxx>+OK 0 0 44 0 9517 SMTP - - - -
RCPT - TO:<xxxxxx> 0 0 4 0 9517 SMTP - - - -
250+Recipient+<xxxxxxxx>+OK 0 0 39 0 9563 SMTP - - - -
DATA - - 0 0 4 0 9563 SMTP - - - -
250+Ok:+queued+as+C67984F0AAE 0 0 29 0 9657 SMTP - - - -
RSET - - 0 0 4 0 9657 SMTP - - - -
250+Requested+mail+action+okay,+completed 0 0 41 0 9735 SMTP - - - -
250+Ok:+queued+as+D8C9C4F0AAC 0 0 29 0 9735 SMTP - - - -