Sendmail submission as client

[Alberto Mijares]

Hi guys,

I'm working on FreeBSD 10.2 amd64, Sendmail 8.15.2. This are the
changes I've made so far:

define(`SMART_HOST', `relay.domain.tld')
define(`RELAY_MAILER_ARGS', `TCP $h 587')
FEATURE(`authinfo')
MASQUERADE_AS(`my.domai.tld')
FEATURE(`masquerade_envelope')

the file /etc/mail/authinfo has this line:

AuthInfo:relay.domain.tld  "U:user" "P=base64encodedpassword" "M:PLAIN LOGIN"

and created the hash with

# cd /etc/mail; makemap hash authinfo.db < authinfo; make restart

However, when sending mail, the server relay.domain.tld says:

530 5.5.1 Invalid command: Must issue an AUTH command first

So, Sendmail is not sending credentials, is not honoring authinfo feature.

This is a configuration I've accomplished before, long time ago, so I
wonder if anything has changed from that time (about 3 years).

Any hint on how to debug this issue?

Thanks in advance,


Alberto Mijares