On Fri, Apr 01, 2016 at 05:20:54PM +0200, Paolo Mioni wrote:
>     I'm writing to ask for help with the following problem. I 
> cannot use outlook365 as a relay host for Postfix.
> I'm using postfix 2.6

(which happens to be 3+ years past its EOL date)

> I receive the following error:
> 
> Apr  1 17:12:19 elrng-backup postfix/smtp[10780]: warning:
> SASL authentication failure: No worthy mechs found

This very warning is mentioned in SASL_README:

http://www.postfix.org/SASL_README.html#client_sasl_enable

Note the "Trouble solving tips" section, first bullet point.

> Apr  1 17:12:19 elrng-backup postfix/smtp[10780]: 428BC2C1699:
> SASL authentication failed; cannot authenticate to server
> smtp.office365.com[132.245.194.242]: no mechanism available

> This is the output of postconf -n on my server:
> 
> alias_database = hash:/etc/aliases
> alias_maps = hash:/etc/aliases
> command_directory = /usr/sbin
> config_directory = /etc/postfix
> daemon_directory = /usr/libexec/postfix
> data_directory = /var/lib/postfix
> debug_peer_level = 2
> html_directory = no
> inet_interfaces = localhost
> inet_protocols = ipv4
> mail_owner = postfix
> mailq_path = /usr/bin/mailq.postfix
> manpage_directory = /usr/share/man
> mydestination = $myhostname, localhost.$mydomain, localhost
> newaliases_path = /usr/bin/newaliases.postfix
> queue_directory = /var/spool/postfix
> readme_directory = /usr/share/doc/postfix-2.6.6/README_FILES
> relayhost = [smtp.office365.com]:587
> sample_directory = /usr/share/doc/postfix-2.6.6/samples
> sendmail_path = /usr/sbin/sendmail.postfix
> setgid_group = postdrop
> smtp_generic_maps = hash:/etc/postfix/generic
> smtp_sasl_auth_enable = yes
> smtp_sasl_password_maps = hash:/etc/postfix/sasl-passwords
> smtp_tls_CAfile = /etc/postfix/ssl/postfix_default.pem

This is likely due to a TLS failure.  Add

smtp_tls_loglevel = 1

to enable logging of TLS activity.

> smtp_tls_security_level = may
> smtpd_sasl_security_options = noanonymous
> unknown_local_recipient_reject_code = 550

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