We have a difficulty delivering to a site running a barracuda appliance.
I can email them from a gmail account, or via a telnet session,
but not via postfix on our SMTP gateway. I've contacted the remote
site from my gmail to discuss it but no progress so far.

I have the default pix conf settings and we are running postfix 2.8.6

In the logs we see it times out.

Mar 21 15:01:30 thabit postfix-internal/smtpd[9296]: 6E7211F44DD:
client=localhost[127.0.0.1]
Mar 21 15:01:30 thabit postfix-internal/cleanup[9274]: 6E7211F44DD:
message-id=<moodlepost153...@acorn.mydomain.ca>
Mar 21 15:01:30 thabit postfix-internal/qmgr[28954]: 6E7211F44DD:
from=<lms.ad...@mydomain.ca>, size=6449, nrcpt=1 (queue active)
Mar 21 15:01:30 thabit postfix-internal/lmtp[9288]: 2A0561F44EE:
to=<usern...@theirdomain.ca>, relay=127.0.0.1[127.0.0.1]:10026,
delay=189085, delays=189084/0.03/0.01/0.3, dsn=2.0.0, status=sent (250
2.0.0 Ok, id=09101-06, from MTA([127.0.0.1]:10027): 250 2.0.0 Ok:
queued as 6E7211F44DD)
Mar 21 15:01:30 thabit postfix-internal/smtp[9198]: 6E7211F44DD:
enabling PIX workarounds: disable_esmtp delay_dotcrlf for
barracuda1.theirdomain.ca[24.224.X.Y]:25
Mar 21 15:11:30 thabit postfix-internal/smtp[9198]: 6E7211F44DD:
conversation with barracuda1.theirdomain.ca[24.224.X.Y] timed out
while sending end of data -- message may be sent more than once

I saw an older article about delivering to a barracuda gateway and
tried the solution with

smtp_discard_ehlo_keyword_address_maps =
hash:/etc/postfix-internal/smtp_discard_ehlo

and that file containing:

24.224.X.Y      pipelining

This setting made no difference in the result and error.

I wonder if the pix settings are not the right fit for this case?

Is there a method to not use the pix workarounds for a single destination?

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