ClassicConnect

VCSMaster · Posted: Mon May 26, 2025 10:55 pm Post subject: Email with older clients

Hello! I come today to ask a question: Is there a good way to do email with older clients? I would like to use Eudora on this here iMac G3 running OS 9.2.2 but every email provider I find requires SSL and TLS 1.2/1.3. This leaves me unable to login.

It is my understanding that there is no way to get any TLS past 1.1 on OS 9.2.2, but I have heard of a program called "stunnel" which is supposed to help with this, but I cannot for the life of me figure out where even to begin with this process.

Any recommendations or advice on where to get started with configuring that to work? Thanks.

daniel · **Member** Joined: 09 Sep 2023 Posts: 82 Location: USA

do you have your own domain?
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-Daniel

dkay · Posted: Tue May 27, 2025 12:50 am Post subject:

nick99nack on the WinWorldPC Forum has a guide. You can copy his config and change the smtp and imap server addresses if you aren’t using yahoo
https://forum.winworldpc.com/discussion/12201/e-mail-on-older-systems

Sashi · **Admin** Joined: 03 Sep 2023 Posts: 70

I think Nick should repost such valuable information in Classic Connect.

Cmon Nick, bring your wisdom to us!
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I do stuff with things for reasons.
Fuck it, test in prod.

nick99nack · Posted: Tue May 27, 2025 5:04 am Post subject:

dkay was correct that I did post about it on WinWorld back in 2020, but allow me to post a cleaned up version of that here:

stunnel is the software you'll want to use. You can find downloads for it at https://www.stunnel.org (64-bit only). or if you need 32-bit, you can find installers for those here: https://github.com/josealf/stunnel-win32

stunnel is basically a type of proxy server that connects to the service using SSL/TLS and strips that back to plaintext for your client. Once you install it and edit the config file to match whatever e-mail provider you use, you will then point your mail client at the stunnel proxy server, not the e-mail provider itself. Your client will then retrieve e-mails through the proxy as though it were any other mail server.

To set it up, run the installer, then launch the application. You will see an icon for it in the tray area. By default, stunnel is set up for Gmail. If you want to change that to something else, you will have to edit the configuration file with the right servers and ports, then right-click on the tray icon and reload the configuration. If you are connecting to it from another computer, you may have to configure the firewall to allow access to whatever ports you have stunnel running on.

My configuration file below is set up for AOL. The accept lines allows you to set which computers can connect to stunnel and which ports they may connect on (in this case, 143 for IMAP and 587 for SMTP). To allow any computer on the network to access it, remove all IP addresses and just leave a port number.

My config: