Check your relay host if support for STARTTLS or not by
using telnet first.

On Thu, 22 May 2014 10:39:57 +0200
[email protected] wrote:

> Hello,
> I have a problem with the configuration of Postfix. I use a Postfix
> as a Smarthost with a external Relayserver. The problem is, that the
> SMTP-Connectioon to the Relay is not crypted with TLS. I use
> "smtp_tls_securtiy_level = fingerprint" to prevent a
> man-in-the-middle attack. The administrator of the relay server says,
> that the POP3 Connection with fetchmail is secured with TLS, TLSv1
> with cipher DHE-RSA-AES256-SHA (256/256 bits) zlib compression. But
> there is no security or crypt with the SMTP. I have no idea, what the
> problem is ... Can you help me? My configuration is the following:
> 
> smtpd_banner = $myhostname ESMTP $mail_name (Debian/GNU)
> biff = no
> 
> append_dot_mydomain = no
> 
> readme_directory = no
> 
> default_database_type = hash
> myhostname = myhost
> alias_maps = hash:/etc/aliases
> alias_database = hash:/etc/aliases
> mydestination = myhost, localhost.localdomain, localhost, 127.0.0.1,
> 192.168.1.22 relayhost = relay.domain.com
> mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128,
> 192.168.1.0/24 mailbox_size_limit = 0
> recipient_delimiter = +
> inet_interfaces = all
> inet_protocols = all
> 
> smtpd_tls_cert_file = /etc/ssl/private/server.crt
> smtpd_tls_key_file = /etc/ssl/private/server.key
> smtpd_tls_CAfile = /etc/ssl/certs/ca-certificates.crt
> smtpd_tls_security_level = may
> smtp_tls_mandatory_ciphers = high
> smtpd_tls_mandatory_protocols = !SSLv2, !SSLv3
> smtpd_tls_session_cache_database = hash:${data_directory}/smtpd_scache
> 
> smtp_tls_security_level = fingerprint
> smtp_tls_mandatory_ciphers = high
> smtp_tls_mandatory_protocols = !SSLv2, !SSLv3
> smtp_tls_fingerprint_digest = md5
> smtp_tls_policy_maps = hash:/etc/postfix/tls_policy
> smtpd_tls_session_cache_database = hash:${data_directory}/smtpd_scache
> smtpd_tls_received_header = yes
> smtpd_tls_loglevel = 1
> smtp_tls_loglevel = 1
> 
> smtp_sasl_auth_enable = yes
> smtp_sasl_security_options = noanonymous
> smtp_sasl_password_maps = hash:/etc/postfix/sasl_password
> smtp_sender_dependent_authentication = yes
> 
> sender_canonical_maps = hash:/etc/postfix/sender_canonical
> sender_dependent_relayhost_maps = hash:/etc/postfix/sender_dependent
> 
> mailbox_command = /usr/lib/dovecot/deliver
> message_size_limit = 104857600
> 
> smtpd_sasl_type = dovecot
> smtpd_sasl_path = private/auth
> smtpd_sasl_auth_enable = yes
> smtpd_recipient_restrictions =
>         permit_sasl_authenticated,
>         reject_unauth_destination,
>         permit_tls_clientcerts

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