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Comment by mortenjorck | Hacker News Reader

The biggest surprise for me in reading this was the complete lack of any SSL functionality in the original version of Internet Explorer, rendering most of the modern web not merely broken, but fully inaccessible.

I wonder what the earliest version of Windows would be that can at least establish a connection to a 2020s website out of the box.

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The IE in the screenshots is IE 3.x (I think - judging from the swirlies in the toolbar background), which does have SSL.

The problem is it isn't going to have SSL versions or cipher suites that are compatible with the modern Internet so it's going to be pretty useless.

Out of the box you're looking at probably Vista SP1, or maybe even 7. SNI support is basically mandatory now. You could install older versions of firefox or IE8 for XP, I guess.

Windows 7 RTM cannot install the chocolatey package manager OOTB due to TLS 1.2 expectations, necessitating some work to get Windows up to date with Powershell V3 and such[1]. So maybe Windows 7 SP1, or Windows 8?

[1] https://blog.chocolatey.org/2020/01/remove-support-for-old-t...

About five or six years ago I found an old CD of Windows ME. Having moved on from Windows 95 to NT, 2000 and so forth, I was curious about it. Needless to say, even a few years ago getting on the web with Windows ME out of the box was broken. I eventually found a version of Opera I think which was new enough that I was able to use the Internet. More recently I read of someone using a SOCKS proxy to make using the Internet more functional for an older machine.

Internet Explorer v1 was not really a product. I think the only place I saw it was on a documentation CD which contained HTML files. The original internet pack for Windows 95 came with IE2, which had SSL.

The past couple years SSL has been disappearing completely, and TLS is now required. It didn't exist until at least 1999. So even with SSL support, you'd still be out of luck.

SSL 2 and 3 wouldn't get you anywhere anyway.

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