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I'm doing quite trivial task. I'm trying to connect to Windows 10 machine from Ubuntu through SSH. OpenSSH is installed on machines and it's up and running. I can SSH into my Raspberry Pi without a problem, but when I try to execute ssh -p22 user@internal_ip from Ubuntu to Windows I get port 22: Connection timed out. When I try the other way around ... to connect from Windows to Ubuntu I get connection refused. I checked the firewall on both machines and it's set up to allow port 22. All computers are on the same network. And VPN is switched off. I can SSH into my instance on AWS but can't on my local machines ???

What I might've missed ? Is there any setting I should check ?

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  • How did you install OpenSSH on Windows? Can you verify, via Computer Management --> Services and Applications, that both OpenSSH services are running? Also, post your c:\ProgramData\ssh\sshd_config.
    – ajgringo619
    Commented Jan 3, 2020 at 20:07
  • Ohh gosh .... I checked the running services in Computer Management --> Services and Applications as you mentioned only to find out that I did install the service but it wasn't running. When you install OpenSSH on Ubuntu it installs it and runs it by default but on W10 one needs to launch it manually. Didn't know that. I can now SSH into it. Feel free to post it as an answer and I'm gonna tick it for you.
    – mark
    Commented Jan 3, 2020 at 20:27

1 Answer 1

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For whatever reason, the default installation of OpenSSH on Windows 10 does not automatically start the service. Change the startup type of OpenSSH SSH Server to Automatic; if you're using public-key authentication, you'll also need to enable OpenSSH Authentication Agent.

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