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I recently got internet set up on my new Macintosh Color Classic and with a lot of hardship, set up the WebOne proxy, meaning I can load https websites. Most HTML 3+ websites still don't work in iCab, IE, or Netscape, however.

I wanted to set email up, but neither iCab's client nor Microsoft's Mail and News worked with either of my accounts (GMail, Outlook, and iCloud). I do not have the funds to set up a fancy proxy server, but if there is a free service I am more than open to using it. Is there any easy/free (or very cheap) way to set up email on a System 7 Mac? I'm open to a client or a retro-friendly email service.

Edit: I know of the various proxy options to get email encryption working, but due to my setup I need to hire a VPS in the cloud to host proxies, which is cost-prohibitive. Currently I am piggybacking on a friend's WebOne server, but using his email server may not be secure enough?

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This VOGONS thread covers someone asking a similar question about getting Outlook Express 5 to log into GMail back in 2018.

You have two (possibly three) problems to solve:

  1. The mail host now requiring encryption too new for your vintage machine.
  2. The mail host possibly wanting an authentication method like OAuth that didn't exist back then.

For the latter, GMail's app passwords feature may solve the problem.

For the former, you'll need a proxy like stunnel to terminate the encryption on a modern machine and expose an un-encrypted server to your vintage one.

The potential third problem is that, since services like GMail aren't tested against vintage apps, there could be other compatibility regressions lurking.

If you've got a Raspberry Pi, they suggest legacyweb as a solution that acts as an e-mail proxy, proxies various services like Wikipedia, maps, and weather, and acts as a bridge to allow a legacy wired Ethernet to speak to modern high-encryption WiFi.

Other options they suggest include E-MailRelay, getmail, or, for the more skilled, just running a full-fat e-mail server locally using something like Postfix or Exim and configuring it to allow less secure connections from local clients.

Regarding "Most HTML 3+ websites still don't work in iCab, IE, or Netscape, however.", another option you could use is Web Rendering Proxy, which is sort of like Opera Mini, in that it renders the website on a modern machine and then sends what is effectively an interactive screenshot to the vintage machine.

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  • Postfix is pretty easy to set up with IMAP (Well, it was 20+ years ago when I found a HOWTO.) Modifying it to use gmail wasn’t hard, either. Then, the old Mac can connect to the local Linux server.
    – RonJohn
    Mar 31 at 23:17
  • App passwords are being deprecated this summer, which is why I didn't want to depend on them.
    – gorgo
    Apr 1 at 3:00
  • @gorgo Really? [Insert curse here]. Now I need to find a proxy to run my perfectly modern applications just because Google is so obsessed with shoving OAuth into things that should otherwise have no need to embed a browser engine.
    – ssokolow
    Apr 1 at 3:52
  • I know... :( workspaceupdates.googleblog.com/2023/09/…
    – gorgo
    Apr 1 at 4:53
  • From that blog "If the app you are using does not support OAuth, you will need to switch to an app that offers OAuth or create an app password to access these apps." Apr 1 at 8:16

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