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All e-mail sent from a yahoo.com server to my domain fails to be correctly received. The difference between yahoo.com and other domains is that they open with HELO rather than EHLO and therefore attempt to send the data in one part rather than in chunks (as I understand it).

Looking at the wikipedia example communication it seems that we are conforming to the protocol our side. When we expect data to arrive with us however the yahoo server fails to reply leading to a timeout.

2010-10-27T09:17:15.52...-,,Local
2010-10-27T09:17:18.11...+,,
2010-10-27T09:17:18.11...*,SMTPSubmit SMTPAcceptAnySender SMTPAcceptAuthoritativeDomainSender AcceptRoutingHeaders,Set Session Permissions
2010-10-27T09:17:18.11...>,"220 remote.ourserver.co.uk Microsoft ESMTP MAIL Service ready at Wed, 27 Oct 2010 10:17:17 +0100",
2010-10-27T09:17:18.13...<,HELO omp1009.mail.ukl.yahoo.com,
2010-10-27T09:17:18.13...>,250 remote.ourserver.co.uk Hello [xxx.xxx.xxx.xxx],
2010-10-27T09:17:18.14...<,MAIL FROM:<[email protected]>,
2010-10-27T09:17:18.14...*,08CD4019188CB09A;2010-10-27T09:17:18.111Z;1,receiving message
2010-10-27T09:17:18.14...>,250 2.1.0 Sender OK,
2010-10-27T09:17:18.16...<,RCPT TO:<[email protected]>,
2010-10-27T09:17:18.16...>,250 2.1.5 Recipient OK,
2010-10-27T09:17:18.17...,<,DATA,
2010-10-27T09:17:18.17...,>,354 Start mail input; end with <CRLF>.<CRLF>,
2010-10-27T09:19:08.19...

I am stumped as to what to try, I attempted to manually telnet and send an e-mail but I get rejected as I don't have a valid server to send from (I get refused as potential junk).

I have access to the logs of the box but not easy access to the config. Any advice would be greatly appreciated.

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    Can you do capture the network traffic on your email server? If so, send an email from yahoo and another one from a different domain. Then, you can compare the two dumps. This may give you a hint.
    – Khaled
    Oct 31, 2010 at 11:27
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    What kind of firewall are you using? Some have protocol awareness and restrict the commands/traffic format that they will allow through (PIX "fixup" for example).
    – flooble
    Oct 31, 2010 at 12:20
  • I'm pretty sure in the SMTP connector there is an option to take both EHLO and HELO, Oct 31, 2010 at 14:24

1 Answer 1

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It shouldn't have anything to do with the remote server sending HELO instead of EHLO, as Exchange server supports both. You can see in your log file entry that eveything is going smoothly until your Exchange server issues a 354 response, which means "give me the message", and then it dies. Is there more in the log after the last line that you've posted?

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  • Unfortunately not, the next log message is from 19:08 and precedes a new successful message.
    – gav
    Nov 1, 2010 at 11:33
  • In that case then Khaled's suggestion would be the thing to do.
    – joeqwerty
    Nov 1, 2010 at 12:24

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