On Mon, Jan 26, 2015 at 02:05:41AM +0000, srach wrote:

> mail_version = 2.11.3
> 
> Say his mail domain is "clientdomain.com" and his mail server is 
> "client1.clientdomain.com".
> 
> I am working on TLS security of mail from my server to his server.
> 
> I am having handshake problems on the relay, the error is "Cannot start TLS: 
> handshake failure".  Of course if I see logs in great detail for my servers 
> and his domain then I can do the troubleshooting.

Your logs are too verbose.  This just hides the real problem in a torrent
of noise.

> Jan 25 04:27:25 srchmx postfix/smtp[17317]: setting up TLS connection to 
> client1.clientdomain.com[45.3x.xxx.xxx]:25
> Jan 25 04:27:25 srchmx postfix/smtp[17317]: D04EE9086B: Cannot start TLS: 
> handshake failure

You've obfuscated the destination IP address, so no independent
checks of the server's TLS support are possible.

> On the reciever end, that of my client that I do not control server the only 
> log sent to me only says
> 
> ??? Jan 25 04:27:46 client1 postfix/smtpd[20478]: connect from 
> srchmx.myserver.com[171.2xx.xxx.xxx]
> Jan 25 04:27:46 client1 postfix/smtpd[20478]: SSL_accept error from 
> srchmx.myserver.com[171.2xx.xxx.xxx]: lost connection
> Jan 25 04:27:46 client1 postfix/smtpd[20478]: lost connection after 
> STARTTLS from http://srchmx.myserver.com[171.2xx.xxx.xxx]
> Jan 25 04:27:46 client1 postfix/smtpd[20478]: disconnect from 
> srchmx.myserver.com[171.2xx.xxx.xxx]

Resolving TLS handshake problems requires full-package PCAP captures
and wireshark.

> smtp_tls_loglevel = 3

Try loglevel = 1.

> smtp_tls_ciphers = TLS_ECDHE_RSA_WITH_RSA_AES256_GCM_SHA384, high, medium

The above is gibberish:

    http://www.postfix.org/postconf.5.html#smtp_tls_mandatory_ciphers

The documented syntax is *exactly one* of:

    null, export, low, medium, high

The default is almost certainly good enough.  Remove this setting.

> smtp_tls_exclude_ciphers = aNULL, RC4

This too is unnecessary.

> smtp_tls_mandatory_protocols = !TLSv1.1, !TLSv1, !SSLv3, !SSLv2

That's a terrible idea, the remote server probably does not support
TLSv1.2.  Restore the default or disable only:

    smtp_tls_mandatory_protocols = !SSLv2, !SSLv3

> smtp_tls_mandatory_ciphers = TLS_ECDHE_RSA_WITH_RSA_AES256_GCM_SHA384, high

This is wrong.  

    http://www.postfix.org/postconf.5.html#smtp_tls_mandatory_ciphers

> tls_policy
>       clientdomain.com encrypt
> 
> I ask for help to learn how to troubleshoot this better.? Not to have it 
> fixed for me.

Restore sensible default settings.  Your efforts to make things
more fashionably secure are counter-productive.

-- 
        Viktor.

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