Dear all,

This one has got me totally stumped, and I'm hoping that someone on the list has
seen something like this before or has some ideas on how to troubleshoot it more
than I have.

This is courier 0.59 on Ubuntu Hardy (running in a virtual machine -
linux-vserver) from the hardy-backports repository.  I have a user who cannot
send secure SMTP through our server.  He's tried Tbird 3 on XP and Vista and
neither can send reliably.  It times out 3 out of 4 times.  The 4th time, it
sits for a long time, but eventually goes through.

POP3S and IMAPS both work fine.  Sending through SMTP (no encryption) works
fine.  Neither SSL over port 465 nor STARTTLS over port 25 work - they both
exhibit the same 3/4 times it hangs and times out.

Tbird on his machine can send just fine through a Communigate Pro server running
on a virtual machine on the same host.

He has cygwin installed on the XP machine so on his end we tried

openssl s_client -connect our_server:smtps -crlf
and
openssl s_client -connect our_server:smtp -crlf -starttls smtp

and both commands show the same behavior - they hang 3 out of 4 times - they
show "Connected", but never get any farther - no certificate, nothing.  We tried
changing the -cipher switch and using different ciphers, but they all act the
same way.

If I watch the connection on the server side using tcpdump, I see the 2 machines
handshake, and then they sit there.  Our server sends an ACK repeatedly but
nothing every comes back.  But from his side, it appears the same way.  (He
doesn't have a sniffer on his machine, so I can't actually watch it.)  The
machines connect, and then just sit there.

Any ideas what else I can try?  Would "-debug" on openssl on cygwin show me
anything other than the connection sitting there?  There's hundreds of accounts
on this machine, and no one has any problems but him.  But he's very tech savvy,
and so when he says he's tried X, Y, and Z and it doesn't work, I believe him.
He's not someone who will try connecting to "gmail.cmo" and then complain
bitterly that it doesn't work. :-)

I'm open to whatever thoughts you may have.  I have no idea where to go next to
troubleshoot this.

TIA

Jeff Jansen

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