Thanks Michael.
When the emails are moving, the logs show this (I've edited to show only the gmail server and the message. I've xx'd out the cert info): 173.194.77.27:25,*,,attempting to connect 173.194.77.27:25,+,, 173.194.77.27:25,<,220 mx.google.com ESMTP kh3si24556964obc.53 - gsmtp, 173.194.77.27:25,>,EHLO CORP-EXCHANGE.wrightbg.com, 173.194.77.27:25,<,"250-mx.google.com at your service, [66.194.64.143]", 173.194.77.27:25,<,250-SIZE 35882577, 173.194.77.27:25,<,250-8BITMIME, 173.194.77.27:25,<,250-STARTTLS, 173.194.77.27:25,<,250-ENHANCEDSTATUSCODES, 173.194.77.27:25,<,250 PIPELINING, 173.194.77.27:25,>,STARTTLS, 173.194.77.27:25,<,220 2.0.0 Ready to start TLS, 173.194.77.27:25,*,,Sending certificate 173.194.77.27:25,*,"CN=<xxxxxxx> 173.194.77.27:25,*,"SERIALNUMBER=<xxxxxxxxx> 173.194.77.27:25,*,<xxxxxxxx>,Certificate serial number 173.194.77.27:25,*,<xxxxxxxxxx>,Certificate thumbprint 173.194.77.27:25,*,mail.wrightbg.com;www.mail.wrightbg.com;mail.wrightimg.com;autodiscover.wrightbg.com;autodiscover.wrightimg.com;corp-exchange.wrightbg.com,Certificate alternate names 173.194.77.27:25,*,,Received certificate 173.194.77.27:25,*,<xxxxxxxx>,Certificate thumbprint 173.194.77.27:25,>,EHLO CORP-EXCHANGE.wrightbg.com, 173.194.77.27:25,<,"250-mx.google.com at your service, [66.194.64.143]", 173.194.77.27:25,<,250-SIZE 35882577, 173.194.77.27:25,<,250-8BITMIME, 173.194.77.27:25,<,250-ENHANCEDSTATUSCODES, 173.194.77.27:25,<,250 PIPELINING, 173.194.77.27:25,*,3663171,sending message 173.194.77.27:25,>,MAIL FROM:<moni...@wrightbg.com> SIZE=1006, 173.194.77.27:25,>,RCPT TO:<wright...@gmail.com>, 173.194.77.27:25,<,250 2.1.0 OK kh3si24556964obc.53 - gsmtp, 173.194.77.27:25,<,250 2.1.5 OK kh3si24556964obc.53 - gsmtp, 173.194.77.27:25,>,DATA, 173.194.77.27:25,<,354 Go ahead kh3si24556964obc.53 - gsmtp, 173.194.77.27:25,<,250 2.0.0 OK 1363191423 kh3si24556964obc.53 - gsmtp, 173.194.77.27:25,>,QUIT, 173.194.77.27:25,<,221 2.0.0 closing connection kh3si24556964obc.53 - gsmtp, 173.194.77.27:25,-,,Local When they start failing I get this: 173.194.77.27:25,*,,attempting to connect 173.194.77.27:25,+,, 173.194.77.27:25,<,220 mx.google.com ESMTP ng7si6588885obb.147 - gsmtp, 173.194.77.27:25,>,EHLO CORP-EXCHANGE.wrightbg.com, 173.194.77.27:25,<,"250-mx.google.com at your service, [66.194.64.143]", 173.194.77.27:25,<,250-SIZE 35882577, 173.194.77.27:25,<,250-8BITMIME, 173.194.77.27:25,<,250-STARTTLS, 173.194.77.27:25,<,250-ENHANCEDSTATUSCODES, 173.194.77.27:25,<,250 PIPELINING, 173.194.77.27:25,>,STARTTLS, 173.194.77.27:25,<,220 2.0.0 Ready to start TLS, 173.194.77.27:25,*,,Sending certificate 173.194.77.27:25,*,"CN=<xxxxxxx> 173.194.77.27:25,*,"SERIALNUMBER=<xxxxxxxxx> 173.194.77.27:25,*,<xxxxxxxx>,Certificate serial number 173.194.77.27:25,*,<xxxxxxxxxx>,Certificate thumbprint 173.194.77.27:25,*,mail.wrightbg.com;www.mail.wrightbg.com;mail.wrightimg.com;autodiscover.wrightbg.com;autodiscover.wrightimg.com;corp-exchange.wrightbg.com,Certificate alternate names 173.194.77.27:25,*,,Received certificate 173.194.77.27:25,*,<xxxxxxxx>,Certificate thumbprint 173.194.77.27:25,>,EHLO CORP-EXCHANGE.wrightbg.com, Then there's nothing more related to gmail logged for 12 minutes, even though I'm sending an email to them every minute. In queue viewer, the connection is shown as active, but no email moves through it. After the 12 minutes, I get this (notice it's a different gmail server) 74.125.140.27:25,*,,attempting to connect 74.125.140.27:25,+,, 74.125.140.27:25,<,220 mx.google.com ESMTP i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,>,EHLO CORP-EXCHANGE.wrightbg.com, 74.125.140.27:25,<,"250-mx.google.com at your service, [66.194.64.143]", 74.125.140.27:25,<,250-SIZE 35882577, 74.125.140.27:25,<,250-8BITMIME, 74.125.140.27:25,<,250-STARTTLS, 74.125.140.27:25,<,250-ENHANCEDSTATUSCODES, 74.125.140.27:25,<,250 PIPELINING, 74.125.140.27:25,>,STARTTLS, 74.125.140.27:25,<,220 2.0.0 Ready to start TLS, 74.125.140.27:25,*,,Sending certificate 74.125.140.27:25,*,"CN=<xxxxxxx> 74.125.140.27:25,*,"SERIALNUMBER=<xxxxxxxxx> 74.125.140.27:25,*,<xxxxxxxx>,Certificate serial number 74.125.140.27:25,*,<xxxxxxxxxx>,Certificate thumbprint 74.125.140.27:25,*,mail.wrightbg.com;www.mail.wrightbg.com;mail.wrightimg.com;autodiscover.wrightbg.com;autodiscover.wrightimg.com;corp-exchange.wrightbg.com,Certificate alternate names 74.125.140.27:25,*,,Received certificate 74.125.140.27:25,*,<xxxxxxxx>,Certificate thumbprint 74.125.140.27:25,>,EHLO CORP-EXCHANGE.wrightbg.com, 74.125.140.27:25,<,"250-mx.google.com at your service, [66.194.64.143]", 74.125.140.27:25,<,250-SIZE 35882577, 74.125.140.27:25,<,250-8BITMIME, 74.125.140.27:25,<,250-ENHANCEDSTATUSCODES, 74.125.140.27:25,<,250 PIPELINING, 74.125.140.27:25,*,3663211,sending message 74.125.140.27:25,>,MAIL FROM:<moni...@wrightbg.com> SIZE=1006, 74.125.140.27:25,>,RCPT TO:<wright...@gmail.com>, 74.125.140.27:25,<,250 2.1.0 OK i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,<,250 2.1.5 OK i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,>,DATA, 74.125.140.27:25,<,354 Go ahead i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,<,250 2.0.0 OK 1363192209 i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,*,3663222,sending message 74.125.140.27:25,>,MAIL FROM:<moni...@wrightbg.com> SIZE=1006, 74.125.140.27:25,>,RCPT TO:<wright...@gmail.com>, 74.125.140.27:25,<,250 2.1.0 OK i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,<,250 2.1.5 OK i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,>,DATA 74.125.140.27:25,<,354 Go ahead i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,<,250 2.0.0 OK 1363192210 i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,*,3663237,sending message It repeats, sending all of the messages in the queue 74.125.140.27:25,>,QUIT, 74.125.140.27:25,<,221 2.0.0 closing connection i23si22850551yhn.39 - gsmtp, 74.125.140.27:25,-,,Local Ideas? Steve Hart Network Administrator 503.491.4343 -Direct | 503.492.8160 - Fax ________________________________ From: Michael B. Smith [mailto:mich...@smithcons.com] Sent: Wednesday, March 13, 2013 9:56 AM To: MS-Exchange Admin Issues Subject: RE: GMail sending woes I've read your last couple of mails on the topic. I'm not getting reports of issues from any of my clients. I would probably create send-connector just for gmail and set the logging on the connector to verbose and then examine some of the SMTP logs. From: Steve Hart [mailto:sh...@wrightbg.com] Sent: Wednesday, March 13, 2013 12:35 PM To: MS-Exchange Admin Issues Subject: OT: GMail sending woes We're on Exchange 2007. Our emails to non-gmail servers are moving normally. I'm having difficulty consistently sending emails to gmail. Emails move normally for an hour or two. Then, the emails build in the queue. The queue is in the "active" state and there are no error messages. After 5 to 15 minutes, all of the email will move. When I telnet to the gmail servers, I get syntax errors (no matter if the emails are currently going through or not) It's possible that gmail is throttling our emails. How can I troubleshoot this? Steve Steve Hart Network Administrator 503.491.4343 -Direct | 503.492.8160 - Fax --- To manage subscriptions click here: http://lyris.sunbelt-software.com/read/my_forums/ or send an email to listmana...@lyris.sunbeltsoftware.com<mailto:listmana...@lyris.sunbeltsoftware.com> with the body: unsubscribe exchangelist --- To manage subscriptions click here: http://lyris.sunbelt-software.com/read/my_forums/ or send an email to listmana...@lyris.sunbeltsoftware.com<mailto:listmana...@lyris.sunbeltsoftware.com> with the body: unsubscribe exchangelist --- To manage subscriptions click here: http://lyris.sunbelt-software.com/read/my_forums/ or send an email to listmana...@lyris.sunbeltsoftware.com with the body: unsubscribe exchangelist
