I love the persistence of a host machine! I’m too cheap to get a VPS. I really like the windows 11 OS but really love mac laptops. I left 3389 open on my router (with DDNS) and found myself getting brute forced. I saw this post around the same time, and realized tunnelling could be a great alternative.


General Assumptions

I wrote this for my situation. While setting it up, I found there was not a central guide, so I made one. If it doesn’t perfectly fit your situation, hopefully a part of it will help.

Assumptions About You

  • You have administrator access to both machines
  • You are comfortable with the command line on both systems
  • You have VSCode installed on both machines
  • You’re aware of the concept of SSH
  • You have a Cloudflare account and a website there
  • You’re using brew

Assumptions About This Guide

  • I’ve got example.com on my cloudflare account (I don’t, obvs)
  • My tunnel is named wormhole
  • My tunnel id is 123455677890asdf
  • My macOS username is me

Host Setup

Windows Setup

  1. get pwsh (i used winget)

    PS> winget install Microsoft.PowerShell
    • At the time of writing, should be v7.2
  2. install chocolatey at https://chocolatey.org/

    PS> Set-ExecutionPolicy Bypass -Scope Process -Force [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))
  3. install cloudflared via chocolatey

    PS> choco install cloudflared
  4. login
    PS> cloudflared login
    • you may need to manually open the link in the output and select the site you’d like to add the tunnel to
  5. create a tunnel
    PS> cloudflared tunnel create wormhole
  6. setup cloudflared as a service
    PS> cloudflared service install
    PS> mkdir C:\Windows\System32\config\systemprofile\.cloudflared
  7. create a config
    PS> code C:\Windows\System32\config\systemprofile\.cloudflared\config.yml
    • example:
    tunnel: 123455677890asdf
    credentials-file: C:\Windows\System32\config\systemprofile\.cloudflared\123455677890asdf.json
        - hostname: wormhole.example.com
        service: ssh://localhost:22
        - service: http_status:404
  8. set service as automatic

    PS> Set-Service -Name Cloudflared -StartupType "Automatic"
    PS> Set-ItemProperty HKLM:\SYSTEM\CurrentControlSet\Services\Cloudflared\ -Name ImagePath -Value "C:\ProgramData\chocolatey\lib\cloudflared\tools\cloudflared.exe --config=C:\Windows\System32\config\systemprofile\.cloudflared\config.yml tunnel run"
    PS> cloudflared tunnel route dns  wormhole.example
  9. add a non-admin user (for ssh only). enter a paasword when prompted

    PS> New-LocalUser -Name me-ssh
  10. set pwsh as your default shell

    PS> New-ItemProperty -Path "HKLM:\SOFTWARE\OpenSSH" -Name DefaultShell -Value "C:\Program Files\PowerShell\7\pwsh.exe" -PropertyType String -Force
  11. create external user .ssh directory to house authorized_keys

    PS> mkdir C:\Users\me-ssh\.ssh
  12. modify sshd_config

    PS> code C:\ProgramData\ssh\sshd_config
    • enable publickey authentication, uncomment this line
    PubkeyAuthentication yes
  13. setup sshd & ssh-agent as automatic services, and start them

    PS> Set-Service -Name sshd -StartupType "Automatic"; Set-Service -Name ssh-agent -StartupType "Automatic"; Start-Service sshd; Start-Service ssh-agent

Client Config


  1. make sure developer tools are up to date

    $> brew install cloudflare/cloudflare/cloudflared
    • to confirm install
    $> cloudflared -v
  2. Login (just like on the host setup)
    $> cloudflared login
    • A browser window should have opened.

    • If the browser failed to open, please visit the output URL directly in your browser.

  3. Select the site you want to to log in to
    • after selecting you’ll see in the terminal
     You have successfully logged in.
     If you wish to copy your credentials to a server, they have been saved to:
  4. next, update your hosts file
    $> code ~/.ssh/config
    • add the following
    Host *.example.com
        ProxyCommand /usr/local/bin/cloudflared access ssh --hostname %h
  5. now you can ssh into the box directly
  6. But let’s take this further for RDP and setup local forwarding

     $> ssh -L 56789: [email protected]
  7. Setup pub key and add to host
     cat ./.ssh/id_rsa.pub | ssh [email protected] "echo | Out-File -FilePath ~/.ssh/authorized_keys -Append"

Further thoughts

  • Connect to the tunnel from the client machine on startup https://mpharrigan.com/2016/05/17/background-ssh.html
  • Remove the password from the newly created user
  • Change default ports (ssh, RDP)
  • Restrict RDP access to only
  • Create a host and client scripts to just take care of all of this