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In order to send my mails from my local Sendmail server to external address, I make it connecting to an authentified SMART HOST provided by my ISP.

The sendmail.cf has the following DS line :

DS[smtp.xxxxxxxxx.org]

and the authinfo file contains :

AuthInfo:smtp.xxxxxxxxxx.org "U:authsmtp" "I:[email protected]" "P:ABCDEFGH" "M:LOGIN PLAIN"

This mechanism works as expected with mails without attachment, or emails with attachement < 4M.

The problem is that when I send a mail with a > 4M attachment, the mail is forwarded to the Smart host, but it is stuck in the client's (typically Outlook) outbox. As a result, the mail keeps getting sent, while it is not removed from the outbox manually.

It seems that the mai server and then the smarthost get the whole mail, but the client abandons the transaction as the timeout has been reached.

I can't find a solution to notice the client that the mail has been successfully received by the server, and does not need to be resent, and I really don't know where to start ...

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  • Do you use any anti-spam or anti-virus milters? [It may introduce delays the clients do not like]
    – AnFi
    Jun 14, 2014 at 4:31
  • Indeed, my sendmail has clamav and spamassassin milters. Is there a way not to execute them dependaing on the message size ?
    – jpicaude
    Jun 14, 2014 at 9:21
  • Try to ask at news:comp.mail.sendmail
    – AnFi
    Jun 27, 2014 at 18:16

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