Nicholas Clooney

A Short Guide to Tailscale: Secure Networking Made Simple

Over the past few weeks, I’ve spent quite a bit of time experimenting with Tailscale, and it has quickly become one of my favorite tools.

If you haven’t heard of it, Tailscale is a secure, easy-to-use mesh VPN built on WireGuard. It lets your devices talk to each other as if they were on the same local network, no matter where in the world they are.

I originally wrote about my broader Tailscale journey in previous blog posts (Coding on iPhone Anywhere, Network Debugging Deep Dive), but this time I want to focus on something more concrete: a starter guide mixed with a few real-world examples of how I personally use it — from helping my family in China to keeping my own services private.

Table of Contents

Why Tailscale?

For most people, a VPN means either the clunky corporate tool you log into for work, or a consumer VPN app that promises “privacy” while routing all your traffic through someone else’s servers. Both feel like a black box — you don’t really know what’s happening behind the scenes.

Tailscale is different. It gives you your own secure private network and complete control. Just install the app, log in with an account (Google, Apple, GitHub, etc.), and suddenly all your devices can see each other as if they were side by side.

Here’s why I love it:

  • Simple setup — No need for port forwarding or manual network rules.
  • Security baked in — WireGuard under the hood with identity-based authentication.
  • Cross-platform — Works on macOS, iOS, Linux, Windows, Android, even routers.
  • Feels like one network — With MagicDNS (enabled by default now), you can connect to devices by name instead of remembering IPs, i.e. ssh debian/macbook-pro/macbook-air.

And here’s the powerful part:

  • You can access your laptop from anywhere in the world as though it’s on the same Wi-Fi.
  • You can set an exit node to proxy all your traffic through another location — useful for bypassing firewalls, avoiding restrictions, or just browsing as if you’re back home.
  • You can run private services safely without ever exposing them to the public internet.

Getting Started

If you’re new to Tailscale, here’s the fastest way to dive in:

  1. Sign up with your preferred login (Google, Apple, GitHub, etc.).
  2. Install Tailscale on your devices — laptops, phones, servers.
  3. Log in, and you’ll see them appear in your personal tailnet.
  4. Test it out — SSH into another machine, or open a private service through its Tailscale address.

That’s it. No firewall rules. No public IP headaches. Just devices talking directly and securely.

Real-World Examples of Tailscale in Action

Helping Family Across the Great Firewall

One of the most meaningful use cases for me has been setting up Tailscale for my family in China. It lets them connect to the open internet in a secure and reliable way, without needing to wrestle with traditional VPN software. For them, it’s just an app they open — and suddenly they’re connected.

I love and enjoy the moment when they realized how easy it is to set up and how powerful it is to provide a free internet with that little effort.

My Own Private Remote Terminal

Tailscale also powers my own workflow. Whether I’m hopping between my MacBook Air and MacBook Pro, or connecting into a remote server, it acts as my secure remote terminal solution. It feels like SSH over a local network, even though I might be halfway across the world.

And the best thing is? I don't even have to expose the SSH port for it at all!

Secure Access to My Own Services

I run a few private services — like my blog's preview on my MacBook Pro or an analytics dashboard on a personal server. Instead of exposing them to the public internet, I keep them locked down behind Tailscale. That way, they’re only accessible to me (or whoever I explicitly share them with). It’s peace of mind, without sacrificing convenience.

Tips and Extras

Once you’re comfortable, there are some great extras worth exploring:

  • Exit nodes — Route your internet traffic through another device when you need it (like using your home connection from abroad).
  • Tailscale Send — Transfer files directly between devices.
  • Sharing — Give family or teammates access to a specific device or service without opening everything.

Closing Thoughts

For me, Tailscale isn’t just another networking tool. It’s a solution I enjoy using — simple, secure, and quietly powerful. Whether I’m helping my family stay connected, accessing my own servers, or keeping services private, it’s become part of my daily workflow.

If you’ve ever felt frustrated by traditional VPNs, I highly recommend giving Tailscale a try. And if you’re curious about the longer story of how I got here, you can read my earlier post about my full Tailscale journey.

Have you used Tailscale in your own setup? I’d love to hear about your experiences.