atom feed5 messages in net.sourceforge.lists.courier-usersRe: [courier-users] [Solved] Unable t...
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John VaskoJul 20, 2012 12:42 am 
Sam VarshavchikJul 20, 2012 4:13 am 
John VaskoJul 20, 2012 2:01 pm 
Sam VarshavchikJul 20, 2012 2:51 pm 
John VaskoJul 21, 2012 4:23 pm 
Subject:Re: [courier-users] [Solved] Unable to Mail Through ATT Uverse ISP
From:John Vasko (
Date:Jul 21, 2012 4:23:13 pm

Sam Varshavchik, thanks for the help!

Sending encrypted mail is now working through ATT Uverse with stunnel with
courier. My esmtpauthinfo file was missing the port as parameter.


Documentation does not show the ,port or /SECURITY= options when looking at: esmtpauthclient This configuration file configures ESMTP authentication for the ESMTP client.
This is a text file of zero or more lines that contain the following fields: relay userid password

The description of esmtproutes is described more explicitly: esmtproutes This file is used by the ESMTP module, and it contains one or more lines in the
following form: domain:relay[,port][/SECURITY=STARTTLS][/SECURITY=NONE]

More info and setup on FreeBSD 9.0:

telnet 587

Trying Connected to Escape character is '^]'. 220 ESMTP ehlo localhost 250-AUTH LOGIN PLAIN XYMCOOKIE 250-PIPELINING 250-SIZE 41697280 250 8BITMIME quit

== Courier Send Mail Through ISP == cd /usr/local/etc/courier/

# ATTUverse Auth Working (Unencrypted?) vi esmtpauthclient,587 PASSWORD vi esmtproutes,587

# ATTUverse Auth Working (Encrypted through stunnel) esmtpauthclient LOCALHOST.EXAMPLE.COM,2525 PASSWORD esmtproutes :LOCALHOST.EXAMPLE.COM,2525

== Stunnel Conf == vi /etc/rc.conf stunnel_enable="YES" cd /usr/local/etc/rc.d/ vi stunnel : ${stunnel_enable="YES"} : ${stunnel_config="/usr/local/etc/stunnel/${name}.conf"} : ${stunnel_pidfile="/var/run/stunnel/${name}.pid"} cd /usr/local/etc/stunnel cp stunnel.conf-sample stunnel.conf vi stunnel.conf chroot = /var/run/stunnel setuid = stunnel setgid = stunnel pid = / options = NO_SSLv2 [attsmtp] client = yes verify = 0 accept = 2525 connect = delay = yes cd /var/run mkdir stunnel chown stunnel:stunnel stunnel service stunnel start telnet localhost 2525 ehlo localhost

== Make Stunnel LISTEN on 2525 on restart (Requires Stunnel 4.53) == Run the default supfile and update all ports (took me like 30 min): csup -g -L 2 -h /usr/share/examples/cvsup/ports-supfile pkgtools was used for upgrading: portsdb -Fu portupgrade stunnel

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:


mail gets bounced with auth required,587/SECURITY=STARTTLS

mail gets bounced with unable to set minimum security,465/SECURITY=SSL3

mail gets stuck in mailq (SSL3 was just a guess and probably an

invalid option),587

mail gets bounced with auth required

UNDELIVERABLE MAIL Your message to the following recipients cannot be delivered: <jo@EXAMPLE.COM>: []:


<<< 530-5.5.1 Authentication Required. Learn more at <<< 530 5.5.1 jv6sm4551948pbc.40

Please advise.

More Info:

The original document that helped me get emails working on my other non-courier machine was: With the exception that I had the following authinfo: |AuthInfo: "U:root" "" "P:xxxxxx" "M:LOGIN PLAIN"| Instead of: |AuthInfo: "" "" "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: <>: []:


<<< 530 authentication required - for help go to

My relevant configuration is below.

Please advise.



That should be,587

/usr/local/etc/courier/esmtpauthclient PASSWORD

And that should be PASSWORD

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