Windows 10: Windows not accepting key for SSH key-based authentication?

I'm trying to use key-based authentication to SSH into my Windows machine (running Windows 10 Pro, Insider build 21337.1000) from a MacBook Air running macOS 10.15.7 Catalina. Password-based auth works fine but whenever I try key-based auth it just...doesn't work. It falls back to my password every time. I've added my Mac's public key to ~/.ssh/authorized_keys and even tried adding it to C:\ProgramData\ssh\administrators_authorized_keys because my Windows user account has administrator permissions...but that didn't work. I also tried commenting these two lines out in my sshd_config file:

Match Group administrators AuthorizedKeysFile __PROGRAMDATA__/ssh/administrators_authorized_keys

...but that didn't work either. If I use the same file to restrict the PC to key-based auth and then try to SSH in from the Mac (with its key added to both authorized_keys files) I get an access denied error (because I didn't provide a matching key and password auth is disabled).

I'm not sure what else to try. I restarted the sshd service between each of those changes to ensure they took effect properly...yet nothing worked. I also tried using the Termius app on my iPhone (SSH client) to generate a key and export it to this PC using SSH password-based auth (don't worry, I turned password-based auth back on before trying this) and got an "export failed" error. No further details.

It can't be something I'm doing. I did this exact process to set up key-based auth on an Ubuntu host and it worked fine. So I'm not sure if there's just something in Windows I have to change?

submitted by /u/FloatingMilkshake
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:)

 

key authentication

Quick poll! I finally got around to securing my remote VM by disabling password authentication and using key authentication only for SSH. Curious if others do the same.

 

key authentication

Key authentication is the recommended method for security, reject all password logins

If you lose the key use physical or remote console (IPMI)

 

key authentication

I actually recently switched to key authentication myself.