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SSL, STARTTLS, and SMTP AUTH

Checking today's email with your 68k Macintosh

Introduction and History

Years ago, ARPANet was opened to the public, UUCP was extremely popular, and the Internet was born. A PDP-11/70 was a Killer System and almost all Internet protocols were designed to be easy to implement. Most of them could even be used by a human instead of a client program. Passwords, when they existed at all, were blithely passed over the network as human-readable plaintext, and this practice was acceptable.

Many years have passed since those days existed, and almost every prudent ISP now requires SMTP AUTH on their mail server to help prevent spam. Since POP, IMAP, and SMTP AUTH all require a password exchange for authentication, most sensible mail providers require encryption, to protect the passwords and email you hold dear. What's the problem with all this?

These technologies were developed long before most of the software that we use on our 68ks was written! There are only two 68k email clients that support SMTP AUTH: Green (which seems to have been orphaned) and Mulberry (which is hard to download for 68k). There are NO 68k email clients that support SSL or STARTTLS (SSL for SMTP).

Writing such an email client wouldn't only be difficult. There are many different kinds of 68k Macintoshes, and there are many different kinds of 68k Mac users. No single email program could support all of these. I prefer Eudora Pro 4.2. A Mac Plus couldn't even dream of running such a bloated mail client. Other users may want a file-based instead of database-based client. A better solution would be to devise a way for ANY old email client to work with mail services that require all the latest features. Fortunately, everything we need to do that has already been written, and this document will help you configure it. When configuring Macintosh programs, I'll include screenshots of the popular (and free) Eudora Lite, but the same information applies to any email program you might wish to use.

System Requirements | Top

The Preferred method:

The system requirements for the preferred method of sending mail are:

Open Transport
System 7.1 or higher.
A 68030 or 68040 Processor
16MB of RAM

This method uses your mail provider's SMTP server and communicates with it with SMTP AUTH. The Mac program Baton Mail provides this SMTP AUTH capability.

My own inexhaustive testing seems to have revealed that Baton Mail is not compatible with MacTCP (Classic Networking). Hopefully, a future version of Baton Mail will fix this. Until then, it seems that Baton Mail only works with OpenTransport.

If you've got a powerful enough 68k machine to run OpenTransport (and anything as good as a IIci or better is enough), you'll want to use the Preferred method.

The Alternate method

The Alternate method of sending mail requires only:

System 7.0.1
Hard Drive
4MB of RAM

The following Macs will only work with the Alternate method of sending mail.

Macintosh Plus
Macintosh SE
Macintosh Classic
PowerBook 100
Macintosh II
Macintosh LC

Your email will be sent directly from your 68k Mac, bypassing your mail provider's mail server. With this method comes the risk that your emails will be rejected as "spam", but it's better than not being able to send mail at all.

Other Requirements

In addition to the Macintosh system requirements shown above, you'll need another computer on the same LAN as the Mac to act as a Helper. Any computer running MacOS X, a free UNIX (Linux, NetBSD, OpenBSD...), or Windows 95 or newer will suffice. Another computer running MacOS Classic is unfortunately NOT sufficient. That Beige G3 running MacOS 9 you're using won't work. This helper computer needs to have a static local IP address, so that the Mac can know how to find it.

If you're behind a little "black box" broadband router, your helper probably does NOT have a static local IP address. The easiest way to get one is to look at your TCP/IP settings and crib them all down. Set your Helper to "manual configuration" instead of "DHCP" or "By Server", and fill in all the information you copied down into the boxes where it came from. Now you know your Helper computer's address.

If you don't have a local Helper, there's still hope. See "For the PPP Mac"

sTunnel Configurator

I have written a tiny Macintosh program that will write your sTunnel.conf file for you! It is fairly simple to use: simply download it here, unpack the archive, and double click the Configurator. Once Configurator launches, just answer the questions it asks and you'll generate an sTunel.conf file for your particular needs. You even have the option to copy the configuration information to the clipboard, to paste into your favorite editor, or to save the configuration directly to a file for use without editing.

sTunnel Configurator is Open Source, Free Software distributed under the GNU General Public License. It includes its complete source code, so feel free to make it a better program if that's your thing. It compiles under System 7 using MPW, and includes an appropriate Makefile for MPW Shell. Your mileage may vary if you attempt to compile it under any other environment.

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Text and Images copyright 2005 Tyler Sable. Licensed under the terms of the GNU FDL.
Mirroring of this document is actively encouraged. For details, click here.