Configuring Postfix relayhost [closed]

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I am trying to configure postfix for using relay host with the following in /etc/postfix/main.cf:

relayhost = [mailtrap.io]:2525
smtp_sasl_auth_enable = yes
smtp_sasl_mechanism_filter = plain
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd

After sending email via telnet localhost 25 postfix log says:

Mar 20 10:49:52 hydra postfix/smtpd[19898]: connect from localhost[127.0.0.1]
Mar 20 10:49:52 hydra postfix/smtpd[19898]: improper command pipelining after MAIL from localhost[127.0.0.1]
Mar 20 10:49:52 hydra postfix/smtpd[19898]: 5F9BC2C30A1: client=localhost[127.0.0.1]
Mar 20 10:49:52 hydra postfix/cleanup[19902]: 5F9BC2C30A1: message-id=<20120320084952.5F9BC2C30A1@hydra>
Mar 20 10:49:52 hydra postfix/qmgr[19890]: 5F9BC2C30A1: from=<a@b.com>, size=290, nrcpt=1 (queue active)
Mar 20 10:49:52 hydra postfix/smtp[19904]: warning: SASL authentication failure: No worthy mechs found
Mar 20 10:49:52 hydra postfix/smtp[19904]: 5F9BC2C30A1: to=<c@d.com>, relay=mailtrap.io[176.9.59.220]:2525, delay=0.32, delays=0.19/0.01/0.13/0, dsn=4.7.0, status=deferred (SASL authentication failed; cannot authenticate to server mailtrap.io[176.9.59.220]: no mechanism available)

SMTP server(relayhost) log:

>>> EHLO hydra
250-Ok Helo 213.160.145.74, Mailtrap SMTP Server
250-AUTH PLAIN
250-NO-SOLICITING
250 SIZE 20000000
>>> QUIT
221 Ok

Any Ideas how to fix?

OS: ubuntu.

Answer 1

The issue is caused by the fact that default postfix SMTP security options doesn't allow to have unencrypted password.

Postfix doc about this issue

The correct configuration in this case will be:

relayhost = [mailtrap.io]:2525
smtp_sasl_auth_enable = yes
smtp_sasl_mechanism_filter = plain
smtp_sasl_security_options = noanonymous
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd

Answer 2

In the config file, you probably need to set smtp_use_tls = yes (refer to configuration in http://mhawthorne.net/posts/postfix-configuring-gmail-as-relay.html)

In addition to the above, I had to make sure the libsasl2-modules were installed:

Run the following commands:

apt-get install libsasl2-modules

/etc/init.d/postfix restart