Apple, Computers, Hardware, Linux, Software, Windows

Using Synergy Over VPN

I’ve been watching a lot of Linus on Tech and one of their sponsors sells a product called Synergy. More information on their product page: . To summarize, this is a software KVM (no video, so I guess it is “KM”?) solution. The use case was perfect for me. On my desk I have an Apple work laptop, a Windows desktop, and a Linux personal laptop. Anyone that has done extensive work on a laptop keyboard and touchpad know that it isn’t optimal. I didn’t want multiple keyboards and mice on top of my desk because of the clutter. I dropped some money for Synergy, and it just works!


That is until I had to connect to our company VPN the next week. They use a full tunneling solution. When I connect, I lose everything. I can’t print, I can’t access my NAS, but most importantly I can’t access my keyboard and mouse. (The video is fine because it is a hard wire to an external monitor). What to do?

SSH to the rescue! What is SSH? This is a protocol that will allow one computer to securely interface with another computer. Secure SHell. However, we will just be using it for port forwarding, and not for an interactive session. The goal is to take the OS X machine (Synergy client), and SSH into the Windows server (Synergy server). Using this SSH connection, we can forward ports within it. It is a tunnel running inside the SSH connection. This will expose a local port on OS X for 24800 that is actually pointing to the remote server port 24800. This is the port that Synergy uses for its connections.

You will need a few tools, and a little patience. Having just gone through this, I’m sharing for posterity, or maybe for anyone that has thrown in the towel with how crippled VPN makes accessing home devices.

I have the following Synergy setup:

  • Windows 10 Synergy server (keyboard and mouse are physically connected to the desktop)
  • OS X Synergy Client
  • Linux Synergy Client
  • Router with a local area network all these devices share
  • Admin access to the router for port forwarding
  • Autossh package for OS X (available via brew)

First step, get Windows 10 up to speed with SSH. How this isn’t built in as a service in the year 2017 I have no idea. Grab the OpenSSH server package for Windows from . After downloading, extract and run the setup file. This will create a new Windows service for OpenSSH that will run on port 22. It prompts you to generate an SSH key for the server.

Once this server is running, you will need to add your user to the list of SSH users. Open up PowerShell as an administrator and change into the C:\Program Files\OpenSSH\bin directory. Run the following commands:

mkgroup -l >> ..\etc\group
mkpasswd -l >> ..\etc\passwd

Try and connect to your SSH server from the OS X client:

ssh <user>@<server IP> # e.g. ssh Ben@

You should be prompted for your Windows password. Once you can successfully login to the server, we can setup public key authentication. This removes the need for you to type in your password because you identify yourself with an SSH public key. From your OS X machine get your public key:

cat ~/.ssh/

Put the contents of this file on your SSH server in the file C:\Program Files\OpenSSH\home\<user>.ssh . This is actually a symlink to C:\Users\<user>.ssh . If the directory .ssh doesn’t exist, you will need to create it first. Now we need to configure the server to allow public key authentication. Edit the C:\Program Files\OpenSSH\etc\sshd_config file and change the following lines:

StrictModes no
PubkeyAuthentication yes
AuthorizedKeysFile .ssh/authorized_keys

Restart the OpenSSH server for the changes to take effect:

net stop opensshd
net start opensshd

You should now be able to SSH into the server same as before but without being prompted for a password.

Now we are ready to create an SSH tunnel. Before we incorporate AutoSSH (which handles retries and monitoring) we will do a naive attempt to SSH. In the following command:

  • -f backgrounds the process
  • -L does port tunneling in the format of <local port>:<remote host>:<remote port>
  • -N do not run a command – just tunnel the port
ssh -f <user>@<remote public IP> -L 24800:<remote public IP>:24800 -N

If this works, you should see a [LISTEN] entry for port 24800 when you list open files:

lsof -n -i | grep 24800

You may need to set your server as the DMZ on your network. Or to be safer you can simply setup port forwarding. We will need port 22 and port 24800 to resolve to the Windows server. The instructions for how to do this on a router widely vary by vendor. Typically it is under a WAN section. It typically prompts for a port, a destination IP, and destination port, and protocol. You want ports 22 and 24800 to route to your server IP for TCP and UDP.

Configure your Synergy client to use localhost instead of the remote IP. You should now be able to operate your client from the server’s peripherals via Synergy.

Everything works great until the VPN connection is made. The reason is that the SSH connection is severed. In order to recover automatically, I have added autossh to persist this tunnel. On the OS X client instead of running SSH do the following:

AUTOSSH_POLL=10 autossh -M 20000 -f -N <user>@<remote public IP> -L 24800:<remote public IP>:24800

Now when a VPN connection is made, or a disconnection happens, the autossh package will detect that it is no longer alive and retry. Because Synergy’s software also retries, after a few seconds your connectivity should begin working again.

Thanks to Synergy for making a solid product, and for having first class Linux support.


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