Several years ago, I had trouble delivering to an old exchange server
while trying to enforce TLS. I'm not sure if this applies to your
situation, but this worked for me. 

In main.cf, I have 

smtp_tls_policy_maps = hash:/etc/postfix/tls_policy 

In tls_policy, I added 

domainname  encrypt ciphers=low
exclude=MD5:SRP:PSK:aDSS:kECDH:kDH:SEED:IDEA:RC2 

On 2020-11-30 1:07 pm, SysAdmin EM wrote:

> I use Postfix as an SMTP server, in the last few days I have started to see 
> an error delivering mail to some servers.
> 
> I am trying to deliver an email to a Server with Microsoft Exchange 2007 and 
> I receive the following message.
> 
>> Nov 30 15:29:40 smarthost04-ded postfix-out/qmgr[9305]: 56253920A60:
>> from=<fvid...@infoauto.com.ar>, size=7238, nrcpt=1 (queue active) Nov
>> 30 15:29:40 smarthost04-ded postfix/smtp[9335]: 32FEC920C41:
>> to=<fvid...@exchange.infoauto.com.ar>,
>> relay=127.0.0.1[127.0.0.1]:10026, delay=0.24, delays=0.1/0/0.04/0.09,
>> dsn=2.0.0, status=sent (250 2.0.0 Ok: queued as 56253920A60) Nov 30
>> 15:29:40 smarthost04-ded postfix-out/smtp[9312]: 56253920A60: Cannot
>> start TLS: handshake failure Nov 30 15:29:40 smarthost04-ded
>> postfix-out/smtp[9312]: 56253920A60:
>> to=<fvid...@exchange.infoauto.com.ar>,
>> relay=exet02.hostmar.com [1][200.58.120.69]:25, delay=0.12,
>> delays=0.09/0/0.03/0, dsn=4.7.5, status=deferred (Cannot start TLS:
>> handshake failure)
> 
> I have read the documentation but I cannot understand why this error occurs.
> 
> This is my configuration
> 
> ```
> postconf mail_version
> mail_version = 3.5.2
> 
> smtp_tls_exclude_ciphers = MD5,SRP,PSK,aDSS,kECDH,kDH,SEED,IDEA,RC2,RC5,RC4
> smtp_tls_protocols = !SSLv2:!SSLv3
> smtpd_tls_cert_file = /etc/pki/tls/certs/linux.ferozo.com.pem
> smtpd_tls_key_file = /etc/pki/tls/private/linux.ferozo.com.key
> smtpd_tls_security_level = may
> smtpd_tls_session_cache_database = btree:/var/lib/postfix/ssl/smtpd_ssl_cache
> smtp_tls_security_level = may
> smtp_tls_session_cache_database = btree:/var/lib/postfix/ssl/smtp_ssl_cache
> 
> ```
> 
> Here I make a connection to the destination server
> 
> ```
> posttls-finger -c -Ldebug "exet02.hostmar.com [1]"
> posttls-finger: initializing the client-side TLS engine
> posttls-finger: setting up TLS connection to exet02.hostmar.com 
> [1][200.58.120.69]:25
> posttls-finger: exet02.hostmar.com [1][200.58.120.69]:25: TLS cipher list 
> "aNULL:-aNULL:HIGH:MEDIUM:+RC4:@STRENGTH:!aNULL"
> posttls-finger: SSL_connect:before/connect initialization
> posttls-finger: SSL_connect:SSLv2/v3 write client hello A
> posttls-finger: SSL_connect error to exet02.hostmar.com 
> [1][200.58.120.69]:25: lost connection
> ```
> Any ideas??
> 
> Regards,
 

Links:
------
[1] http://exet02.hostmar.com

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