We had an issue pop up recently and I'm completely stumped as to what the problem might be. We have Exchange 2003. All of a sudden not every email reaches us that is sent. Probably 90% of emails are received. Nothing has changed on the server but it does seem that most of the senders reside on large ISPs (road runner, etc...). However when they call at a later date to report we never got back to them, and they resend their email, we generally DO get that one. So it's not like the emails are blocked. Neither party receives a bounce error. I ran the Exchange Troubleshooting Assistant and Best Practices Analyzer Tool but to my knowledge there was nothing that stuck out as being an issue (although I may not be looking at the right thing). I now have the SMTP protocol logged on an hourly basis to try and troubleshoot. I checked reverse DNS and that we weren't a relay server and both checked out ok. Is there anything I am overlooking or has anyone experienced this issue before?

Does the SMTP logging show that you received the messages?

Ok, I just got one that didn't get through. Here's the log from the SMTP log. I changed the email addresses. sending@gmail.com was the sending email address and receiving@mydomain.com is my email address. 2010-08-24 15:09:55 64.18.0.35 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 MAIL - +FROM:<sending@gmail.com> 250 0 41 28 0 SMTP - - - - 2010-08-24 15:09:55 64.18.0.35 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 RCPT - +TO:<receiving@mydomain.com> 250 0 0 37 0 SMTP - - - - 2010-08-24 15:09:55 64.18.0.35 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 QUIT - psmtp.com 240 688 67 4 0 SMTP - - - - Yet, I never recieved it in my Outlook. Restarted outlook as well. Also, doesn't show up in journal account.

That was it? No DATA command? Sure you havent left off some of that SMTP conversation? If that is it, then your server is never accepting the message.

Here's two emails I sent at the same time. The email on top (from gmail) didn't get through. The email on bottom (from another domain) did. As you mentioned the gmail does not have the DATA command. Is there a way to rectify this? I assume this might be the issue. BTW. I can send email from that gmail account to other places, just not our exchange server apparently. Thank you so much for your help. 2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 HELO - +psmtp.com 250 0 38 14 0 SMTP - - - - 2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 MAIL - +FROM:<sending@gmail.com> 250 0 41 28 0 SMTP - - - - 2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 RCPT - +TO:<receiving@mydomain.com> 250 0 0 37 0 SMTP - - - - 2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 QUIT - psmtp.com 240 781 62 4 0 SMTP - - - - ---------------------------------- 2010-08-24 16:21:10 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 HELO - +psmtp.com 250 0 38 14 0 SMTP - - - - 2010-08-24 16:21:10 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 MAIL - +FROM:<receiving@myotherdomain.com> 250 0 43 30 0 SMTP - - - - 2010-08-24 16:21:10 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 RCPT - +TO:<receiving@mydomain.com> 250 0 0 37 0 SMTP - - - - 2010-08-24 16:21:12 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 DATA - +<513623640.248778.1282666868064.JavaMail.mail@webmail08> 250 0 140 1419 609 SMTP - - - - 2010-08-24 16:21:12 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 QUIT - psmtp.com 240 1844 62 4 0 SMTP - - - -

It really seems to be isolated to specific domains (a very select few), if that helps.

It looks like you're getting your email through Postini, so maybe a call to their tech support might be in order. -Peter

On Tue, 24 Aug 2010 16:29:02 +0000, repnescasb wrote: > > >Here's two emails I sent at the same time. The email on top (from gmail) didn't get through. Thaat's because no message was ever sent! You have HELO, MAIL FROM, RCPT TO, and QUIT. There's no DATA ot BDAT, thus no message. There's no long pause between any of the commands so it's not as if somethings timing out. The e-mail's coming from gmail.com through Postini, so you must be the Postini customer. It's time to ask them what their side of the conversation looks like. Do THEY show a DATA\BDAT in their logs? >The email on bottom (from another domain) did. That one's from Postini, too. Only that one has a DATA command. >As you mentioned the gmail does not have the DATA command. Is there a way to rectify this? I assume this might be the issue. You can't magically make it appear if it was never sent. Did the Postini server send one? >BTW. I can send email from that gmail account to other places, just not our exchange server apparently. That mail to other places doesn't pass through Postini. >Thank you so much for your help. > > > >2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 HELO - +psmtp.com 250 0 38 14 0 SMTP - - - - >2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 MAIL - +FROM:<sending@gmail.com> 250 0 41 28 0 SMTP - - - - >2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 RCPT - +TO:<receiving@mydomain.com> 250 0 0 37 0 SMTP - - - - >2010-08-24 16:20:48 64.18.0.93 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 QUIT - psmtp.com 240 781 62 4 0 SMTP - - - - > >---------------------------------- > >2010-08-24 16:21:10 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 HELO - +psmtp.com 250 0 38 14 0 SMTP - - - - >2010-08-24 16:21:10 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 MAIL - +FROM:<receiving@myotherdomain.com> 250 0 43 30 0 SMTP - - - - >2010-08-24 16:21:10 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 RCPT - +TO:<receiving@mydomain.com> 250 0 0 37 0 SMTP - - - - >2010-08-24 16:21:12 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 DATA - +<513623640.248778.1282666868064.JavaMail.mail@webmail08> 250 0 140 1419 609 SMTP - - - - >2010-08-24 16:21:12 64.18.0.39 psmtp.com SMTPSVC1 ADRSERVER 192.168.1.25 0 QUIT - psmtp.com 240 1844 62 4 0 SMTP - - - - --- Rich Matheisen MCSE+I, Exchange MVP --- Rich Matheisen MCSE+I, Exchange MVP

Hi repnescasb, For this issue, you can follow these steps below to troubleshoot the problem: 1. You should check whether the emails have been sent from Gmail server. If it is convenience, please check the smtp logs on Gmail server as well. 2. If the Gmail server have sent out the email, you can check the configuration on your firewall. 3. You can check whether there is a problem on Network. If the problem still exists, please don’t hesitate to let me know and I will be glad to be of assistance. Thank you, Tyler