On Wed, Jul 28, 2004 at 12:44:34PM -0700, [EMAIL PROTECTED] wrote:
> 
> I have a mail server behind a obsd 3.5 firewall and I am having timeout errors
> when I try and send an email with a large (5MB or greater) attachment.

  i would have the knee-jerk reaction that this is not due to pf.

> So the actual scenario is a user using Outlook,
<snip>
> after about 3 minutes, the user gets an error saying that the
> connection to the server was terminated.  

  afair, msimn and outlook both have a 3m timeout by default.  i cannot
  say i remember for certain if it has to do with only sending or only
  receiving or both.  it is a slider on the advanced tab of the account
  settings for the servers in question ( on the msimn/outlook ).  it may
  be worth your time to set it to "Long" ( iirc, 5m ) to eliminate that
  variable from the equation ( or at least see if now the timeout is 5m.... )

  if the user is virus-scanning outgoing messages via program on their
  machine, turn that off, and to be safe, utterly exit / endtask the 
  antivirus app.

  if testing the scenario with pf removed from the equation ( eg: a pf.conf
  with as minimal hands-off ruleset as possible: "pass all" and whatever
  natting you _need_ to do ) is not possible in your scenario, test
  a different mailing client on the user's PC.

  i would hope that their mail client would only generate a timeout if  
  and only if they heard nothing back from the other end of the xfer 
  ( the smtp/pop3/imap server ).  so unless you were, in pf, somehow
  blocking a certain reply from the server ( unlikely ), it is probably
  somewhere else to look for the source of problems.

  msimn/outlook have abilities to turn on logging.  this may be of some
  small value to you here too.

  i've got $1 who says it's not pf.

> Here is (what I believe) are the pertinent rules:

  i may suggest that if you are not _CERTAIN_ what the pertinent rules
  are, to post at least the entire pf.conf - if for no other reason
  as so show respect to people whom you are asking to help.  openbsd
  list readers have rightful grounds to be !polite if people do not
  provide to them the thorough scenario.

> Any suggestions on what I might try and/or how to debug would be great! 
> Thanks!

  other than what i say above, get rid of 'flags S/SA'.  if there is
  some proxying antivirus program on the user's PC, who can say for certain
  that between the antivirus and the outlook, one might send and F before
  the other thinks something is done?  windows antivirus programs are,
  each one of them, prone to not working _right now_, *regardless* of 
  "it was working fine yesterday".  

  jared

-- 

[ openbsd 3.5 GENERIC ( jun 7 ) // i386 ]

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