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SSL, STARTTLS, and SMTP AUTH

Checking today's email with your 68k Macintosh

a technical discussion by Tyler Sable, spam at fenestrated separated by dot from net
find me on the 68kMLA forums:: TylerEss

Introduction and History | System Requirements | Receiving Mail with SSL
Sending Mail by the Preferred Method | Sending Mail by the Alternate Method
Future Plans | Using Multiple Accounts | For the PPP (dialup) Mac

Preferred Method of Sending Mail

Setting up the Macintosh

The support for the SMTP AUTH protocol is added to the Macintosh by the program Baton Mail. Its homepage is here, and it can be downloaded from here.

Setting up Baton Mail:

The documentation included with Baton Mail makes it fairly easy to use. Please read the Read Me document included with the distribution. If you're only going to be sending mail from one account, just use the "Default" account that Baton sets up when you first start it. Use the following settings:

SMTP Server: the name or address of your helper computer
SMTP Port: 25
Auth Type: SMTP
Username: your username
Password: your password

Here's what my Baton Mail configuration window looks like this:

Make sure that you fill the username and password correctly: usually, the username is just your username, but for GMail, the "username" is your whole email address. Save your Baton Mail settings and Quit (for now).

Setting up the mail client

Setting up your mail client is easy! Just follow the directions for setting up your mail client. When it asks for the SMTP server address, type

127.0.0.1

For example, my Eudora Lite preferences window looks like this:

This is the special "loopback address" and will make your mail client connect to Baton Mail when sending. Baton Mail will add SMTP AUTH support and connect to sTunnel, which will add SSL support and then connect you to your server.

Client->Baton->sTunnel->Server

Setting up the helper computer

sTunnel Configurator includes everything you need to configure sTunnel simply by answering the questions. Click Here!

Connecting to secure SMTP isn't as simple as connecting to most secure POP servers, but luckily the authors of sTunnel have already thought of that for us. Just add these lines to your stunnel.conf and restart sTunnel:

[servicename]
protocol=SMTP
accept=SMTP
connect=mailserver:serverport

For example, to send mail from my SE/30 via GMail, I have the following lines in my stunnel.conf file:

[gmailSMTP]
protocol=smtp
accept=smtp
connect=smtp.gmail.com:587

Sending Mail

The first step necessary when you're ready to send email is to launch Baton Mail. Then, simply send email as normal. Be sure to Quit Baton Mail when you're done sending mail. This will save RAM and avoid any potential security problems that could come from Baton running all the time.

Troubleshooting

With your mail client setup for 127.0.0.1, launch Baton Mail, and attempt to send some email. Should the sending fail, first turn on the logging option in the Edit menu of Baton Mail. Then turn on the debugging options in sTunnel as in the section on recieving, and try again. The contents of these log files should assist you in discovering the problem, with Baton, with sTunnel, or with your client. Don't forget to turn debug logging off when you're finished!

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Text and Images copyright 2005 Tyler Sable. Distributed under the terms of the GNU FDL.
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