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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

Alternate Method of Sending Mail

This alternate method of sending email will bypass your mail provider's email server, and therefore bypass the need for STARTTLS and SMTP AUTH support. The mail server we will use will reside on your Macintosh and is called MailShare. It requires System 7 (or 7.0.1, or 7.1, or ...) and can be a little hard to find on the Internet. A local download mirror is here.

Setting up MailShare

Remarkably, all the default settings for MailShare are correct, and there is no set-up required.

Sending Mail

Sending mail using the MailShare method is easy! Once everything is set up properly, just make sure to launch MailShare before attempting to send email. The MailShare Log Window will display your Mac's IP address.

Open your email client's preferences and set the SMTP server address to your own Mac's IP address. For example, if your IP address was 192.168.1.6, your Eudora Lite Configuration window would look like this:

Your email client will connect to MailShare, which will reach out onto the internet and deliver your message. Make sure to quit MailShare when you're done sending mail, to avoid potential security problems.

Unfortunately, since MacTCP doesn't support the loopback address that OpenTransport users get to use, you'll have to retype your Mac's IP address into the SMTP Server field of your email client every time your Mac's IP address changes. For dialup users in particular, this means typing it in every time you dial up.

Troubleshooting

If you run into trouble sending mail with this method, the Debug Window, accessible from the Server menu, can be of assistance. Make sure that your email client is configured correctly to use your IP address for SMTP, and trash your MailShare preferences file.

Another known limitation of this method is that many mail sites use a "black list" to help reduce the amount of spam they receive. If you're using this method and have an internet connection with a dynamic IP address (such as cable, DSL, or dialup), your outgoing mail will be rejected as spam by certain mail providers, notably AOL. These messages will probably have to be sent from a different computer.

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