Ole Laursen:
> I got a report that our Postfix server wasn't using TLS on outbound
> connections, and looking in the log, it seems like I get a lot of PIX
> workarounds with both gmail.com and Microsoft's service:
> 
>   postfix/smtp[1243304]: 7BDFA6B7: enabling PIX workarounds: disable_esmtp
> for aspmx.l.google.com[74.125.205.27]:25
> 
> I have not followed Postfix history, but it looks to me that the PIX code
> is more than 20 years old and was introduced to handle old Cisco firewalls.
> Surely that's not the the case for gmail.com and Microsoft? If I try
> telnetting the gmail.com server, I get:
> 
>   telnet aspmx.l.google.com 25
>   Trying 74.125.205.26...
>   Connected to aspmx.l.google.com.
>   Escape character is '^]'.
>   220
> ******************************************************************************

Should have looked like:

    Connected to 74.125.205.26.
    Escape character is '^]'.
    220 mx.google.com ESMTP 
c10-20020a2ea78a000000b0024f3b903d0asi6691935ljf.119 - gsmtp

You are talking to a box-in-the-middle. Good luck doing TLS with that.

        Wietse

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