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macos – Connecting legacy Mac OS (10.3.9) to fashionable HTTPS through TLS – Ask Completely different


As you famous, the issue is that your OS X doesn’t help fashionable variations of the SSL protocol, reminiscent of TLS 1.2. Wikipedia, like many fashionable web sites, doesn’t help older variations of SSL. This creates an deadlock the place neither can speak to one another. Updating root certificates will not assist, as a result of your Mac and the server don’t converse the identical language.

As a substitute, you want a translator—a bit of software program which sits between you and the server, intercepts your site visitors, and modifies it to be suitable. That is known as a “man-in-the-middle” or “MiTM” proxy server. The proxy will decrypt and re-encrypt your site visitors earlier than sending it on its manner.

For Macs working not less than OS X 10.6, I created a turn-key resolution to arrange a neighborhood MiTM proxy server: https://jonathanalland.com/old-osx-projects.html. Nevertheless, this may not work on OS X 10.3. Sadly, I do not know of any MiTM proxy software program that may run in your OS.

So, what you need to do as an alternative is ready up an MiTM proxy server on a second machine, reminiscent of a Raspberry Pi or a contemporary PC, after which connect with that proxy out of your previous Mac.

As a result of this entails networking a number of machines, precise directions will rely in your setup, however it might work! Though the proxy server on the web page linked above requires OS X 10.6, you should still need to reference the Squid configuration file included within the package deal as a place to begin.


P.S. And even when your OS supported fashionable protocols, there could be the difficulty of cipher suites! My OS, OS X 10.9 Mavericks, helps TLS 1.2. Nevertheless, I can’t connect with Wikipedia with out my proxy server, as a result of Mavericks lacks help for contemporary cipher suites, and Wikipedia doesn’t help older cipher suites.

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