On Mon, Jan 05, 2015 at 03:10:49PM +0100, Matthias Schneider wrote:

> I noticed that many Exchange Servers nowadays have problems with TLS. Is
> there a way to make a fallback to plain if there is a timeout on MAIL FROM?

Postfix 2.12 (almost released, but for now 2.12-20141228 is the
latest snapshot) will by default retry in cleartext when TLS data
transfer fails, in most cases after initially deferring the message.

http://permalink.gmane.org/gmane.mail.postfix.user/243401

http://archives.neohapsis.com/archives/postfix/2013-11/0121.html

https://www.ietf.org/mail-archive/web/tls/current/msg10471.html

You can configure your SMTP client with:

    -o tls_export_cipherlist=aNULL+AES128:aRSA+AES128:RC4-SHA:STRENGTH 

This selects a cipherlist that is something like:

    AECDH-AES128-SHA        SSLv3 Kx=ECDH       Au=None Enc=AES(128)  Mac=SHA1
    ADH-AES128-GCM-SHA256   TLSv1.2 Kx=DH       Au=None Enc=AESGCM(128) Mac=AEAD
    ADH-AES128-SHA256       TLSv1.2 Kx=DH       Au=None Enc=AES(128)  Mac=SHA256
    ADH-AES128-SHA          SSLv3 Kx=DH         Au=None Enc=AES(128)  Mac=SHA1
    ECDHE-RSA-AES128-GCM-SHA256 TLSv1.2 Kx=ECDH Au=RSA  Enc=AESGCM(128) Mac=AEAD
    ECDHE-RSA-AES128-SHA256 TLSv1.2 Kx=ECDH     Au=RSA  Enc=AES(128)  Mac=SHA256
    ECDHE-RSA-AES128-SHA    SSLv3 Kx=ECDH       Au=RSA  Enc=AES(128)  Mac=SHA1
    SRP-RSA-AES-128-CBC-SHA SSLv3 Kx=SRP        Au=RSA  Enc=AES(128)  Mac=SHA1
    DHE-RSA-AES128-GCM-SHA256 TLSv1.2 Kx=DH     Au=RSA  Enc=AESGCM(128) Mac=AEAD
    DHE-RSA-AES128-SHA256   TLSv1.2 Kx=DH       Au=RSA  Enc=AES(128)  Mac=SHA256
    DHE-RSA-AES128-SHA      SSLv3 Kx=DH         Au=RSA  Enc=AES(128)  Mac=SHA1
    AES128-GCM-SHA256       TLSv1.2 Kx=RSA      Au=RSA  Enc=AESGCM(128) Mac=AEAD
    AES128-SHA256           TLSv1.2 Kx=RSA      Au=RSA  Enc=AES(128)  Mac=SHA256
    AES128-SHA              SSLv3 Kx=RSA        Au=RSA  Enc=AES(128)  Mac=SHA1
    RC4-SHA                 SSLv3 Kx=RSA        Au=RSA  Enc=RC4(128)  Mac=SHA1

With RC4-SHA early enough for the 11-year old Microsoft Exchange
servers.

-- 
        Viktor.

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