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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, 2020 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, 2020 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, 2020 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, 2020 at 8:16
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    I have other machines for gaming, just thought it would be cool to be able to work from an old machine. I like the keybaord, I like the looks plus think of a look on people's faces when you pull out a commodore laptop to do some modern work. Priceless ;)
    – Bartek Malysz
    Nov 5, 2020 at 13:50

2 Answers 2

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How about SSH2DOS?

SSH2DOS v0.2.1+SHA256.1 patch by Antti Takala https://github.com/AnttiTakala/SSH2DOS Released on 04-14-2021

The aim was to update the ciphers and protocols to more 2021 standards so the programs would be usable with current ssh servers without the need to change the server configuration to allow less secure connection methods.

https://github.com/AnttiTakala/SSH2DOS/

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    The readme also says: Note that the random number generator used in the program is not cryptographically secure at all. There may also be other security issues so USE AT YOUR OWN RISK. Though depending on the use case this may also not be a serious issue.
    – Vilx-
    Oct 23, 2022 at 12:44
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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, 2021 at 19:39

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