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Original poster
Aug 24, 2023
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Hey I’m trying to setup a legacy proxy for older computers to access the internet by installing on a newer device and use the newer Mac as the server. But I’m having issues getting everything up and working. Anyone have a link to an easy to setup guide. A lot of guides out there for Linux and windows but not a lot for Mac. Appreciate any help.
 
The best solution I've found is OldSSL-Proxy - it has a guide attached for how to install it. It should work great with an x86 Mac, and I believe ARM Macs can run x86 images with Docker too, though with probably a significant performance penalty. My own guide, start to finish:
  • Install Docker on the new Mac (the page contains a link to Docker and an install guide for it)
  • run the specified command in a terminal (on the new mac), which will automatically download and initialize the proxy image. If the proxy crashes or shuts down, this same command will also relaunch it.
  • Set up the proxy settings on the old Mac. To do this, just open system settings, click Network, then click the type of connection you use (probably Ethernet or Airport). Then click Advanced, then click the Proxies tab in the bar at the top. Select "Manually" in the drop down, next to "configure proxies". Select the boxes for "Web Proxy (HTTP)" and "Secure Web Proxy (HTTPS)". Then, look to the right, and notice the text field underneath "Web Proxy Sever". You'll need to enter the IP address for the New Mac into it, as well as the port number for the proxy (if you haven't changed the defaults, it's 3128 I believe).

    Note: if your network autoconfigures IP addresses, your computers will sometimes change addresses, and when this happens, it will look like the proxy isn't working at all. You'll probably want to go into your router's settings and reserve an address for your new Mac, so that it always gets assigned the same one. That way, you never have to worry about updating this field on the old Mac.
  • Lastly, you need to open a browser, and enter this address: http://New.Mac.IP.address:3180 (obviously, using your New Mac's IP address instead of the text. As an example, my proxy is http://192.168.1.16:3180)

    Once you do, you should see a page with some files listed in it. You'll probably want the one ending in .crt. Just click it to download, then run keychain access (from your utilities folder), and drag the .crt file into keychain. It should then show up in the certificates tab in the bottom left, with the name "OldSSL Proxy". Finally, all you need to do is right click it, then select "Get Info". Click the triangle next to "Trust", then make sure that all of the fields say "Always Trust". You want OS X to accept this certificate unconditionally, so that everything passes through.
Once you've done this, you're set! All of your HTTPS connections will be seamlessly proxied. It makes certain applications, notably Mail.app, work much better.
 
Thank you!!!! I actually ended up going with wrp which basically loads the pages clickable gifs….works pretty darn well. Who would’ve thought you could use Ie from 1999 to browse modern web haha
 
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Yeah wrp is pretty great too. It's not as seamless as OldSSL and only works for browsing, but it does have the advantage that it lets even very old browsers get on the internet (or at least simulate it). Another similar option is browservice - it requires a slightly newer browser (I think IE 5 was the recommended minimum), but it's a fair bit more convenient.

Glad to hear you got it working!
 
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