My new project is getting Sendmail to work like I want it to. I'm a big fan of taking the path of least resistance, and so far doing a full Slackware install has provided me with everything I want with only little tweaks to configuration files and such. I'm hoping it will be relatively easy to get Sendmail doing what I want.

I'm running Slackware 9.1, upgraded to -current via SWareT, with the 2.6.5 kernel. Everything is pretty stock. I am using dyndns.org to make sure username.dyndns.org always points to my computer. There's no problem with that, as all of the dyndns.org updating is handled automatically by my router.

I am using Sendmail v8.12.11. Sendmail is started up automatically via /etc/rc.d/rc.sendmail. In /etc/inetd.conf I uncommented the line

pop3 stream tcp nowait root /usr/sbin/tcpd /usr/sbin/popa3d

I used netconfig to change my hostname to username and my domain name to dyndns.org. I ran the command

cp /usr/share/sendmail/sendmail-slackware-tls.cf /etc/mail/sendmail.cf

(I am hoping this allows me to use encrypted authentication.) I installled cyrus_sasl-2.1.18-i486-1jgr.tgz from http://www.linuxpackages.net . Made a symbolic link from /usr/local/lib/sasl2 to /usr/lib/sasl2 . I rebooted.

So I start testing things out. I use pine to check things out.
Mail from user@username.dyndns.org to root@username.dyndns.org ----> OK
Mail from root@username.dyndns.org to user@username.dyndns.org ----> OK
Mail from user@username.dyndns.org to username@hotmail.com --------> OK
Mail from username@hotmail.com to user@username.dyndns.org --------> OK

So far, so good, huh?

The problems begin.

Next, I go to work and try to set up Outlook Express to use my handy-dandy new mail server. I set the SMTP server to username.dyndns.org and the POP3 server also to username.dyndns.org . I click on (sic) "Server requires Authenication" and, feelibng lucky, I click on the (sic) "Server Requires SSL". Doesn't work. I get rid of the (sic) "Server Requires SSL" and try again. Looks like we are in cooking now. So I decide to test it out.

Recieve Messages from user@username.dyndns.org's mailbox -----> OK
Mail from user@username.dyndns.org to root@username.dyndns.org ----> OK
Mail from user@username.dyndns.org to username@hotmail.com --------> FAIL

I get the error message "Relaying Denied". DOH!!! So now, here's my questions. Why doesn't the SSL work? What am I missing? I am sure it is simple, but I'm new to the whole sendmail thing. Also, how do I make it so that I can use my mail server to send messages to remote hosts. I don't want to simply add my works host to a list of those allowed, as I would like for anyone I give an account to to be able to use my SMTP server from wherever they are at. The prefered solution seems to be something called SMTP AUTH, but it doesn't seem to be compiled into the Slackware version of Sendmail. I would really prefer not having to recompile Sendmail if at all possible.

Now some more of my problem. I installed the cyrus_sasl-2.1.18-i486-1jgr.tgz package, and part of my question was, why doesn't SSL seem to be working. I checked my /etc/var/maillog file and found the following:

Apr 30 13:32:53 username sm-mta[1441]: STARTTLS=server: file /etc/mail/certs/smtp.cert.pem unsafe: No such file or directory

Of coarse it doesn't work, I don't have any certificates! DUH on my part. So how so I make certificates so that there IS a file /etc/mail/certs/smtp.cert.pem ?

So I'm still looking for answers. Here's what I did next.

mkdir /var/state/saslauthd
/usr/bin/saslauthd -a shadow

Don't really know if that is something I was supposed to do or not. It made three files in /var/state/saslauthd , namely mux, mux.accept, and saslauthd.pid . I notice that when I reboot, those three files are gone. Am I getting somewhere? Didn't seem to change anything for me.

Still trying to get on the right track, I try the following:

/etc/ssl/misc/CA.sh -newcert

That makes me a file called /etc/ssl/misc/newreq.pem . Wow, I can feel I'm getting warmer. Now I actually have a file that ends with .pem. No idea what to do with it, though.

Any help would be greatly appreciated. I have tried to give all of the important details, but I would be happy to supply any more necessary to figure out how to get this thing working.

Thank a whole bunch for any help,

Shilo