The misplaced colon was a typo in my email. The configuration files are as they should be on the server, and outgoing email still isn't working. I hope that didn't ruin my chances in getting help with my issue.

I tried some variations of esmtproutes (and corresponding changes in esmtpauthclient when trying with gmail) but I get the same "authentication required" error. See Below:

esmtproutes
 :smtp.att.yahoo.com,587
 >> mail gets bounced with auth required

 :smtp.att.yahoo.com,587/SECURITY=STARTTLS
 >> mail gets bounced with unable to set minimum security

 :smtp.att.yahoo.com,465/SECURITY=SSL3
>> mail gets stuck in mailq (SSL3 was just a guess and probably an invalid option)

 :smtp.gmail.com,587
 >> mail gets bounced with auth required

UNDELIVERABLE MAIL
Your message to the following recipients cannot be delivered:
<[email protected]>:
    gmail-smtp-msa.l.google.com [173.194.79.109]:
>>> MAIL FROM:<[email protected]> BODY=7BIT SIZE=795
<<< 530-5.5.1 Authentication Required. Learn more at
<<< 530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 jv6sm4551948pbc.40

Please advise.

More Info:

The original document that helped me get emails working on my other non-courier machine was:
http://qiaoyang.blogspot.com/2007/08/sendmail-auth-ssl-tunnel-att-yahoo.html
With the exception that I had the following authinfo:
|AuthInfo: "U:root" "I:[email protected]" "P:xxxxxx" "M:LOGIN PLAIN"|
Instead of:
|AuthInfo: "U:[email protected]" "I:[email protected]" "P:xxxxxx" "M:LOGIN PLAIN"|

On 07/20/2012 04:13 AM, Sam Varshavchik wrote:
John Vasko writes:

On FreeBSD 9.0 trying to send mail from courier's cone I get bounced messages with:
UNDELIVERABLE MAIL
Your message to the following recipients cannot be delivered:
<[email protected]>:
     smtp1.sbc.mail.am0.yahoodns.net [67.195.15.66]:
>>> MAIL FROM:<[email protected]> BODY=7BIT SIZE=795
<<< 530 authentication required - for help go to http://help.yahoo.com/sbc/dsl/mail/pop/pop-11.html

My relevant configuration is below.

Please advise.

-------------

/usr/local/etc/courier/esmtproutes
  smtp.att.yahoo.com,587

That should be

:smtp.att.yahoo.com,587

/usr/local/etc/courier/esmtpauthclient
  :smtp.att.yahoo.com [email protected] PASSWORD

And that should be

smtp.att.yahoo.com [email protected] PASSWORD

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