How to use Tailscale (wireguard based) mesh VPN to connect everything

What is Tailscale? It’s a mesh VPN based on the wireguard open source project. It’s a secure network to connect your own devices no matter where they are.

Tailscale is free to use with one account and up to 100 devices, which is enough to see how well this can work to connect up servers, storage and desktops. They have paid plans for teams and enterprise.

macOS and iOS

To start, download Tailscale on your Mac or iPhone then find your IP address. Once you are signed in and have your IP address you can connect easily between devices. For example, on your iPhone open the Tailscale app and see your installed devices. Click on your Mac and the IP will be copied into the clip board. Use this to connect with app such as Secure shellfish for SSH or VNC viewer for remote login. When you’re in the same network it’s impressive, but when you’re on a different network, separated far away, It’s magic.

The real test for me was to install Tailscale on some backup servers I manage to make it more secure and more convenient to access them. I had used a variety of remote control for business services and well, Tailscale is easier, quicker and much more awesome. All the other software I tried was much less awesome.

After using Tailscale mainly for remote control, I tested Tailscale to securely connect my remote Macs to my own MunkiReport server. I use Munki and MunkiReport to manage Macs and having Tailscale allows me to securely connect endpoints to the server without opening up ports on my router. MunkiReport allows me to detect malware (with DetectX plugin) or check on backup jobs with Archiware P5 backup software (using a module I wrote) or a multitude of other diagnostics such as disk space free, apps installed, and all kinds of great hardware and software metrics. So much reporting. And MunkiReport doesn’t need Munki specifically, so if Tailscale is installed for remote control why not report on everything else.

Synology DSM

Having Tailscale installed in all the Synology NAS I manage in various physical locations allows me to securely connect to all of these NAS from anywhere. With remote work using a NAS is a great way to sync data between locations. Synology has a lot of great built-in tools to make this happen and a very robust quick connect feature combined with ddns, and let’s encrypt certificates to support it. After setting up a few to sync one location to another I was constantly getting notifications of IPs being blocked on my firewall. I had to open a port on my firewall to let in the ssh / rsync traffic through and despite a strong set of firewall rules with a geo block there were still connection failures and password attempts. Using Tailscale I can now have a P5 server set up on one Synology NAS connecting to the Tailscale IP of other remote units and it can easily backup, sync or archive the data from the various locations.

To install the Synology Tailscale package check out this GitHub page. Download the app then side load it (manual install in package center). To enable it you will have to have ssh on, a user with permission to use it, and one command to type.

sudo tailscale up

In one case I didn’t have SSH enabled on the remote unit so I remoted into a Mac on the same network, enabled an admin user, turned on ssh with a time limit on the account, and then logged in. Once the above command is run you will get a link to a website to authenticate the device with your account.

Linux (CentOS)

I have also installed and tested Tailscale on a Linux (CentOS) storage server. In my case a Jellyfish which has a ZFS volume shared over direct 10GbE for Final Cut Pro video editors using nfs or smb. the Jellyfish works well on premise, but wouldn’t it be nice to capture camera cards to the remote storage server via Tailscale? Oh yes it would. And what about playing back some of the video files via VLC on your iPhone! Or Files.app! Yes, to all the above. All made possible with Tailscale. And a huge shout out for their great documentation. Installing Tailscale on CentOS was super simple. Add a yum repo, install, tailscale, and then bring the service up. Couldn’t be easier.

sudo yum-config-manager --add-repo https://pkgs.tailscale.com/stable/centos/7/tailscale.repo

sudo yum install tailscale

Shared Devices

A small, but very exciting, feature was added part way through my testing of Tailscale which made it infinitely more awesome, shared devices. The concept is you are authenticated to your devices and can see in the Tailscale app all the IPs to connect to, but what if you could share one device (computer, server, NAS) with another person? Well, now you can. In the Tailscale admin console choose a device and send a share link to someone, they then will see this devices in their device list as shared. Home users can set up Tailscale to access all their own devices, but now can also choose to share access with a device in particular. For example, if you create an account, open a service (file sharing) and send a share link then the other person will login with the account you create and access the one thing you want them to. Maybe it’s a smb share to drop files. Works great for video collaboration and other kinds of teams.

There’s a whole lot more you can do with Tailscale (and wireguard) mesh VPN but I hope this gives you all some ideas to start with.