In this post I describe some of the settings and changes I made to make my Windows 10 and Ubuntu WSL into a fully fledged development environment. Here are the settings and tools I use for DevOps/SysOps on Windows.

The configurations and settings I describe here make that I can use tools like git, Ansible, Visual Studio Code, Testinfra and OpenSSH connections as good as possible in my Windows 11/10 workflow. All for Infrastructure as a Service (IaaS) :).


I have installed Microsoft Win32-OpenSSH (Win32 port of OpenSSH) Client for use with my Yubico YubiKey, as described in "How do I get my YubiKey to work with SSH in Windows 11 and Windows 10?". Before Win32-OpenSSH version I had to rely on Git Bash, which is a great tool, but made things more complicated for me (yet another ssh client installed, upgrade broke OpenSSH FIDO/U2F helper, and so on).

All ssh connections into the network need to go through a bastion host. I added a ProxyJump configuration to my Windows .ssh/config file:

Host  HostbasedKeyTypes,  Compression yes  User username  ForwardAgent yesHost *  ProxyJump  IdentityFile c:/users/username/.ssh/id_ed25519  IdentityFile /mnt/c/Users/username/.ssh/id_ed25519  User username  ForwardAgent yes

Once the connection with the bastionhost is created, I can continue using regular ED25519 keys. Here you also see an IdentityFile directive pointing to my Windows .ssh/id_ed25519 file using a Linux path. That is because I share OpenSSH keys with WSL in Windows 10. Doing so there is no need for having separate key files for Windows and Linux/WSL. Or is there?

Did you know you can tunnel RDP connections through SSH? This comes in very handy if your Windows Servers are behind a firewall or bastionhost.

Linux/WSL OpenSSH config

I found that, while working with Visuals Studio Code, git and Ansible/testinfra, it sometimes is more convenient to have a separate ssh config file for Linux/WSL. For example some actions I perform have to go through a SOCKS5 proxy, and I need a ProxyCommand without breaking my current ssh configuration. So I created an additional file: .ssh/wsl_config.

The munged ProxyCommand is:

Host *  ProxyCommand ncat.exe --proxy-type socks5 --proxy [::1]:4001 %h %p  User username  ForwardAgent yes

Notice the different top level domain extension ".net".

ncat.exe is the Windows netcat variant as found in nmap. You need to install this in Windows, not Linux/WSL. "Why no ProxyJump for this as well?", I hear you ask. Well, when I run Testinfra tests with ProxyJump, I have to log on (pad the YubiKey) multiple times per test. That sucks :)

To support YubiKey OTP authentication, I added the following to my .bashrc file to create an environment variable:

export SSH_SK_HELPER="/mnt/c/Program Files/OpenSSH/ssh-sk-helper.exe"

And the IdentityFile directive for my private keys:

Host  IdentityFile /mnt/c/Users/username/.ssh/id_ecdsa_sk_1  IdentityFile /mnt/c/Users/username/.ssh/id_ecdsa_sk_2  Compression yes  User username  ForwardAgent yes

If you've added this and try to log onto from within WSL, you notice the WinHello pop-up asking you to tap your YubiKey.

Touch your security key (in Dutch - sorry)

Sweet! :)

Reuse SSH connections

If you connect and disconnect a lot, for example you're git pull'ing various repos, or running Testinfra tests, might benefit from keeping a connection open and reusing it. Unfortunately OpenSSH directives like ControlMaster, ControlPath and ControlPersist are not supported in Windows. But they are in WSL.

Add to your .ssl/wsl_config file, under the Host directive it concerns:

Host  ControlMaster    auto  ControlPath   ~/tmp/%r@%h:%p.sock  ControlPersist 60s

Don't use ~/.ssh/ as your ControlPath if that folder is symlinked to Windows. For example if you share OpenSSH keys with WSL and Windows. Make sure ~/tmp exists.

ControlPersist 60s makes sure your connection will be kept open for at most 1 minute. Use ControlPersist Yes to keep it open until server will close the connection on its timeout.

Using this little piece of configuration prevents you having to touch / tap your YubiKey twenty times in a row while pulling in 20 repos or running multiple Testinfra tests, because you are reusing a single ssh connection. Neat :)

Keychain ssh-agent - Using SSH-Agent correctly in WSL 2

Partially taken from's post Using SSH-Agent the right way in Windows 10 WSL2.

Unfortunately you cannot integrate your Windows ssh-agent into WSL, and in WSL you'll notice an agent session does not persist when you open a new terminal window. Long story short, install and use the package keychain.

sudo apt-get install keychain

If necessary, you can edit your ~/.bashrc and add:

/usr/bin/keychain -q --nogui $HOME/.ssh/id_ecdsa_sk_1/usr/bin/keychain -q --nogui $HOME/.ssh/id_ecdsa_sk_2source $HOME/.keychain/$HOSTNAME-sh

When using -q there is no keychain greeting when you open a new shell. Note that this may not be necessary when you use Control* directives as shown above.


For various operations, for example to verify SSL/TLS certificates, test SMTP authentication over (Start)TLS connections, or to generate pseudo-random passwords, I need OpenSSL. In both Windows and WSL2 Linux.

Install OpenSSL in WSL2

Installing OpenSSL in WSL2 is just as easy as (assuming an apt distribution like Ubuntu):

sudo apt install openssl

Install OpenSSL in Windows

If your Windows system supports winget, installing OpenSSL is as easy as it is in WSL2. Just use winget:

winget search opensslwinget install ShiningLight.OpenSSL.Light# Or winget install ShiningLight.OpenSSL, depending on which # version / flavor you want.# # FireDaemon OpenSSL is now an option too:# winget install FireDaemon.OpenSSL

No winget? No worries! Follow these steps:

  1. Download Win32 OpenSSL Installation Project (choose the right flavor, this is the same OpenSSL as above)
  2. Install OpenSSL to -fo example- c:\OpenSSL-Win32 or c:\OpenSSL-Win64, depending on the bitness

Configure your Windows OpenSSL environment

Now configure your OpenSSL environment in Windows to prevent openssl.cnf warnings.

  1. at the cmd.exe command line, type set OPENSSL_CONF=c:\OpenSSL-Win64\bin\openssl.cfg. This will fix / resolve / prevent the following error message:

WARNING: can't open config file: /usr/local/ssl/openssl.cnf


GitHub Invertocat logo
GitHub Invertocat logo

My local code repos are in WSL, it's just easier. Why? Well, I started doing that since we had double colon (::) in file- and folder names in Puppet, something NTFS just won't understand. And running Testinfra tests from within Visual Studio Code requires having your repo there.

Git needs some TLC, because it has to work with your newly created WSL OpenSSH config. If you don't, git/WSL tries to use your Windows .ssh/config file, which lacks the ProxyCommand.

Add to your .bashrc file:

export GIT_SSH_COMMAND="ssh -F ~/.ssh/wsl_config"

This tells git to always use this specific ssh command, and the -F argument tells ssh to use this specific config file. Neat!


green and white snake illustration
Green Python

For Python I didn't have to make a lot of adjustments, only that I didn't want __pycache__ files everywhere / everytime. For this I added to .bashrc:


Ansible - configure an alternate SSH config file

Ansible in Windows 11 (or Windows 10) runs in Windows Subsystem for Linux, or WSL. You can apt install ansible and you're set. Using an alternative SSH config file with Ansible is something different.

As explained earlier, in WSL I use a different ssh config file, one specific for my WSL environment. Even though this is very handy in my workflow, it does take some time and trial & error to set everything up. Using Ansible (ansible-playbook) is one of those, so here is how you can configure and use a custom ssh config file with Ansible.

Ansible can use a custom ssh config file if you configure its ANSIBLE_SSH_ARGS environment variable. Add to your ~/.bashrc:

export ANSIBLE_SSH_ARGS="-F ~/.ssh/wsl_config"

This is almost the same Git GIT_SSH_COMMAND, except that this configures SSH arguments for Ansible. You can also run on your command prompt:

ANSIBLE_SSH_ARGS="-F ~/.ssh/wsl_config" ansible-playbook -i inventory/development playbooks/book.yml


With Testinfra you can write unit tests in Python to test actual state of your servers configured by management tools like Salt, Ansible, Puppet, Chef and so on. For use in Visual Studio Code, the path to py.test and pytest need to be known (e.g in the path environment variable):

export PATH="$PATH:~/.local/bin"

If you want to run a Testinfra test from within Visual Studio Code Remote, I found I have to provide the full path to my ssh config (--ssh-config=/home/username/.ssh/wsl_config) and prefix the hosts argument with ssh:// as protocol:

py.test --ssh-config=/home/username/.ssh/wsl_config --hosts="ssh://" -v --sudo 

This took some trial and error.


cloudmonkey ☁️? is a command line interface (CLI) for Apache CloudStack. CloudMonkey can be use both as an interactive shell and as a command line tool which simplifies Apache CloudStack configuration and management.

In (regular) Linux/Ubuntu you can install CloudMonkey using snap (snap is available by default in Ubuntu 16.04 and up):

$ sudo snap install cloudmonkey

But unfortunately, this doesn't work with WSL, as snap install fails. Luckily you can download standalone binaries and use CloudMonkey in Windows and Linux:

and this results in:

# WSL 2$ /bin/cmk versionApache CloudStack ? CloudMonkey 6.2.0
# WindowsPS C:\Users\janreilink> CloudStack ? CloudMonkey 6.2.0Report issues: cmk > versionApache CloudStack ? CloudMonkey 6.2.0(localcloud) cmk > exit


Packer, by HashiCorp, lets you create identical machine images for multiple platforms from a single source configuration. Just download the required .zip file and launch packer from your command line.

HashiCorp Packer in Windows PowerShell

Visual Studio Code

Visual Studio Code ("VS Code") is my editor / IDE of choice. It supports remote connections to Windows Subsystem for Linux (WSL). You can easiliy open a Linux/WSL folder using the command: code . (this opens up the current folder in Visual Studio Code).

You can use \\wsl$ as UNC path in Windows to access your Linux/WSL files from Windows Explorer.

VS Code Extensions

In VS Code, I have the following extensions installed:

Markdown text in Windows

For working with Markdown texts in Windows (creating, reading, organizing) I use both Obsidian and MarkText. Sadly, the latter seems to be no longer under active development, but be sure to check it out!

Conclusion and giveaway

In this post I showed you how you can turn Windows 11 and Windows 10 into a fully fledged development environment. It may take some getting used to, but if you're as shortcut-Ninja as I'm (I alt-tab, ctrl-c/ctrl-v a lot), you can work pretty fast in this set up. Just don't forget to run sudo apt update and sudo apt upgrade to keep Ubuntu updated.

Donate a cup of coffee
Donate a cup of coffee

Thank you very much! <3 ❤️


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