The Deep Dive: Ditching Tailscale for Raw WireGuard

You know, there’s a certain thrill in taking something that just works and tearing it down to understand its inner workings. For a while now, I’ve been happily using Tailscale, a fantastic VPN solution built on the WireGuard protocol. It’s brilliant, truly, simplifying network access to an almost absurd degree. But a little voice in the back of my head kept whispering, “What’s really happening under the hood? Could I do this myself?” So, I decided to take the plunge: a full month running a raw WireGuard setup, no Tailscale magic, just me and the command line. And let me tell you, it was an eye-opener.

My initial motivation wasn't about dissatisfaction with Tailscale; quite the opposite. It was about pure curiosity and a desire to deepen my understanding of networking. Tailscale abstracts so much away – the NAT traversal, the key management, the identity-based access control. It’s wonderful for most people, but for someone like me who loves to tinker, it felt like a black box I just had to peek inside. Plus, the idea of having complete, granular control over my VPN, without any third-party control plane, had a certain allure. Call it a quest for simplicity through complexity, if you will.

Diving into the setup process for raw WireGuard, you quickly realize where Tailscale earns its stripes. The first step was getting a server configured. I installed `wireguard-tools`, generated my public and private keys (a crucial pair for both server and clients), and then began crafting the `wg0.conf` file. This wasn't just about IP addresses; it involved defining the server’s VPN IP, its listening port, and, critically, `PostUp` and `PostDown` scripts. These scripts, if you’re unfamiliar, are essential for telling the server how to handle traffic forwarding and setting up firewall rules (I used UFW). Suddenly, I was dealing with `net.ipv4.ip_forward` and `iptables` rules directly. It felt powerful, yes, but also a bit like walking a tightrope.

Then came the clients. Each device – my laptop, my phone, another server – needed its own key pair and its own `wg0.conf` file. This is where the manual overhead really starts to bite. You’ve got to specify the server’s public key, its external endpoint (that’s the public IP address and port), and, crucially, the `AllowedIPs`. This last one was a subtle beast. If I just wanted to access the server itself, it was straightforward. But if I wanted clients to reach other devices on the server’s local network (a subnet, essentially), I had to explicitly list that entire subnet in the `AllowedIPs` for each client. And, of course, ensure the server was correctly configured to route that traffic. It quickly became clear that scale here would be a nightmare compared to Tailscale's automated approach.

One of the biggest hurdles, and frankly, where Tailscale truly shines, was handling NAT traversal. In a typical home setup, your router provides Network Address Translation (NAT), giving all your internal devices private IP addresses while presenting one public IP to the internet. If that public IP is dynamic (which it often is), and you're behind CGNAT, things get even trickier. Tailscale effortlessly navigates this with its DERP relays, essentially bouncing traffic through a public relay when a direct connection isn’t possible. With raw WireGuard? Nope. I had to set up dynamic DNS (DuckDNS, in my case) to track my ever-changing public IP, and then painstakingly configure port forwarding on my router. Every time my public IP changed, I had to manually update the `Endpoint` in all of my client configurations, or at least rely on a script to do it. It was a stark reminder of the conveniences I’d taken for granted.

After a month of this hands-on, sometimes frustrating, often enlightening experience, what’s the verdict? Well, Tailscale is absolutely phenomenal for its sheer ease of use and its intelligent handling of network complexities. For 99% of users, it’s simply the better choice. It manages keys, handles dynamic IPs, sets up subnet routing, and offers identity-based access control – all with minimal fuss. It’s like having a team of network engineers working tirelessly in the background.

However, running raw WireGuard wasn't without its merits. The sense of control is unmatched. I understood every byte, every rule, every connection. It forced me to learn about `iptables`, IP forwarding, and the intricacies of `AllowedIPs` in a way that theoretical reading never could. For someone who thrives on understanding infrastructure at a deeper level, or for specific use cases where you need absolute minimal dependencies and complete self-sufficiency (think dedicated servers with static IPs), raw WireGuard is incredibly powerful and efficient. It's lean, it's fast, and it works exactly how you tell it to.

So, did I ditch Tailscale forever? Not entirely. I appreciate its genius even more now. For my daily drivers and devices that move around a lot, Tailscale is back. But for my fixed server setups, where I crave that fine-grained control and a deeper understanding, raw WireGuard now has a firm place. This month-long experiment was less about finding a "replacement" and more about education. It lifted the veil, showing me just how much sophisticated engineering goes into making complex networking feel simple. And honestly, that understanding is priceless.