Tailscale vs WireGuard on Raspberry Pi: Which VPN Should You Use?

WireGuard and Tailscale are popular VPN servers that you can self-host on your Raspberry Pi. They sound similar at first glance, both being free and even using the same protocol, but which one should you run? I’ll help you understand the differences in simple terms.

WireGuard is a traditional VPN server, whereas Tailscale is a mesh-style VPN solution. With WireGuard, the user has full control and can customize every aspect of the server. Tailscale, on the other hand, is a managed solution where configurations are set for the user.

Let’s start with a brief overview of how they work, and then we’ll go over the key differences between them. By the end, you should have a good idea of which VPN solution fits your needs best.

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Overview: What’s the Difference Between Tailscale and WireGuard?

Hosting a VPN server gives you a secure way to access your home network over the internet, wherever you are.

For example, if you’re on a laptop in another state, you can connect via VPN to your Raspberry Pi, and you’ll have access to everything as if you were physically there. That lets you do things like transfer files from a NAS on your network, even though it’s secured for local use only.

WireGuard and Tailscale are both excellent VPN servers for this purpose.
Let me give you a quick introduction to each one.

WireGuard

The modern VPN protocol.

In the olden days, the traditional way to do things would be to self-host a VPN server with OpenVPN. Today, WireGuard is the newer and faster VPN protocol. It’s written to be more performant and easier to configure than OpenVPN.

Connecting to WireGuard works just like a typical client-server model you’re probably familiar with: your client device connects to your Pi VPN, and traffic routes through that server to wherever you want to go.

WireGuard is a free and open-source VPN you can self-host. You can run the server on a Raspberry Pi and be in charge of everything, so you completely control privacy and security.

Tailscale

A mesh VPN built on top of WireGuard.

Even though WireGuard has made VPN servers more modern and convenient, there’s still a lot to configure if you want to add advanced functionality. That’s where Tailscale comes in.

Tailscale is another VPN server that you can run on your Raspberry Pi. It’s actually built using the WireGuard protocol as its base, but it gives you a graphical frontend that makes it easier to set up.

Instead of a traditional server model, Tailscale creates a peer-to-peer (P2P) mesh network. Any device on your “Tailnet” can talk directly to each other using encrypted tunnels.

For instance, a PC in France and a laptop in the USA, if they’re both connected to the Tailnet, would both see each other as peers on the same local network.

The Tailscale server resides on your Raspberry Pi, but it’s a commercially managed service. That means you have to create an account on the company’s website to use it.

Key Differences: Tailscale vs. Wireguard

Now that you understand that WireGuard and Tailscale are both VPN servers that can be hosted on a Raspberry Pi, let’s go over the implications of these differences and why you might choose one over the other.

Raspberry Pi Support

The first question you might have is whether the Raspberry Pi model you have can run it:

• WireGuard can be installed on any mainline Raspberry Pi board.
• Tailscale is only supported on more recent models.

Here’s a quick summary of which boards are supported by each:

WireGuard	Tailscale
Raspberry Pi Zero Raspberry Pi 1 Raspberry Pi 2 Raspberry Pi 3	Raspberry Pi Zero 2W
Raspberry Pi 3B+ Raspberry Pi 4 Raspberry Pi 5	Raspberry Pi 3B+ Raspberry Pi 4 Raspberry Pi 5

There are also differences in which operating systems the server can be installed on. Both support Raspberry Pi OS; WireGuard supports niche systems like DietPi, whereas Tailscale supports a wider variety of distributions.

Separate from the server, however, both WireGuard and Tailscale have client apps to connect every device you can think of: Windows, Android/iOS, Red Hat, Synology DSM, and many more.

Ease of Installation

Sometimes choosing a software solution isn’t determined by how superior the technology is, but by how much work you’ll have to put into maintaining it, and whether it’s worth the effort. Let’s go over which VPN server is easier to set up.

WireGuard Installation

To install WireGuard on Raspberry Pi, most people will use a setup script specifically made for it.

The script asks a lot of questions to configure things, but you can just hit ENTER over and over to accept the defaults until the installer is finished.

To add a client to your VPN server, you must generate a configuration file for each device and transfer that file to the device. Or, much easier for me was to generate a QR code to add to my phone or tablet.

For more detailed instructions, check out the tutorial we wrote for WireGuard below:
WireGuard Installation on Raspberry Pi: Easy Setup Guide.

Tailscale Installation

Installing Tailscale on a Raspberry Pi was about just as easy.
You add a custom repo, install the Tailscale package, and bring the service up:

From there, you log in to the Tailscale website and link your Raspberry Pi to their service.

The site will handhold you through connecting clients to your VPN, from providing the IP address to use to even specific instructions for different types of devices.

For more detailed instructions, check out the guide we wrote for Tailscale below:
Tailscale VPN Setup on Raspberry Pi: Secure Home Networking

Verdict

So which one was easier to set up?

Both software were easy to install with minor points of friction. For instance, Tailscale requires authentication via one of its approved identity providers, and I wasn’t sure if I wanted to give my Google login or Apple ID.

WireGuard requires additional networking steps, such as adding a port-forwarding rule on the router, as well as transferring the configuration file to every client device.

Overall, Tailscale requires fewer steps for installation. You log in to the site on a client device, and you’re connected to your Pi VPN. From the dashboard, you can invite other users via email and have them approved to connect just like that.

Privacy

One of the key reasons I use a VPN is to protect sensitive data on my devices, so privacy is high up on my priority list.

With WireGuard, you get full privacy. The traffic moves encrypted between your client devices (e.g. laptop or phone) and your VPN server (Raspberry Pi).

Tailscale, on the other hand, is a managed service run by a for-profit corporation. You can peruse their privacy policy (does anybody actually read all of it?), where they say that what information they keep about you is minimal.

With any software where your data goes through a third party, however, there’s no guarantee that any of your information won’t be collected later or stolen from a data breach.

I think WireGuard wins here by design.

Security

With WireGuard, you have to be on top of security by yourself. It relies on cryptographic keys for authentication, which are secure, but you have to ensure you manage these keys for multiple users and devices.

By default, access to the VPN is all or nothing. So if you have network resources you want to protect in case an intruder breaks in, you should define firewall rules for that.

If you’re careful and know what you’re doing, WireGuard is lean and secure. Since every device and every feature has to be purposefully configured one by one, it’s more difficult for you to accidentally make the server wide open to attack.

The other side of this argument is that perhaps users don’t exactly know what they’re doing in terms of security. So Tailscale tries to make up for user error, for instance, by giving you a graphical dashboard that makes it easy to control how keys are issued or revoked. You can also create Access Control Lists to limit which users can access what on the network.

An “it-just-works” design means you can also easily flip a switch on the dashboard that you didn’t realize was unsafe. One might also argue that since so many VPNs go through Tailscale, it makes the company a juicy target for bad actors.

This one’s a close call: which VPN server you feel safer with will depend on your knowledge and comfort level. Those with more networking expertise may feel that WireGuard is more secure, and those with limited knowledge will probably feel safer with Tailscale.

Cost

WireGuard is FOSS, which means that it’s free indefinitely. It follows everything we love about the Linux open-source philosophy, and the WireGuard protocol is now incorporated into the Linux kernel itself.

Tailscale, on the other hand, is a proprietary service. It offers a free tier, but it limits the number of unique users that you can have on your VPN. To connect more users, you’ll have to upgrade to a paid subscription tier.

Tailscale’s free tier for personal use is quite generous, but if the company gets sold, what happens to your setup or your data? These fears haven’t come true yet, but these are issues to consider when planning for the long term.

For the average home user who might be using a VPN just for themselves or for a small family, both WireGuard and Tailscale are on par here (free).

However, if you’ll be hosting lots of users on your VPN, then there’s a calculation to make. WireGuard will cost zero, not counting the time you put in to maintain it. But if you’re running a business and want uptime to be almost guaranteed at all times, then Tailscale might be worth a paid subscription.

Features

Besides an encrypted connection, which VPN server comes with extra features that you want?

Tailscale offers more features out of the box: magic DNS, Tailscale funnels, Mullvad integration, ACLs, and SSH session recording—just browsing through the dashboard with all of the possible settings can be overwhelming.

Many also consider Tailscale to be a more scalable solution. Every new device you add automatically joins your mesh, instantly connecting to all others. You can even turn your laptop into a gateway, so you can access other devices on a network that might not even have Tailscale.

WireGuard doesn’t look as fancy or have as many features out of the box, but there are some benefits to a lean approach. For one, you’re allowed to customize everything for your VPN setup, from the ports to the routing rules. This matters if you need to configure your VPN for:

• Performance tweaks.
• Specific security concerns.
• Making it compatible with a second VPN provider or other software like Pi-Hole.

Secondly, WireGuard gives you full access to logs since you’re in charge after all. Tailscale does not, and you might need to upgrade to a higher tier to get more info out of them.

In short, to customize for maximum performance and control, choose WireGuard.
For lots of built-in features and large networks, choose Tailscale.

Performance

Using a VPN will inherently slow your connection down because it has to 1) pass through the VPN server and 2) encrypt the traffic. Therefore, when comparing VPN servers in terms of performance, you want low lag and fast data transfers.

WireGuard is more performant than both OpenVPN and Tailscale. The WireGuard protocol is directly in the Linux kernel. Its stateless design means it doesn’t have to spend resources to keep track of client sessions. Lastly, WireGuard consumes less battery power on mobile devices.

Tailscale is slower than WireGuard. This makes sense because Tailscale is built on top of WireGuard and adds extra features that require more computing resources. There are other technical reasons, too, like the fact that your traffic is sometimes routed through relays.

WireGuard is faster in absolute terms.
Tailscale is still decently zippy, so its extra features might be worth the tradeoff to you.

Reliability

A VPN server is no good if you can’t connect when you need it, so let’s talk about how these two stack up when it comes to reliability.

For WireGuard, you’ll be responsible for it all. That means:

• You’ll most likely need to set up dynamic DNS.
  If it goes down, you might not be able to find your VPN server on the internet.
• Port forwarding to the Raspberry Pi needs to be set up on your router correctly.
• If there’s a misconfiguration, you might run into a situation where you’ve connected but still can’t access some other machine (like a NAS) on your network.

Tailscale has come up with answers for each of these problems. First, your client device can connect through Tailscale’s website, so you don’t have to worry about maintaining your server’s IP address.

Second, you don’t need to use port forwarding. This is important for those of you with an ISP that puts you behind CGNAT, a situation where port forwarding won’t work. Tailscale gets around this problem with an advanced technique called hole punching.

Lastly, Tailscale provides contingencies for reachability problems, providing global relays and peer relays to make sure that your devices can connect.

Ultimately, WireGuard and Tailscale are equally reliable if you know what you’re doing. But overall, Tailscale can be considered more dependable when it comes to requiring less work to ensure that all devices on the VPN will always be able to communicate.

Which One Should You Use: Tailscale or WireGuard?

To recap, here are the differences between Tailscale and WireGuard on a Raspberry Pi:

	WireGuard	Tailscale
Raspberry Pi Support	• Server works on all models. • Supports all types of clients.	• Server works on newer models only. • Supports all types of clients.
Installation	• Requires port forwarding. • Other networking steps.	• Works without port forwarding. • Easier to install for non-techies.
Privacy	• Traffic private by design.	• Traffic passes through company servers.
Security	• Requires configuration. • Smaller attack surface.	• Preconfigured for security. • Larger target for hackers.
Price	• Completely free.	• Freemium subscription plan.
Features	• Features added manually. • Full control of logs. • More customizable.	• Lots of built-in features. • Limited access to logs. • More scalable.
Performance	• Faster.	• Fast.
Reliability	• Depends on user setup.	• Multiple relays provided.

If you still can’t decide, let me put it into plain language for you.

WireGuard makes the most sense if you want to have full control of your VPN server so that it works exactly the way you need it, especially if you prioritize performance, privacy, and security. Sure, you’ll have to put in more work, but every aspect can be customized.

Tailcale is the more convenient VPN server if you’re willing to hand some of that control over to a company to manage. Maybe you have many users connecting from different locations, who aren’t necessarily tech-savvy, and you need all of it to just work. Or perhaps you need extra features that would be too complex to configure yourself. In that case, Tailscale is the easier solution.

Both are free to install, so nothing is stopping you from giving each one a test spin to decide which one you like best.

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