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Old 02-26-2009, 06:42 AM   #1
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Registered: Feb 2009
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Question Exim4 on Debian not negotiating TLS session...

Fellow citizens of the world,
I am trying to set up exim4 to send mail from a recently built laptop running Debian etch. I type "mail" at the bash prompt and send a test e-mail. I expect to see a new TLS connection to the configured SMTP server (, then a non-trivial amount of data sent on the connection, and finally the test e-mail in the remote mailbox.
What I actually see is the establishment of a new TCP connection to the SMTP server (on port 465), but no TLS negotiation takes place at all. Exim4 just hangs as if it is waiting for the remote server to initiate the TLS handshake or something. Really not sure what's happening at all! Perhaps I am confused...
More precisely, for those who are familiar with the nuts and bolts of TCP/IP, I just see the usual three packet TCP handshake (SYN-SYNACK-ACK), then dead silence. Here's the tcpdump output when I send that test e-mail:

03:49:36.417728 IP (tos 0x0, ttl 64, id 59916, offset 0, flags [DF],
proto: TCP (6), length: 60) >
S, cksum 0xf47d (correct),
4211147563:4211147563(0) win 5840 <mss 1460,sackOK,timestamp 583975
0,nop,wscale 4>
03:49:36.472416 IP (tos 0x0, ttl 243, id 44203, offset 0, flags [none],
proto: TCP (6), length: 64) >
S, cksum 0xa609 (correct),
15231411:15231411(0) ack 4211147564 win 4356 <mss 1452,nop,wscale 0
,nop,nop,timestamp 2993432110 583975,sackOK,eol>
03:49:36.472454 IP (tos 0x0, ttl 64, id 59917, offset 0, flags [DF],
proto: TCP (6), length: 52) >
: ., cksum 0xf554 (correct), 1:1
(0) ack 1 win 365 <nop,nop,timestamp 583989 2993432110>

And that's all she wrote -- no more packets at all.

Here is some version info:
Exim version 4.63 #1 built 20-Jan-2007 10:40:39
Linux HPC 2.6.18-6-686 #1 SMP Fri Dec 12 16:48:28 UTC 2008 i686 GNU/Linux

I used the exim4 config file generated by running 'dpkg-reconfigure exim4-config' with the single line 'tls_on_connect_ports = 465' added near the top. If it will help, I would be happy to send the exim4.conf file, which is 745 lines long.
I hope someone can help me out.
Old 02-27-2009, 03:09 AM   #2
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Registered: Feb 2009
Posts: 2

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A litte more information on this. I looked at, which describes how to configure exim4 to talk TLS to gmail on port 587, not port 465, which I was trying to get to work with an SMTP server at my school. I was able to get gmail:587 to work easily. that to work easily. It turns out also listens on port 465, so I tried to get gmail:465 to work, but it hangs in exactly the same way described above (TCP connection is setup, but TLS negotiation never starts). Thus, it seems there is some problem specifically with port 465. This looks like a bug in exim4 (why would it establish a TCP session and then not send any data?), but I am enough of a newbie to not be certain.

I can use gmail for my purposes, so I will not look into this further.


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