Sean Durkin:
> Meanwhile, I've managed to record a tcpdump of such a failed
> session. What exactly am I looking for there?

- The receiving host's window announcement in the tcp handshake
  and in subsequent ACKs.

- Whether there is a "gap" in the sender packet sequence numbers
  as seen by the receiving host.

Such a gap means that a particular packet is being dropped.

Just to bore you with a few examples of bad middleboxes:

- Shortly after the first Postfix release there was a problem with
  traffic corruption due to a buggy middlebox (a Packeteer traffic
  shaper). The error had a very distinct signature.

- For many years, there were problems with CISCO PIX "firewalls"
  that inspected SMTP traffic but failed to properly handle the
  case that <CR><LF>.<CR><LF> happened to fall on a packet boundary.

- http://www.arschkrebs.de/postfix/postfix_cisco_pix_bugs.shtml
  has other examples where CISCO PIX/ASA "firewalls" will mis-handle
  SMTP traffic in various ways.

In your case, you may have to collaborate with someone who is willing
to send large amounts of random email; hopefully some messages will
trigger the bug, and then the sender and receiver can compare tcpdump
recordings.

        Wietse

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