Gregory's ServerTurns out if I use something like Git Bash that uses OpenSSH instead of Putty/WinSCP's different implementation, I can connect just fine! I am currently looking into alternatives and learning about the state of ssh in windows in 2021 because frankly I haven't changed my workflow since ~2001
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 @objelisks oh I mean I used putty for years specifically to not deal with linuxy stuff on windows. my solution was always: log in to a linux machine and do my work there.  @darius Putty does seem to be “retired to a farm upstate”. It was a great tool for a long time, but hasn’t kept up to date, is no longer supported by its original author and newer alternatives are often recommended. Windows 10 has the (real) OpenSSH client built-in and out of the box these days (and an OpenSSH server as an easy to install optional feature). I don’t know of GUI tools like WinSCP to take advantage of it though. @darius I'd not used Windows for about as long as you've been using PuTTY. Using Windows 10, and discovering the Linux subsystem where I can do stuff through bash is a game-changer! If I needed to, I could go back to it as my main OS, now that this is possible.  @darius oh strange issue :/ I've been considering just using Win's SSH & OpenSSH very recently (because it's apparently less of an issue if you use ssh private keys + some apps like Github Desktop)... I tested using ConEmu's tasks to start preconfigured SSH sessions... but then I had some weird display bugs in nano after resizing a window, and decided to stick to Putty(/Kitty) for now. Mh.  @darius I know you've found your workflow solution already (and you have been incredibly patient communicating that to everyone!) so I'm not offering advice, but: is there any chance you'd be willing and able to share the version and configuration of the sshd on the listening side? I would really love to try to dig into the exact underlying issue(s) here, even if just for my own edification! @gnomon `sshd -v` gives me "OpenSSH_7.6p1 Ubuntu-4ubuntu0.3, OpenSSL 1.0.2n 7 Dec 2017". I don't know if that's what you are looking for re: version, but it's the same as a different server that was accepting connections just fine. The /etc/ssh/sshd_config on both servers, working and not, is identical too. Is there another file I should be looking at? @darius there could be: sshd's config language is, uh... I'm going to go with "surprisingly versatile" (values can be defined as the results of external commands run at value-read time? Conditionals? Pattern matching??) so the config file itself could be identical but its complete specification could depend on other files.  @darius windows actually has a built-in ssh client these days. I use it with windows terminal and it works pretty well. https://docs.microsoft.com/en-us/windows/terminal/tutorials/ssh |
@darius i use git bash for my windows linuxy stuff, i dunno how to get it to work otherwise