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Re: Mail sent to gmail not making it

From: Elijah Savage (esavagedigitalrage.org)
Date: Tue May 02 2006 - 12:07:16 CDT


> I'm trying to test sending some outgoing mail from my new relay server
> and it looks like most things I send to gmail aren't making it.
>
> I can send a message with the word 'test' in the subject and body and it
> will make it:
>
> May 2 09:21:42 smtp postfix/smtp[1050]: 71ED17FDD:
> to=<jstarkelgmail.com>, relay=127.0.0.1[127.0.0.1], delay=0,
> status=sent (250 2.6.0 Ok, id=31157-02, from MTA([127.0.0.1]:10025): 250
> Ok: queued as BF57C7FE0)
>
> May 2 09:21:42 smtp postfix/qmgr[27352]: 71ED17FDD: removed
>
>
>
> If I send another email with a few paragraphs of text it won't make it
> (notice the last few lines):
>
> May 2 09:22:26 smtp postfix/smtp[1050]: 165D67FDD:
> to=<jstarkelgmail.com>, relay=127.0.0.1[127.0.0.1], delay=0,
> status=sent (250 2.6.0 Ok, id=30922-06, from MTA([127.0.0.1]:10025): 250
> Ok: queued as 556717FE2)
>
> May 2 09:22:26 smtp postfix/qmgr[27352]: 165D67FDD: removed
>
> May 2 09:22:27 smtp postfix/smtp[1059]: 556717FE2:
> to=<jstarkelgmail.com>, relay=gmail-smtp-in.l.google.com[66.249.83.27],
> delay=1, status=sent (250 2.0.0 OK 1146586946 i39si6225476wxd)
>
> May 2 09:22:27 smtp postfix/qmgr[27352]: 556717FE2: removed
>
>
>
> The emails will just sit in the mailqueue for days and never clear out.
> Looking in the logs I am also seeing things like this:
>
> May 2 09:25:10 smtp postfix/smtp[1040]: B400F7FD3: conversation with
> gmail-smtp-in.l.google.com[72.14.205.27] timed out while sending end of
> data -- message may be sent more than once
>
>
>
> Is this just gmail's server being flaky or what?
>
>
>
Jamie,

I have seen this before and it turned out to be a pix firewall issue. Also
a slight search in the postfix archives reveals a lot about this issue.
But I think you actually have a network issue on your side. See Wietse's
comments from the archives. If you do have pix's make sure to try turning
off protocol fixup for smtp.

> Hello,
>
> We've been getting errors of the form "timed out while sending end of
> data" which result in the message getting deferred and resent and the user
> getting multiple copies. It appears postfix is sending a "." but that the
> recieving MTA doesn't register that as an end of data and the connection
> times out.

If this happens with mail larger than some size, then you have
a network configuration problem. Search the FAQ for "path MTU
discovery".

        Wietse