Wietse Venema:
> If you look at the non-VPN captures, then you will see the following:
> 
> - In one trace, we see a client ACK 138, followed by a client packet
>   with ".<CR><LF>" (data 443:446, ACK 138, and a timestamp field
>   tht is unlike those of al other packets in the stream).
> 
> - In the other trace, we see that the ACK and ".<CR><LF>" packets
>   are sent as one packet, with a normal timestamp field.
> 
> - After this, the TCP connection is messed up, the server keeps
>   transmitting "Queued as xxx", and the client keeps transmitting
>   QUIT.
> 
> This looks like the VPN mucks with TCP and screws up the protocol.

I verified this another time. On the SMTP client side, there is one packet,
and on the SMTP server side there are two.

Here is a diff -U output for client-side and server-side pcap files.

-TIMESTAMP IP 10.110.2.9.33256 > 10.1.3.134.smtp: Flags [P.], seq 443:446, ack 1
38, win 211, options [nop,nop,TS val 2968348176 ecr 687501956], length 3: SMTP: 
.
+TIMESTAMP IP 10.110.2.9.33256 > 10.1.3.134.smtp: Flags [.], ack 138, win 211, o
ptions [nop,nop,TS val 2968348176 ecr 687501956], length 0
+TIMESTAMP IP 10.110.2.9.33256 > 10.1.3.134.smtp: Flags [P.], seq 443:446, ack 
138, win 211, options [nop,nop,TS val 1 ecr 0], length 3: SMTP: .

On the client side we see that the client sends one TCP packet with
three data bytes (offset 443:446, content ".<CR><LF>"), an ACK for
server offset 138, and Timestamp Value 2968348176 and Timestamp
Echo Reply 687501956.

On the server side we see that the server receives two TCP packets.

- One packet with the same ACK for server offset 138, and the same
Timestamp Value 2968348176 and Timestamp Echo Reply 687501956, as
the client sent, but no data bytes.

- One packet with the same ACK for server offset 138, and the same
three data bytes as the client sent, but with a Timestamp Value of
1 and a Timestamp Echo Reply of 0.

And from here on TCP appears to be stuck. The server repeatedly
sends "Ok: queued as 58CE8C0058<CR><LF>" and the client repeatedly
sends "QUIT<CR><LF>".

Anyway, something is breaking TCP and it isn't Postfix. Maybe the
VPN is trying to be too smart, maybe something in your TCP stack
is trying to shape traffic and messing up.

        Wietse

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