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Microsoft IIS SMTP Virtual Server Errors

Posted on 2013-11-22
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Last Modified: 2014-04-13
Hi Experts,

I have a Windows Server 2008 R2 running the SMTP service/Virtual SMTP server.  I point many different applications to this to send alerts/notifications, etc and it has grown to become a critical service.  I haven't configured the service to use another relay at this point.

Recently, mail has really been delayed.  I enabled logging through the IIS 6 manager and I'm seeing messages like this.  I've checked with the email provider at the other end and there are no issues.  I have mostly defaults in the Virtual SMTP settings.  Any thoughts?  Since we rely on this service so much is it worth looking into another solution at this point?  I've also tried sending messages to other domains with similar results.

OutboundConnectionResponse SMTPSVC1 SERVER-VS4 - 25 - - 220+******************************************************** 0 0 60 0 296 SMTP - - - -
OutboundConnectionCommand SMTPSVC1 SERVER-VS4 - 25 EHLO - SERVER-VS4.SERVERmedical.local 0 0 4 0 312 SMTP - - - -
OutboundConnectionResponse SMTPSVC1 SERVER-VS4 - 25 - - 250-inbound94.exchangedefender.com+Hello+static-XX-YY-154-82xxx.xxx.xxxx.net+[XX.YY.154.82],+pleased+to+meet+you 0 0 122 0 390 SMTP - - - -
OutboundConnectionCommand SMTPSVC1 SERVER-VS4 - 25 MAIL - FROM:<noreply@SERVERmedical.com> 0 0 4 0 390 SMTP - - - -
OutboundConnectionResponse SMTPSVC1 SERVER-VS4 - 25 - - 250+2.1.0+<noreply@SERVERmedical.com>...+Sender+ok 0 0 51 0 686 SMTP - - - -
OutboundConnectionCommand SMTPSVC1 SERVER-VS4 - 25 RCPT - TO:<sgendron@SERVERmedical.com> 0 0 4 0 686 SMTP - - - -
OutboundConnectionResponse SMTPSVC1 SERVER-VS4 - 25 - - 250+2.1.5+<sgendron@SERVERmedical.com>...+Recipient+ok 0 0 55 0 811 SMTP - - - -
OutboundConnectionCommand SMTPSVC1 SERVER-VS4 - 25 DATA - - 0 0 4 0 811 SMTP - - - -
OutboundConnectionResponse SMTPSVC1 SERVER-VS4 - 25 - - 354+Start+mail+input;+end+with+<CRLF>.<CRLF> 0 0 44 0 811 SMTP - - - -
OutboundConnectionResponse SMTPSVC1 SERVER-VS4 - 25 - - 451+Please+try+again+later 0 0 26 0 1123 SMTP - - - -

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Question by:polaris101
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by:florin_s
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Simon Butler (Sembee) earned 2000 total points
ID: 39671542
Looks like there is a Cisco device involved. Do you have a Cisco PIX/ASA ?
If so, disable the SMTP scanning facility on it, as that can cause email delivery problems.

Simon.
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