To configure Sendmail to send email through Amazon SES using STARTTLS

Question

I follow Amazon SES instruction on the following URL http://docs.aws.amazon.com/ses/lates.../sendmail.html but got no luck.

Since, FreeBSD has no /etc/mail/sendmail.mc, I use the following way to configure sendmail

make

edit the /etc/mail/{host}.mc to add Amazon's lines

make install & make restart

I got 530 Authentication required from Amazon.

By using command line guide on http://docs.aws.amazon.com/ses/lates...mand-line.html I am sure my username and password is correct.

Then, I've googled for FreeBSD sendmail for related answers...I've found there are various ways, including to add TLS, or SASL...etc. But don't know which way will fix the problem.

Is there any easy way and correct way to fix this problem? Thank you very much

@Andrzej A. Filip, Thank you. I decide to give up. Just a note here. I've tried to recompile sendmail with security/cyrus-sasl2-saslauthd by using arved's suggestion, or using a secure tunnel, or re-edit the {host}.mc with different ways, Amazon SES command line test ( It works!!).

Amazon SES documentation is not designed for FreeBSD, it just use Amazon Linux AMI as an example to indicate how to configure sendmail to relay to Amazon SES.

In the beginning, I think it is an easy way to upgrade my old app, however, it takes too much time. For the time spent on this way, I can set up a new EC2 server and forward all the emails to the new server from the old app. So, I decide not to waste time on the path due to poor documentation.

But thank you anyway to help me see the transaction log between my machine and Amazon SES. I would like to highlight this, because maybe someone will need the way to see how they are working.

Answer 1

Sendmail: Sending test messages with SMTP session tracking

Below please find a test script for making sendmail send messages with SMTP session tracking.
WARNING: The script requires root privileges.

#/bin/sh
SENDMAIL_BIN=/usr/sbin/sendmail

# Change sender and recipient as needed in your case
SENDER=john.doe@example.net
RECIPIENT=jane.done@example.com
SUBJECT=test

SENDER_HDR=$SENDER
SENDER_ENV=$SENDER
RECIPIENT_HDR=$RECIPIENT
RECIPIENT_ENV=$RECIPIENT
# -Am    - use sendmail.cf instead of submit.cf
# -i     - do not treat "single dot" line as "END OF MESSAGE"
# -v     - verbose mode (includes SMTP session tracking)
# -d60.5 - track map lookups (including authinfo map lookups)
# -d8.20 - track DNS lookups
$SENDMAIL_BIN -i -v -Am -d60.5 -f$SENDER_ENV -- $RECIPIENT_ENV <<END_OF_MESSAGE
Subject: $SUBJECT
To: $RECIPIENT_HDR
From: $SENDER_HDR

Message Body
END_OF_MESSAGE

Answer 2

also Take a look at the SMTP Authentication Chapter of the Freebsd Handbook http://www.freebsd.org/doc/en_US.ISO8859-1/books/handbook/smtp-auth.html