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a) Does this occur on emails to varying destinations, or only to particular ones?<br />
b) Are you relaying outgoing email out through a gmail MTA?<br />
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If it was the latter, then the symptoms suggest graylisting of your MTA by google. &nbsp;In that case you might try a different outgoing relay such as SMTP2Go.
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a) Does this occur on emails to varying destinations, or only to particular ones?
b) Are you relaying outgoing email out through a gmail MTA?

If it was the latter, then the symptoms suggest graylisting of your MTA by google.  In that case you might try a different outgoing relay such as SMTP2Go.

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They have not given me any more &nbsp;examples but I am assuming different ones. I do not think we were graylisted as that would have stopped the whole email flow and we would have noticed it.
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They have not given me any more  examples but I am assuming different ones. I do not think we were graylisted as that would have stopped the whole email flow and we would have noticed it.

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<a href="https://filedb.experts-exchange.com/incoming/2018/05_w19/1311434/smtp.JPG" target="_blank" title="Message Header (24 KB)"><img alt="Message Header" class="file-block lazyload" style="max-width: 800px;" data-src="https://filedb.experts-exchange.com/incoming/2018/05_w19/800_1311434/smtp.JPG" /></a>Hello,<br />
<br />
We are having some random smtp problems. I am trying to troubleshoot this one in particular. The message header shows it took 136 days for the message to actually get processed by the smtp server. I am not sure what logs/info to look for to find more information. It took 136 days to send from our smtp to Gmail relay. Can you please help?
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smtp.JPG

Hello,

We are having some random smtp problems. I am trying to troubleshoot this one in particular. The message header shows it took 136 days for the message to actually get processed by the smtp server. I am not sure what logs/info to look for to find more information. It took 136 days to send from our smtp to Gmail relay. Can you please help?

Random SMTP Relay Issues

Within Internet message handling services (MHS), a message transfer agent or mail transfer agent (MTA) or mail relay is software that transfers electronic mail messages from one computer to another using a client–server application architecture. A MTA implements both the client (sending) and server (receiving) portions of the Simple Mail Transfer Protocol (SMTP). The terms mail server, mail exchanger, and MX host may also refer to a computer performing the MTA function. The Domain Name System (DNS) associates a mail server to a domain with mail exchanger (MX) resource records containing the domain name of a host providing MTA services.

Email Servers

SMTP

Google’s Gmail is a free email service that allows users to access their email on the web or by using third-party programs that synchronize email content through POP or IMAP protocols.

Gmail

IIS is Internet Information Services, the web server included with Windows Server operating systems. All current versions are built on a modular architecture; modules can be added or removed individually so that those required for specific functionality are installed. The full installation of IIS includes HTTP, security, content, compression, caching, logging and diagnostics.