It seems like the continued evolution of TLS is a huge barrier to retrocomputing with current networks. Relatedly, I happened to be writing some TLS code on a bit of a side project and I was curious on what old OSs I could get it on with minimal effort. I found the builtin SChannel on Windows XP for example cannot interact with www.google.com at all, or even some of my own TLS-enabled hosts that I maintain myself.
For projects with source available or that you're hacking on, it's not very hard to build libressl. It's a shame that some of these older OSs probably can't have support bolted on for 1st party APIs. Of course, they also are probably full of security holes and you probably don't want them on the public internet anyway.
Another barrier some day will be that those old systems are ipv4-only.
> It's a shame that some of these older OSs probably can't have support bolted on for 1st party APIs.
What first-party APIs? As far as I'm aware, classic Mac OS never had native SSL/TLS support -- every application which needed it (mostly web browsers in that era) included their own implementation.
For projects with source available or that you're hacking on, it's not very hard to build libressl. It's a shame that some of these older OSs probably can't have support bolted on for 1st party APIs. Of course, they also are probably full of security holes and you probably don't want them on the public internet anyway.
Another barrier some day will be that those old systems are ipv4-only.