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Is there an SSH client for DOS 6.22 or Windows 3.1 that supports certificates and could be used to connect to AWS or Azure instances, or any other server for that matter? I have another laptop restoration I'm hoping to finish this week, want to find a cool purpose for it rather than just sit there and gather dust.

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    There's sshdos – Brian H Nov 4 '20 at 21:46
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    What are the specs of the laptop? I once set up Linux on a '386 SX with 2 MB of RAM once so it could be used as a dumb SSH terminal, so you may have better luck with an old version of Linux (or FreeBSD) and a new version of SSH. – user722 Nov 4 '20 at 23:17
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    It doesn't need to be supported, it's not like MS-DOS or Windows 3.1 is still supported either. You just need to be able to build a newer SSH for it. – user722 Nov 5 '20 at 4:56
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    A 386SX will take ages to perform the calculations required for a certificate-based connection using current algorithms. You’d probably be better off using it as a plain telnet client to another system which can connect using SSH to the target. – Stephen Kitt Nov 5 '20 at 8:16
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    So in theory I could fit a RPi0W, connect telnet between C386 and RPi and then from RPi hop onto cloud? – Bartek Malysz Nov 5 '20 at 10:26
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If you could use Java on Windows 3.1 there is a SSH client written in pure Java that would work. I use one on a desktop Java system that has been running for 12 years on Windows to avoid having an SSH tunnel. If it works on an old version of Java that still runs on 3.1 is another question.

https://stackoverflow.com/questions/995944/ssh-library-for-java

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    The commenters above worry that modern crypto may be too hard for native code on retro hardware, and you’re proposing to add JVM overhead on top of that? – user3840170 Jan 4 at 19:39

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