Scott Hanselman

How to use Windows 10's built-in OpenSSH to automatically SSH into a remote Linux machine

January 23, 2019 Comment on this post [6] Posted in DotNetCore | Hardware | Open Source
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In working on getting Remote debugging with VS Code on Windows to a Raspberry Pi using .NET Core on ARM in my last post, I was looking for optimizations and realized that I was using plink/putty for my SSH tunnel. Putty is one of those tools that we (as developers) often take for granted, but ideally I could do stuff like this without installing yet another tool. Being able to use out of the box tools has a lot of value.

A friend pointed out this part where I'm using plink.exe to ssh into the remote Linux machine to launch the VS Debugger:

"pipeTransport": {
"pipeCwd": "${workspaceFolder}",
"pipeProgram": "${env:ChocolateyInstall}\\bin\\PLINK.EXE",
"pipeArgs": [
"debuggerPath": "/home/pi/vsdbg/vsdbg"

I could use Linux/bash that's built into Windows 10 for years now. As you may know, Windows 10 can run many Linuxes out of the box. If I have a Linux distro configured, I can call Linux commands locally from CMD or PowerShell. For example, here you see I have three Linuxes and one is the default. I can call "wsl" and any command line is passed in.

C:\Users\scott> wslconfig /l
Windows Subsystem for Linux Distributions:
Ubuntu-18.04 (Default)
C:\Users\scott> wsl ls ~/
forablog forablog.2 myopenaps notreal test.txt

So theoretically I could "wsl ssh" and use that Linux's ssh, but again, requires setup and it's a little silly. Windows 10 now supports OpenSSL already!

Open an admin PowerShell to see if you have it installed. Here I have the client software installed but not the server.

PS> Get-WindowsCapability -Online | ? Name -like 'OpenSSH*'

Name : OpenSSH.Client~~~~
State : Installed

Name : OpenSSH.Server~~~~
State : NotPresent

You can then add the client (or server) with this one-time command:

Add-WindowsCapability -Online -Name OpenSSH.Client~~~~

You'll get all the standard OpenSSH stuff that one would want.

OpenSSL tools on Windows

Let's say now that I want to be able to ssh (shoosh!) into a remote Linux machine using PGP keys rather than with a password. It's much more convenient and secure. I'll be ssh'ing with my Windows SSH into a remote Linux machine. You can see where ssh is installed:

C:\Users\scott>where ssh

Level set - What are we doing and what are we trying to accomplish?

I want to be able to type "ssh pi@crowpi" from my Windows machine and automatically be logged in.

I will

  • Make a key on my Window machine. The FROM. I want to ssh FROM here TO the Linux machine.
  • Tell the Linux machine (by transferring it over) about the public piece of my key and add it to a specific user's allowed_keys.

Here's what I did. Note you can do this is several ways. You can gen the key on the Linux side and scp it over, you can use a custom key and give it a filename, you can use a password as you like. Just get the essence right.

Below, note that when the command line is C:\ I'm on Windows and when it's $ I'm on the remote Linux machine/Raspberry Pi.

  • gen the key on Windows with ssh-keygen
  • I ssh'ed over to Linux and note I'm prompted for a password, as expected.
  • I "ls" to see that I have a .ssh/ folder. Cool. You can see authorized_keys is in there, you may or may no have this file or folder. Make the ~/.ssh folder if you don't.
  • Exit out. I'm in Windows now.
  • Look closely here. I'm "scott" on Windows so my public key is in c:\users\scott\.ssh\ Yours could be in a file you named earlier, be conscious.
    • I'm type'ing (cat on Linux is type on Windows) that text file out and piping it into SSH where I login that remote machine with the user pi and I then cat (on the Linux side now) and append >> that text to the .ssh/authorized_keys folder. The ~ folder is implied but could be added if you like.
  • Now when I ssh pi@crowpi I should NOT be prompted for a password.

Here's the whole thing.

C:\Users\scott\Desktop> ssh-keygen
Generating public/private rsa key pair.
Enter file in which to save the key (C:\Users\scott/.ssh/id_rsa):
Enter passphrase (empty for no passphrase):
Enter same passphrase again:
Your identification has been saved in C:\Users\scott/.ssh/id_rsa.
Your public key has been saved in C:\Users\scott/.ssh/
The key fingerprint is:
The key's randomart image is:
+---[RSA 2048]----+
| . .... . |
|..+. .=+=. o |
| .. |
C:\Users\scott\Desktop> ssh pi@crowpi
pi@crowpi's password:
Linux crowpi 2018 armv7l

pi@crowpi:~ $ ls .ssh/
authorized_keys id_rsa known_hosts
pi@crowpi:~ $ exit
Connection to crowpi closed.
C:\Users\scott\Desktop> type C:\Users\scott\.ssh\ | ssh pi@crowpi 'cat >> .ssh/authorized_keys'
pi@crowpi's password:
C:\Users\scott\Desktop> ssh pi@crowpi
pi@crowpi: ~ $

Fab. At this point I could go BACK to my Windows' Visual Studio Code launch.json and simplify it to NOT use Plink/Putty and just use ssh and the ssh key management that's included with Windows.

"pipeTransport": {
"pipeCwd": "${workspaceFolder}",
"pipeProgram": "ssh",
"pipeArgs": [
"debuggerPath": "/home/pi/vsdbg/vsdbg"


NOTE: In my previous blog post some folks noted I am logging in as "root." That's an artifact of the way that .NET Core is accessing the GPIO pins. That won't be like that forever.

Thoughts? I hope this helps someone.

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About Scott

Scott Hanselman is a former professor, former Chief Architect in finance, now speaker, consultant, father, diabetic, and Microsoft employee. He is a failed stand-up comic, a cornrower, and a book author.

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January 25, 2019 10:54
Don't mess around creating the .ssh folder on the remote machine by hand. Use ssh-copy-id from your desktop instead, it does everything for you, and you can rely on the same syntax whether you're SSHing from Windows or Linux.
January 25, 2019 11:59
It's a little shameless plug, but it's relevant. I recently wrote about how I ssh'd into GitHub (as I'd never done that before). It also contains the pitfalls I fell into when creating my first keys. May not have done the best job, but it's the first time I did that.
January 25, 2019 12:45
Windows doesn’t have ssh-copy-is yet
January 26, 2019 12:58
If you have to create the .ssh directory and authorized_keys file, make sure to set the right permissions.

Create the .ssh directory:

mkdir ~/.ssh

Set the right permissions:

chmod 700 ~/.ssh

Create the authorized_keys file:

touch ~/.ssh/authorized_keys

Set the right permissions:

chmod 600 ~/.ssh/authorized_keys

The permissions are important! It won't work without the right permissions!

Bonus mission: make smart use of the ssh config file on your FROM machine. Create the file
and make sure it has no extension. You can store your important remote machines like this
## Raspberry PI ##
Host raspi
User pi
#Port 12345

The hostname resolution is slow in my network, so I used the IP directly (which is fixed in my router settings). Now you can

c:\users\scott> ssh raspi

Enjoy :o)
January 29, 2019 3:45
This line:
C:\Users\scott\Desktop> type C:\Users\scott\.ssh\ | ssh pi@crowpi 'cat >> .ssh/authorized_keys'
...just blew my mind. That's some next-level SSHing right there!
January 29, 2019 13:11
...and just like that I can now SSH all over my home network with nary a password prompt. Also, the Ubiquiti UniFi cloud key lets you paste in the contents of your public key file in the config, and it takes care of provisioning it out to all of its managed network devices for you.

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Disclaimer: The opinions expressed herein are my own personal opinions and do not represent my employer's view in any way.