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https://www.freesoft.org/CIE/RFC/1123/109.htm
There are two approaches to timeouts in the sender-SMTP: (a) limit the time for each SMTP command separately, or (b) limit the time for the entire SMTP dialogue for a single mail message. A sender-SMTP SHOULD use option (a), per-command timeouts. Timeouts SHOULD be easily reconfigurable, preferably without recompiling the SMTP code.
https://social.technet.microsoft.com/Forums/en-US/5d1d5a9c-6e05-424c-80d6-e6d0a70dd3df/outbound-smtp-connection-timeout-settingsnot-delivery-timeout-settings
Aug 06, 2010 · I need to change the outbound smtp connection timeout settings on an Exchange 2003 and 2007 server. Here's the issue: I have 2 HT servers and when I take 1 of the HT servers offline, some messages are delayed until they give up on trying the HT that …
https://docs.microsoft.com/en-us/dotnet/api/system.net.mail.smtpclient.timeout
By default, calls to the Send method block until the operation completes. If you set the Timeout property to a positive value, and a Send operation cannot complete in the allotted time, the SmtpClient class throws an SmtpException exception. To send a message and continue executing in the application thread, use the SendAsync method.
https://portal.smartertools.com/community/a87281/default-smtp-in-and-out-command-timeout-settings.aspx
SMTP Out Command Timeout - If the server receives a command that sends large amounts of data and the data stops coming in for this number of seconds, the command will be aborted. By default, the command times out after 60 seconds. In RF 2821 - Section 4.5.3.2 Timeouts 4.5.3.2 Timeouts An SMTP client MUST provide a timeout mechanism.
http://forums.msexchange.org/SMTP_timeout_-_solved!/m_1800409453/tm.htm
Jun 28, 2006 · I could see when the message was trying to be delivered it would show a SMTP connection from my gateway, but it would sit there for a long time and finally disconnect; no message delivered. I tried telnet from my gateway to that mail server.
https://arstechnica.com/civis/viewtopic.php?t=1178200
Jul 17, 2012 · IIs6 SMTP is going to be out of the picture in the next 6 weeks--once the migration from Exchange 2003-2010 is done. There is no AV on the box--lovely, eh... I'll keep digging.
https://answers.microsoft.com/en-us/msoffice/forum/all/office-365-smtp-sending-timeouts/b7f02533-f625-43f2-9508-44cecae4dd61
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https://docs.microsoft.com/en-us/Exchange/mail-flow/queues/message-intervals
The message expiration timeout interval specifies the maximum length of time that an Edge Transport server or Mailbox server (the Transport service) tries to deliver a failed message. If the message can't be successfully delivered before the expiration timeout interval has passed, a non-delivery report (also known as an NDR or bounce message) that contains the original message or the message headers is delivered …
https://support.microsoft.com/en-gb/help/303734/how-to-configure-the-smtp-virtual-server-for-message-delivery
In the Microsoft Management Console (MMC), click to select the SMTP virtual server, and then click Properties on the Action menu. Click the Delivery tab. For First retry interval (minutes), type a value for the time to try delivery before posting the first notification. The default is 15 minutes.
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