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An interesting Tailscale + Docker gotcha

2026-01-29T00:00:00Z

As I’ve written about before, I use Tailscale for a lot of things. I thought I had it set up in a reasonably secure manner, but I recently noticed a problem.

I use Tailscale’s ACLs to limit what each node can access, based on the tags I apply to it. So an app node can’t access anything via Tailscale, while an integration or server node can access things tagged with either app or integration. This is expressed pretty simply in the Tailscale ACL JSON:

{
	"tagOwners": {
		// Servers that can be SSH'd into
		"tag:server": [],
		// Applications that are exposed on tailscale but never connect out
		"tag:app": [],
		// Things which talk to other services over tailscale (connecting to apps etc)
		"tag:integration": [],
	},
	"grants": [
		{
			// Users can access everything
			"src": ["autogroup:member"],
			"dst": ["*"],
			"ip":  ["*"],
		},
		{
			// Servers and integrations can access integrations and apps
			"src": ["tag:server", "tag:integration"],
			"dst": ["tag:integration", "tag:app"],
			"ip":  ["*"],
		},
	],
}

Over the past week I’ve been setting up a private Forgejo instance behind Tailscale, complete with an actions runner that runs things using a docker-in-docker container. I didn’t want the runner knowing anything about Tailscale, so I had it configured to speak to Forgejo direct over HTTP (forgejo:3000) instead of using full Tailscale HTTPS URL that I use when accessing it (http://git.example-net.ts.net/)¹.

Everything was going fine, until I forgot to do that translation… and it worked. My Forgejo action runners could access anything on my tailnet. I run several things on Tailscale that just have authentication turned off, on the basis that only authorised devices can access them. Things like the admin interface for this website. I definitely didn’t intend for any workflow I run on my git server to have access to edit my website!

This wasn’t just limited to Forgejo, either. Any docker container I was running could access the tailnet. In hindsight it’s fairly obvious why: the host is running Tailscale, connected as a node tagged with my server tag. That creates a tailscale0 interface, and automagically sets up iptables rules to route Tailscale traffic over the interface. Docker also automagically sets up iptables rules to bridge traffic, and apparently these two sets of rules interact in such a way that traffic from Docker containers is allowed to route via the tailscale0 interface.

I say it’s fairly obvious in hindsight — there’s no reason why Docker would special case any particular host interface after all — but it still feels pretty surprising. Because both bits of software inject their own iptables rules, I never really had a good mental model for how they interact. The host Tailscale node was a completely separate building block to Docker. It would be a pain to use either of them if they didn’t do these rules, but it’s also one of the reasons I don’t really like “magical” things².

There are lots of ways to fix this, but none of them feel particularly great. You can configure both Tailscale and Docker to not automatically fiddle with iptables and handle the rules yourself, but I really hate dealing with iptables³. As a stopgap I did hold my nose and add some iptables rules to drop traffic to the tailscale0 interface if it originated from the IP ranges that Docker was configured to use:

iptables -I DOCKER-USER -s 192.168.0.0/16 -o tailscale0 -j DROP
iptables -I DOCKER-USER -s 172.17.0.0/12 -o tailscale0 -j DROP

The DOCKER-USER chain is a nice little escape hatch; it comes before the main auto-generated DOCKER chain, and Docker leaves the rules in it alone.

So I added these rules, and felt pretty good about myself, and then… everything started breaking in weird ways. After some debugging I realised the problem was DNS⁴. The server’s DNS resolver is 100.100.100.100, a special Tailscale address. This is so that it can resolve tailnet hostnames via MagicDNS (and so I don’t have to configure my custom DNS servers manually on each device; Tailscale does it for me). My new iptables rules inadvertently dropped all the DNS packets coming from docker containers. D’oh.

Obviously the solution here is to double down and add MORE iptables rules:

iptables -I DOCKER-USER -s 192.168.0.0/16 -d 100.100.100.100 -o tailscale0 -j ACCEPT
iptables -I DOCKER-USER -s 172.17.0.0/12 -d 100.100.100.100 -o tailscale0 -j ACCEPT

This got DNS working again, but it all feels a bit gross. Not least because to actually make these persist you need to use iptables-save, and then you also get all the rules that both Docker and Tailscale have inserted. I came across a script to filter out the Docker ones, but… yuck⁵.

I realised a cleaner idea might just be to lock down what server tagged nodes could access within Tailscale itself. That way I can avoid touching iptables at all. It’s handy to be able to curl services from the host when debugging, but it’s not really necessary. So I removed that access, and… stuff broke again. I’m using my Forgejo instance as a registry for some of the docker images I run, so the docker daemon needs to be able to reach it. I ended up making a new tag for infrastructure, which can be accessed from server devices. This does still allow all the docker containers to reach Forgejo, but I already have it set up with appropriate access controls and public/private repository splits. Forgejo is a service designed to run publicly, so this seems a reasonable trade-off for convenience. I used the tests feature of Tailscale’s ACL config to make sure I’d got the rules right:

{
	"tests": [
		{
			// Servers can only access infrastructure
			"src":   "tag:server",
			"proto": "tcp",
			"allow": [
				"tag:infrastructure:8080",
			],
			"deny": [
				"100.84.16.43:8080",
				"me@example.com:8080",
				"tag:server:8080",
				"tag:app:8080",
				"tag:integration:8080",
			],
		},
	],
}

The whole situation still feels a bit messy. If I ever get around to switching to nftables I might loop back and manually craft some rules for routing traffic, instead of leaving Tailscale and Docker to do their own thing.

I discovered later on that logging into the container registry at forgejo:3000 actually issued a redirect to https://git.example-net.ts.net/ so this was all basically for naught… ↩︎
I didn’t use Tailscale’s MagicDNS for a long time just because the word “magic” put me off. Only when I eventually got around to learning how it worked, and seeing that it wasn’t really that magical under the hood, did I change my mind. ↩︎
nftables seems far better in lots of ways, but I can’t really be bothered migrating. Maybe next time I reimage the server for whatever reason… ↩︎
It’s always DNS… ↩︎
Again, nftables would almost certainly help here. It actually has (gasp) configuration files. But again, I really didn’t want to spend the time migrating. ↩︎

Exposing game servers over Tailscale

2025-12-07T00:00:00Z

I’ve recently been playing a lot of Factorio with a friend. I’ve been hosting, but my desktop computer is behind far too many layers of NAT, and I can’t be bothered dealing with setting up port forwards. Up until today we made do with Steam’s networking support, which in our case ended up relaying the connection via one of their servers. This is amazing as a free, no-hassle service, but the performance was so-so. We’d get random lag spikes, or the initial map download would crawl along at about 1/100th of the speed we should be able to get. We’re both fans of Tailscale though, so maybe there’s an easy solution there?

Tailscale even have an article on sharing a Factorio server but it’s a ten minute long video¹, and focused on setting up an actual dedicated server in Docker rather than just clicking the convenient “Host” button in the game client. What we did instead was:

I shared my desktop’s Tailscale node with my friend, by creating a sharing link in the Admin console
My friend accepted the link, and could then see my machine in their admin panel
I used tailscale lock to sign my friend’s desktop’s node key, as I have tailnet lock enabled
I added a grant to my tailnet’s ACL to permit access from my friend to the specific IP/port on my tailnet:

		{
			"src": ["friend@example.com"],
			"dst": ["100.0.0.42", "fd7a::42"],
			"ip":  ["udp:34197"],
		}

After this, my friend could connect to Factorio by entering the Tailscale IP address, or the Tailscale hostname (as they use MagicDNS). Running tailscale status shows that Tailscale managed to establish a direct connection despite the many layers of NAT involved, and the performance improvements were significant and immediate.

We did a bit of testing, and confirmed that no other services on my machine are accessible. And sharing a machine by default only allows it to accept incoming connections, so I can’t get unwanted access to anything on my friend’s Tailnet, either.

I’ve written before about all the different ways I use Tailscale; this is yet another new way it’s solved a problem for me.

I’m not a fan of video tutorials at the best of times, but especially not when I want to do something as quickly as possible so I can get back to ~~my addiction~~ growing the factory. ↩︎

Avoiding the Consequences of Dumb Laws with Tailscale

2025-09-30T00:00:00Z

More and more sites are implementing privacy-invading age checks or just completely blocking the UK thanks to the Online Safety Act.

Protecting kids from some content online is certainly a noble goal, but the asinine guidance from Ofcom, threats of absolutely disproportionate fines, and the stupidly broad categories of content have resulted in companies just giving up or going through a tick-box exercise that offers very little protection but lots of inconvenience and a complete invasion of privacy.

Instead of uploading my ID to some third party company, I’ve taken to proxying my traffic through to a country that doesn’t have such stupid laws. Thankfully, Tailscale makes this really easy. I’ve discussed how I use Tailscale before, but not really covered app connectors. I find Tailscale’s description of these pretty confusing, but they basically amount to automatic, DNS-based subnet routing configurations (or, to put it another way, a per-website exit node). You can safely ignore all references to ‘SaaS apps’ in their docs.

I create a custom app connector, and give it the domains to be included:

App configuration in the Tailscale admin console

Tailscale then magically resolves those domains, and has the ‘connector’ advertise routes for them. Any client that accepts routes will start sending requests to the connector, which passes them onto the Internet at large. Any other traffic is left alone, unlike when you use an exit node.

The special bit here is how you can specify wildcard domains. Tailscale proxies the DNS requests from clients (so it can inject responses for nodes on your tailnet), which means it can dynamically update the routes as you resolve new domains. I tried to set this up more manually, and quickly came unstuck: despite using the same DNS servers, my server and my desktop would get different responses for the same query as it varied by geography. Trying to get the full set of IPs (and keeping them updated) would have been a nightmare. Tailscale expanding the wildcards nicely sidesteps all of that.

At first I was just proxying the traffic to one of my servers, but just today I added a new connector for Imgur and found I was still blocked, just for different reasons. They not only block my entire country but also a load of known datacenter IP ranges. Hmph. I fixed this by hacking up a new side project: tsv. It’s a simple Go app that accepts traffic from the tailnet (advertising itself as both an app connector and an exit node), and passes it on to another VPN.

There are lots of other ways you could accomplish this, but this makes it so all my devices can still access services without any additional configuration. As long as Tailscale is installed, the Internet will still work as it’s meant to, without all the nonsense. If I come across a site that doesn’t work, adding it is trivial: I just make a new app connector in Tailscale.

Obvious disclaimer: the laws in the UK are binding on the service providers, not the end user. Doing this sort of thing in other countries might be illegal. I don’t know; do your own research! Also all of this is a workaround for something that should be fixed at a legislative level, but I’m not holding my breath.

10 Weeks with an Apple Watch 10

2025-09-09T00:00:00Z

My watch. Yes, I am available for wrist modelling opportunities.

Around ten weeks ago¹ I picked up an Apple Watch 10, and have been wearing it almost constantly since. It’s not my first Apple Watch — I had a Series 5 for a bit back in 2020 — but it’s the first time I’ve actually stuck with it. Ten weeks seems like an apt time to reflect on it.

Firstly, why did I even bother? Well, for a couple of years I’d been wearing a Xiaomi Smart Band 7, mainly to monitor my sleep stats and set alarms that won’t wake up everyone else nearby. Its battery life was fantastic — with notifications and other things turned off, I got about a month of use between charges — but actually using it felt like trying to order food via the medium of interpretive dance.

My biggest gripe was the screen lock. If I didn’t have the screen locked then I’d periodically trigger it during the night when I moved around and it came in contact with my chest or leg. With the lock enabled you had to deliberately swipe up from bottom to top to enable interaction, but it didn’t work reliably. When I wanted to adjust an alarm, I’d be stood swiping repeatedly trying to get it to respond. When you finally get it unlocked, the whole interface is just fiddly.

The other issue was the data quality. There were some nights when I’d been woken up, sometimes even getting up and moving around, and it just didn’t show it in the data. If it can’t even get whether I’m asleep right, can I trust anything else it says?

I spent a while researching the best devices for sleep tracking. The Oura ring came highly recommended, but it was expensive and required a subscription to do anything useful. No thanks! The Apple Watch was consistently rated pretty well, and I reasoned I could pick up a refurbished older unit. I’ve been using an iPhone as my daily driver for a while, so it’d fit right into my begrudged walled garden.

The Series 10 has a significant advantage, though: it charges much quicker than all the previous generations. On a 30-minute charge, the Series 10 can go from 0 to 60%; the 9 can only make it to 40%, and my old 5 a measly 30%. Shorter charge times means I’m far less likely to leave it on charge and wander off without it. In some ways the daily charging is more convenient than monthly: the wireless charger sits on my desk, and I plop the watch on it for a little while in the evening; I don’t need to dig out the weird pogo-pin connector that has vanished sometime in the last four weeks, then carefully arrange it so it stays attached.

How a watch maybe saved my life

One of the big features of the Apple Watch, like many other wearable devices, is health and fitness tracking. I didn’t think much about this, beyond the sleep data I wanted, at first. I’ve never had a particularly good relationship with exercise², but I do like some good statistics. I started going for walks more often to get more data and see the graphs of VO2 max and HR recovery gradually inch up. That wasn’t the most profound effect on my health, though…

The recent versions of the Apple Watch have a feature that monitors for sleep apnea, a disorder where you don’t breathe properly during your sleep. I knew I wasn’t sleeping great — that’s why I was paying attention to sleep tracking data — but was still a bit surprised to get a notification from Apple Health after wearing the watch for 30 days. It gives you a graph to print and take to your doctor. So I diligently booked an appointment and a few weeks later went to see my GP.

The appointment went about as you’d expect: talking about referral to a sleep centre for a study, and so on. Towards the end, the doctor took my blood pressure (sleep apnea can be caused by, and can cause high blood pressure, in a lovely little vicious cycle). I don’t think either of us expected anything; it was just one of those standard checks for a related problem. After taking the reading, the doctor looked at me and said, “I can’t let you leave with a BP like this”. Yikes!

Blood pressure readings are split into stages: normal is under 120 mmHg³ over 80 mmHg⁴, stage 1 is up to 140/90, stage 2 is up to 180/120, and above is simply called “crisis”. Guess where I was? Also, fun fact: depending on how exactly you count and attribute things, hypertension comes out as the single largest cause of death in humans. It doesn’t kill you outright, but contributes to strokes, coronary artery disease, heart failure, and lots of other lovely things you don’t want on your CV.

After doing a few more readings, it settled down to just under the “crisis” stage and into the “holy crap, start treatment immediately” stage instead. I won’t labour on much more about this, but things are definitely moving in the right direction now⁵.

While the Apple Watch didn’t literally save my life, it triggered the chain of events that led to this diagnosis and treatment. Who knows what would have happened had it remained undetected? Probably nothing good. Also, go check your blood pressure! It’s simple to do and simple to treat if there is an issue, but so many people are walking around with hypertension and not even realising.

Building gates in the walled garden

Even though the watch is arguably a life-saver, not everything is rosy. It’s an Apple product, so you’re firmly locked in a walled garden, jealously guarded by people wearing black turtlenecks. Fortunately, there are a few ways to make it less painful.

All the health and fitness data is stored in Apple Health. You can export data as a big messy file, but it’s a very manual process to do so and the data format is gnarly. Luckily, there’s an app for that! Health Auto Export can, well, automatically export health data. It does what it says on the tin. It can send the data to Home Assistant, over MQTT, or dump it in some cloud file services, but I just have it post it all to a REST endpoint on a service I wrote. Then I dump it all in a database and can do whatever I want with it!⁶

Another tool that’s more useful on the watch itself is Apple Shortcuts. This is their no-code “if-this-then-that”-type thing. You can make automations or shortcuts that run a number of tasks. I have a whole slew of them I access via a complication⁷ on my watch face: one which prompts for input and adds an item to my to-do list (swiping to write letters is surprisingly not horrible), one which lets me select from a bunch of pre-written ones (“charge kindle”, “take laundry out in 1 hour”, type things), one to log my weight into Apple Health, one which can open and close the blinds in my room, and so on. It’s a surprisingly robust and easy-to-use system and offers just enough freedom that I’m not constantly grating on the edge of the walled garden.

Shortcuts being able to initiate arbitrary web requests is the real killer feature for me. Anything I can’t do on the watch itself, I can just farm off to a web server and connect it up with a shortcut. No need to learn Swift or pay Apple for the privilege of being a developer! For a lot of things, like controlling the blinds or adding to-do items, I already had a HTTP endpoint available and exposed over Tailscale⁸. Adding it to the watch was just a case of entering the right things in the Shortcuts app.

Daily nitty-gritty

There are lots of other little bits and pieces that come up when using the watch daily. I don’t think I can bundle them up into a pleasing narrative arc, so instead please enjoy some disjointed paragraphs of observations.

The Apple Watch has a lot of nagging abilities. It can notify you about your fitness “rings”, prompt you to stand up every hour, count how many seconds you wash your hands for, etc. I think I’d dislike these just on general principle, but the way it does them is so condescending it’s painful. I think there’s probably a cultural divide issue here, but there is no way in British English to say “Great job! You washed your hands for 30 seconds!” without it sounding like you’re being amazingly sarcastic or like you’re talking to a young child. So I turned all of that nonsense off. It’s meant to be a tool not a wannabe life coach.

You can access Maps directly on the watch and even do navigation. It works really well. The navigation mode has some nice haptic feedback: it does a short pulse as you’re approaching a turn, and then a long pulse at the actual turn. I like it a lot more than having to dig out my phone or have the directions read out. You get one pulse, glance down and see where you need to go, then it reminds you a little later when it’s time to do it. It’s a delightful user experience.

Watchfaces aren’t quite so delightful. There’s a limited number of built-in ones, and some are “exclusive” to the Ultra Series, and you can’t use them on a peasant watch like a Series 10. Annoyingly, there’s not one that does exactly what I want: a plain analogue clock with an inset date and four complication slots around the outside. Instead, I have to use one of the slots to show the date. There are third-party watchfaces, but they have issues. Firstly, there’s no actual API for making watchfaces⁹, so what they do is bodge it horribly by using a photo background that has fake widgets on it. On top of that they’re almost universally subscription-based. Again, no thanks¹⁰.

The issue I had with the Smart Band triggering when I was sleeping is solved trivially on an Apple Watch, by virtue of it having a physical button in the crown. When you put it in sleep mode, you have to double-press the crown to unlock it before it’ll do anything else. It hasn’t misfired once while I’ve been using it.

Sleep data; spot when I swapped devices!

Finally, a special mention for the gesture controls. If you raise the watch it reliably wakes up (switching from a low refresh rate, dimmed screen to an active, brighter one); you can then double-tap your index finger and thumb together and it will scroll down or page through whatever you’re looking at. The killer feature for this is navigating recipes: you can advance to the next step in a recipe while your hands are covered in flour. It’s also handy for reading notifications: when one pops up, you can double-tap to expand it, then, when it gets to the bottom, it’ll outline the default button (often “Dismiss”) and you can double-tap again to click it.

The verdict

I normally don’t like writing an actual labelled conclusion, but it feels like one is needed here! Overall, I’m happy with the watch. The daily charging doesn’t bother me, the data gathered seems reliable, the health monitoring has obviously paid dividends already, and the walled garden isn’t too chafing. It’s a straight upgrade over my old Smart Band, and I think it was worth the cost.

The original reason for getting the watch was better sleep tracking, though, so how well did it do? I’m much happier with the data: it seems to more accurately represent when I was awake in the night, and overall the sleep phases just seem to make more sense. You can see in the graph that the old data switched frequently between phases, and they didn’t quite line up for some reason; towards the right when the Apple Watch is supplying the data instead there’s a much more consistent pattern of sleep phases that repeat over the course of the night.

I’m not going to advocate that you go out and buy one, though. I know my requirements and usage aren’t typical, and I’ve also not got experience with any recent Android Wear alternatives or the new version of the Pebble watch that’s coming soon. You should definitely get your blood pressure checked, though!

OK, it’s more like 14 now, it’s taken a while for this post to make its way from my brain into text. ↩︎
Exercise for the sake of exercising just seems so overwhelmingly tedious and boring to me. And other types of exercise generally require social interaction, coordinating with people, and so on. ↩︎
Who decided to use “millimetres of mercury displaced” as a unit? You can’t just put random chemical symbols in units! That’s not how this works! ↩︎
Blood pressure readings have two parts: systolic (the pressure when the heart is beating) and diastolic (the pressure between those beats). They’re generally presented with the systolic reading on top and the diastolic reading below, and read as “X over Y”. Now you know what some of the random numbers they shout in medical shows mean! Yay learning! ↩︎
No thanks to how much salt is in everything. I’m pretty sure I’ve had at least twice the recommended daily amount of salt in a single serving before. Don’t even get me started on the things that are “low salt” but are still full of sodium from other sources. I don’t have a problem with ionic compounds, I have a problem with sodium! ↩︎
This mainly looks like drawing graphs that are slightly different to the graphs in the Apple Health graphs, for reasons I’m not sure I can explain. Making graphs is fun, OK? ↩︎
Complications are basically just home screen widgets, but with a fancy name because they’re on a watch. ↩︎
Tailscale actually causes me some problems here: everything works fine when the watch is connected to my phone, as the phone handles the Tailscale part, but if I’m not carrying my phone the watch will try to connect over WiFi directly and doesn’t understand anything about Tailscale. It happens infrequently enough that I’ll just live with it; it’s not much worse than having no signal on a phone. ↩︎
Yay walled gardens… ↩︎
I don’t object to subscribing to things in general, but it has to be something that’s worth the ongoing cost and offers something in return for the subscription. A watchface doesn’t need enough ongoing maintenance to justify subscribing to it, it’s just a cash grab. ↩︎

How I use Tailscale

2025-06-25T00:00:00Z

The Tailscale logo

I’ve been using Tailscale for around four years to connect my disparate devices, servers and apps together. I wanted to talk a bit about how I use it, some cool features you might not know about, and some stumbling blocks I encountered.

I’m not sure Tailscale needs an introduction for the likely audience of this blog, but I’ll give one anyway. Tailscale is basically a WireGuard¹ orchestration service, with lots of nice features sprinkled on top. It’s a subscription product, but it has an insanely generous free tier that covers basically anything you’d ever want to do as an individual. They also open source all their client software, and there’s a third party control server implementation called Headscale if you want to avoid the hosted system entirely.

Basic connectivity

At its core, Tailscale lets you easily connect from one device to another, even if they’re not directly exposed to the Internet. You install the Tailscale client wherever you like (on your phone, computer, servers, Raspberry Pi, etc), authenticate the machine with the control server, and it can then talk to all the other machines on the tailnet using their private Tailscale IP addresses.

That isn’t anything revolutionary: it’s the basic premise behind VPNs. But Tailscale makes it so easy. You don’t have to bother with any networking configuration. You don’t have to distribute keys. You just install the client², and login.

For example, my home automation service runs on a Raspberry Pi that sits behind two different routers. I installed Tailscale on it³, logged in, and immediately I could SSH into it from my computer or my phone even when they’re on different networks.

Speaking of SSH, Tailscale has special support for it whereby it handles any incoming connection to port 22 from the Tailscale network, and deals with authentication itself. No public keys or passwords: if you’re logged into Tailscale you can be logged into the machine. This is particularly handy when you SSH from a phone, as proper credential management is a bit of a nightmare there.

Exposing entire machines is just the start, though. If you run multiple services on the machine you need to remember which port they’re all on. Yuck. Instead, you can expose individual services as their own node on a tailnet. There are lots of options for doing so: there’s an official Docker image, a Go library, and many third-party tools (such as my own Centauri and tsp).

Not just a VPN

Exposing individual services wouldn’t be much use if you still had to remember their IP addresses. For a long time I manually added DNS entries for Tailscale nodes, allowing me to connect to http://grafana/ instead of http://100.73.190.100. Recently I switched to Tailscale’s MagicDNS, though, which takes care of that for you. Every machine on the tailnet gets an automatic DNS entry based on its name.

I initially shied off of this because it changes the DNS resolver on every machine it’s installed on, and it all seemed a bit too “magic” for me⁴. I got fed up with manually adding DNS entries though, so I spent a bit of time learning about it and got over my knee-jerk “what on earth is going on?!” reaction. The DNS controls also let you force a specific upstream DNS server. I use NextDNS everywhere, so having Tailscale automatically configure this for me on all my devices was a bonus⁵.

As well as the short names, you can resolve nodes on the tailnet using a slightly longer form: machine.your-tailnet.ts.net. The “your-tailnet” bit is randomly generated, and you can reroll it in the control panel to find a fun one. But why waste time say lot word, when few word do trick? Because Tailscale can make these addresses globally routable, and issue TLS certs for them too.

Say you’re developing something on your local machine, and want to get feedback from someone. You can use Tailscale’s “funnel” feature to expose it publicly:

tailscale funnel 127.0.0.1:8080

With no other options, this will expose the service over HTTPS on port 443. You can then invite people to visit https://machine.your-tailnet.ts.net and they’ll connect through to port 8080 on your machine. They don’t even need Tailscale installed. I don’t use this terribly often, but it’s a great quality-of-life improvement on the occasions I do want to share something.

Tailscale also has a “serve” command, which does much the same but only exposes it over your tailnet. This is how you’d use the Tailscale Docker image to expose a normal service onto your tailnet, but it’s also useful for similar development scenarios. Occasionally I’ll want to test something on my phone, and rather than make sure it’s connected to the right Wi-Fi network, recompiling the app to not bind to localhost, figuring out my machine’s IP, and so on, and so forth, I just run tailscale serve and access it over Tailscale.

Authentication, two ways

One of my minor frustrations with Tailscale was how cumbersome the authentication process was. I logged in using GitHub, and every time I tried to login to Tailscale, I had to bounce through the GitHub OAuth flow and then select which organisation I wanted to use. Even if I was logged in to GitHub, it still shows the permission page every time. It’s not a dealbreaker, but it’s definitely not smooth. This is what it looks like:

Logging in to Tailscale with a GitHub account

Tailscale have since added the ability to sign in with a custom OIDC provider, so I set up a KeyCloak instance, and my login flow now looks like this:

Logging in to Tailscale with KeyCloak as an OIDC provider

It’s a significantly shorter flow, and because KeyCloak is entirely under my control I can configure how long I stay logged in for. It also reduces my reliance on third parties: if GitHub goes down, or decides to ban my account⁶ or something, I can still access Tailscale.

That’s how you log in to Tailscale, but Tailscale can also assist with logging in to other services. If you connect to a HTTP service over Tailscale, it will add in the following headers:

Tailscale-User-Login: alice@example.com
Tailscale-User-Name: Alice Smith
Tailscale-User-Profile-Pic: https://example.com/photo.jpg

A lot of software has support for accepting login credentials provided by a reverse proxy, which is basically what’s happening here. For example, I run a Grafana instance that’s only exposed over Tailscale. Its config (set in environment variables) is:

GF_USERS_AUTO_ASSIGN_ORG: "true"
GF_USERS_AUTO_ASSIGN_ORG_ROLE: "Admin"
GF_AUTH_PROXY_ENABLED: "true"
GF_AUTH_PROXY_HEADER_NAME: "Tailscale-User-Login"
GF_AUTH_PROXY_HEADER_PROPERTY: "email"
GF_AUTH_PROXY_AUTO_SIGN_UP: "true"

So anyone who presents a Tailscale-User-Login header gets an admin account created with that as their e-mail address. It’s super convenient, but obviously make sure it’s only exposed via Tailscale if you do that!

Other services I run that support this include Miniflux (an RSS reader), Jelu (a book tracker), Linkding (a bookmark manager), and Seafile (a file storage system). If you’re hosting something yourself, look out for “proxy auth” or “remote users” in the documentation or configuration. It’s amazingly convenient to be able to access things without entering credentials.

ACLs, tags and mistakes

For a long time I didn’t bother with any kind of ACLs within my Tailscale network. Every machine could access every other machine. Then one day a thought hit me. The default Tailscale SSH config re-prompts you for user authentication, but I’d disabled that by tweaking the config… That means anyone with access to any of my machines (or who managed to get Tailscale credentials out of one of my apps) would be able to SSH into anywhere else on my network. Even as root! Compromising a small bit of my network would immediately lead to a complete take-over. What’s the point in defence-in-depth if you roll out a red carpet over the drawbridge for any attackers?

The first and most obvious fix for this was to restrict root access over SSH. I changed my Tailscale ACL to prompt for reauthentication for root access, but still allow regular SSH unprompted:

{
  "ssh": [
    {
      "action": "accept",
      "src":    ["autogroup:member"],
      "dst":    ["autogroup:self"],
      "users":  ["autogroup:nonroot"],
    },
    {
      "action": "check",
      "src":    ["autogroup:member"],
      "dst":    ["autogroup:self"],
      "users":  ["root"],
    },
  ],
}

This still didn’t sit right with me, though. Why should a random webserver be able to (theoretically) SSH into my desktop computer unchallenged? Tailscale allows you to do more advanced ACLs by applying tags to devices. I dutifully created a bunch of tags, and went through and tagged every device: user, server, app, container, and so on. This, it turns out, was a mistake. I could no longer SSH to anywhere. If I’d read the docs properly, I might have noticed how they describe tags:

Tailscale tags are how you authenticate and identify non-user devices, such as servers and ephemeral nodes. They serve two primary purposes: to provide an identity to non-user devices and to let you manage access control policies based on purpose.

By applying a nice user tag to all of my devices (computer, phone, tablet and so on), I’d effectively removed my own identity from them. They no longer counted for the autogroup:member source in the SSH config. Whoops. And it’s not easy to fix either:

You cannot remove all tags from a device. A device with a tag-based identity must have at least one tag.

So I’d have to remove all the affected devices, then re-add them. At the time I wanted to roll back all the tags, which would mean reconnecting dozens of nodes to the Tailnet. I did end up doing that, but I also took it as an opportunity to switch to KeyCloak as I mentioned earlier. Setting everything up again was a bit less painful when it wasn’t just correcting a dumb mistake.

I now have a much more sensible tag setup: servers are tagged server, apps are tagged app, and a few special apps are tagged integration. I then use Tailscale’s grants to limit access within the tailnet:

{
  "grants": [
    {
      // Users can access everything
      "src": ["autogroup:member"],
      "dst": ["*"],
      "ip":  ["*"],
    },
    {
      // Servers and integrations can access integrations and apps
      "src": ["tag:server", "tag:integration"],
      "dst": ["tag:integration", "tag:app"],
      "ip":  ["*"],
    },
  ],
}

This stops anyone but a user device from accessing servers, and stops plain apps from accessing anything at all. So for example my Grafana instance is tagged as an app; it doesn’t connect out over Tailscale for anything, it only exposes its interface over Tailscale. My home automation software is tagged as an integration, as it reaches out to other services over Tailscale (e.g., to push metrics it receives from devices).

You could go even further and limit which specific machines talk to which others, but I think this tier system sets reasonable boundaries for my use without getting too much in the way.

Even more

There are lots of other cool features offered by Tailscale that I’ve not covered: exit nodes (allowing you to route normal Internet traffic over Tailscale; very handy when you’re behind a router you don’t trust, or if you want to appear as being in another country for totally legitimate reasons); Tailscale lock (a system where existing nodes have to verify any new ones, guarding against both unauthorised access and Tailscale themselves inserting nodes into your network); file sharing, and more I’ve probably forgotten.

As I mentioned before, an awful lot is available on the free personal plan. It’s definitely worth checking out if you manage servers, or self-host anything. I can’t imagine going back to managing servers and private apps without Tailscale, and I’m excited to see what else they do going forward.

If you’re not familiar with it, WireGuard is a modern VPN included in the Linux kernel. It’s basically the only VPN that isn’t terrible. ↩︎
They have installation instructions and packaged versions of the client for just about every device you can imagine: Windows, Mac, every major Linux distribution, iOS, Android, etc, etc ↩︎
They even have an apt repository specifically for raspbian builds, so it’s super easy. ↩︎
Lots of people seem to treat “magic” as a good thing in software. I think it’s the absolutely opposite. I want to know how something works, not for it to be inscrutable! ↩︎
This is entirely optional, of course, you can just let each device do their own thing as well. ↩︎
I don’t think this is likely, but it’s one of my biggest concerns about using “social” logins. More-or-less all of these services can arbitrarily ban you with no recourse; why would you trust them as keyholders to other things? ↩︎