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Monthly Meanderings: March 2026

2026-04-01T00:00:00Z

Since last month’s update I’ve been unpleasantly reminded that I’m middle aged, through the medium of a dodgy knee. There’s nothing quite like not being able to stand up without groaning to underscore that you’re not young any more. The ongoing game of “will this seemingly mundane activity make my knee go funny again?” is a delight to play, too. I’m great at it.

Website updates

Two new blog posts this month: the longest way to represent a date is a short thought experiment on absurd date formats, and modern CSS is fun goes through some neat new CSS features I’ve used recently for this site.

I did some design tweaks this month: headers now have a blue background behind them¹, and a lot of components have been redesigned to have a consistent style. You can see that component in action in the new “now playing” widget I’ve added:

VersaEmerge — Redesign Me Fixed at Zero Scrobbled 1h 11m ago

Instead of each component defining its own styles (which were mostly copied and pasted), there’s now a single class that handles the drop shadow, border, background colour, and the optional title. It also applies a consistent format to elements that are clickable: they use the blue accent colour for their borders, and have a glow effect shown on hover.

The now playing widget is part of a larger bit of work I did on importing some music stats. I’m pulling in the data from my Navidrome instance. A new music page shows my most listened albums and artists. Navidrome doesn’t store a complete play history, just the last play and the count, so I can’t do “what I listened to last month” stats until next month.

Other projects

Other than a minor bug-fix update to contempt, my Dockerfile templating/updating tool, I’ve not done much on my other open source projects. I’ve got a bit more work to do finish migrating all my repositories from GitHub to my private Forgejo instance. I’ve also been thinking about mirroring my public repositories to Codeberg so there’s a non-GitHub way to access them.

Entertainment

I apparently only watched a single film in March:

The Substance

2026-03-18

I really didn’t get on with this. It’s too long for what it is, and over-the-top in a way that just didn’t work for me.

Demi Moore and Margaret Qualley were great, but nothing else really was. The cinematography and sound design were too affected, the plot was pretty shallow and obvious, most of the body horror fell into the uncanny CGI valley for me.

It’s not completely without merit: there were around 40 minutes in the middle where I was really into it, but that’s not really enough given it’s closing in on a 2.5 hour runtime.

There’s something to be said for the message it’s presenting about women in Hollywood, too, but it was very heavy handed. Dennis Quaid’s character is even called Harvey; it’s not so much a subtle nod as a sledgehammer to the face.

Instead of films, I’ve been watching a bunch of TV. After devouring The Pitt last month, I struggled to find something to fill the hole it left. I settled on catching up on Chicago Fire and Chicago P.D.. They’re both mostly about getting things done without personal drama becoming the primary focus. They’re not quite as grounded as The Pitt, but at least they’ve not completely gone off the deep end like 9-1-1 where the first responders end up in space somehow?

I’ve also watched the first two episodes of SNL UK. I didn’t have very high expectations, and it gave me a pleasant surprise. Both episodes so far have some hilarious sketches, and are obviously written by British comics with the typical darker, more sardonic humour that separates us from the USA.

Last but not least, board games! I spent a weekend at a tabletop/LAN event with friends, so got to physically play some games for a change. I also kept up with some turn-based games on Board Game Arena, as usual.

6 plays
4 plays
4 plays
4 plays
3 plays
3 plays
3 plays
2 plays
2 plays
2 plays
2 plays
2 plays
1 play

Around the web

Warranty Void if Regenerated

Some really cool speculative fiction about a future where all software is written by LLMs, and the social effects that may have. Unfortunately the story itself is written with an LLM, and that becomes painfully obvious about a third of the way in. By that point I was already hooked, though.

My 2-step process for AI-free blogging

Speaking of LLM-generated text, this short piece by Manuel Moreale made me laugh. I’m by no means anti-LLM, but I really hate people publishing the output like it’s their own work. It breaks the social assumption that the writer put more effort in than the reader, and makes me wonder how much is hallucinated.

25 Years of Eggs

An interesting applied use of coding agents. I’m a sucker for personal statistics. I have no explicit desire to keep my receipts, or generate graphs of my egg consumption, but seeing the graphs makes me question that. The journey to get there is a great read, too.

I made a one-page notebook

The clever paper folding is interesting, but I really like some of the small touches on the page. There’s a nice little “in reply to” callout providing context at the top of the page, you can click to rotate the image further down, and there’s a details element containing a textual version of it. It has that great ‘small web’ vibe of someone who really cares about what they’re doing.

Workers who love ‘synergizing paradigms’ might be bad at their jobs

I haven’t read the full paper, but the summary given by the article is equal parts interesting and amusing. They developed a “Corporate Bullshit Receptivity Scale”, what more is there to say?

It’s meant to resemble painter’s tape, but I’m not sure quite how well it works. ↩︎

Modern CSS is fun

2026-03-17T00:00:00Z

I’ve been doing a bunch of CSS tweaking recently, and keep being surprised by how nice modern CSS is to work with. As someone grey-haired enough to remember writing HTML without CSS, it’s amazing to think how far along web technology has come¹. I wanted to demonstrate some of the handy bits and pieces I’ve used recently.

:has

The :has selector allows you to effectively query for child elements. While a span will match a <span> within an <a>, a:has(span) will match an <a> that contains a <span>. This really shines when combined with more complex selectors, for example:

input {
    border-radius: var(--border-radius);

    &:has(+ .results:not(:empty)) {
        border-bottom-left-radius: 0;
        border-bottom-right-radius: 0;
    }
}

This is part of the styling for my film search box. When the search box is presented initially it has fully rounded corners. But when it is followed by a non-empty results element, it removes the rounding on the bottom corners so that the border continues in a straight line down into the results. You can see it in action below; just enter a few characters (like “the”) to get some results:

You could achieve the same effect by having JavaScript add a class to the <input> element, but I’ll take a CSS solution over a JavaScript solution any day.

Nested rules

You probably spotted this in the example above. It’s what finally made me switch from SCSS to plain CSS. If you have a rule for .foo and a rule for .foo .bar you can just nest them. Not only does it save repeating yourself an awful lot, it keeps everything organised nicely. For example, the CSS for my film list embeds looks like this:

a.film-list {
    display: grid;
    grid-template-areas: "header images" "description images" "meta images";
    grid-template-columns: 1fr auto;
    grid-template-rows: auto 1fr auto;
    row-gap: var(--small-space);

    @media (width <= 800px) {
        grid-template-areas: "header" "description" "images" "meta";
        grid-template-columns: 1fr;
        grid-template-rows: auto auto auto auto;
    }

    & + & {
        margin-top: var(--medium-space);
    }

    h3 {
        font-size: var(--font-size-xxlarge);
    }

    .description {
        /* ... */
    }
}

Everything is wrapped up in a single bundle, including the @media rules for changing the layout on smaller screens, the lovely little & + & rule that adds some extra margin if there are two lists in a row, etc. The & syntax refers to the parent selector, so & + & in this case is the same as a.film-list + a.film-list: it’s very handy! The best part about this is that it’s the exact same syntax as SCSS, so converting is easy². The styled element looks like this:

Watched films ranked

Every film I’ve watched since I started logging, ranked.

Obviously super subjective, and subject to change often and arbitrarily.

264 films

Media range syntax

Once again, you might have spotted this in the previous snippet. I’m not deliberately teasing things, I promise! Back in the day, you did media queries like so:

@media (min-width: 1000px) and (max-width: 2000px) {
    /* some rules that work for screens at least 1000px wide and at most 2000px wide */
}

I always hated this syntax. I always got muddled up as to whether I wanted “min” or “max”, and whether they were inclusive or not. It’s easy to reason through, but it never came naturally. Fortunately you can now just use ranges:

@media (1000px <= width <= 2000px) {
    /* some rules that work for screens at least 1000px wide and at most 2000px wide */
}

I find this style so much easier to write and understand.

Anchor positioning

Trying to dynamically position one element next to another used to exclusively fall within the purview of JavaScript. Fortunately anchor positioning fixes all this. I use this in the film search field I showed above:

.film-search {
    input {
        anchor-name: --film-search-box;
    }
    .results {
        position: absolute;
        position-anchor: --film-search-box;
        position-area: bottom center;
        position-visibility: always;
        width: anchor-size();
    }
}

This does lots of fun things. The .results element is anchored to the input field (via the --film-search-box name), and it’s positioned on the bottom, directly under the anchor. The position-area rule describes a 3x3 grid, with the anchor at the center, so top left would put it diagonally adjacent to the anchor. Next, position-visibility keeps the .results element visible when the anchor isn’t; otherwise when you scroll the anchor off the screen the results would immediately vanish. Finally, the special anchor-size() function makes the .results element take up the same exact width as the anchor.

All-in-all, this puts the results exactly where I want them, without having to deal with any JavaScript at all. I can see how it’d also be amazingly useful trying to do tooltips or other forms of ‘floating’ content too. You can even leave the positioning up to the browser, giving it hints about which order to try, or what property to optimise for (e.g. you can say “anchor to the left or right, whichever has more horizontal space”).

attr() function

This one blew my mind a little. In some of the elements on the site, I’ve added a little label to the top. It looks something like this:

It’s meant to just be a visual flourish, not a semantic title or anything, so I initially just added a ::before selector to each element, customising the content to have the right value. I didn’t like the duplication, though. Now, instead, I do this:

&::before {
    content: attr(data-title);
}

Each component defines its title in a data attribute: <div class="raised-box" data-title="an example">, and the attr function plucks it out and puts it in the content rule. It’s worth noting that this is only widely supported for the content rule, you can’t yet use it for colours or dimensions or other things. It still feels a bit magical, though. Like you’re making a reusable, customisable component with just HTML and CSS.

layers

I’d come across layers a few times, but I never found a need for them. It seemed like something you’d only really need with complicated design systems, or something. Then I had a problem and layers were the perfect solution!

The headings on this site have a whole bunch of CSS attached to them. Currently they look a bit like blue painter’s tape with handwriting on them. This style is applied to all headers, and then the various places that don’t want it had to manually reset everything. I got fed up with that, so decided to add a plain-header class which would “disable” the extra styling:

h2,
h3,
h4,
h5,
h6 {
    /* common styles for all headers, regardless */
    font-family: "Chris Hand", sans-serif;
    font-size: var(--font-size-xxlarge);
    color: var(--text-highlight-colour);
    margin: var(--medium-space) 0;
    line-height: 1;

    &:not(.plain-header) {
        /* do fancy stuff if it _doesn't_ have the .plain-header class */
        transform: rotate(-0.15deg);
        padding: var(--smedium-space);
        font-weight: 800;
        filter: drop-shadow(3px 3px 5px rgb(0, 0, 0));

        a {
            background: none;
            text-decoration-skip-ink: auto;
        }
    }
}

This might seem a bit backwards but I want the default to be styled, as those are far more common. I added this change, sprinkled around some “plain-header” classes, tidied up a lot of duplicate CSS, and things mostly worked. Mostly. Some things stopped working. In a few places the headers had slight tweaks, and they stopped working entirely.

It turns out in moving the rules from a plain h2 selector to a h2:not(.plain-header), I’d made them more specific. Previously a selector like h2.special would have been more specific, so its properties would override those from the less specific h2 selector. My first reaction was to try and hack around it. Changing all the overrides to body h2.special would make them more specific again, but I didn’t want to have to remember to do that forever more.

Instead, I defined some custom layers, and put the header definitions in one:

@layer reset, links, headings

@layer headings {
    h2,
    h3 {
        /* etc */
    }
}

The first @layer rule defines some layers that will be handled in a specific order: first the “reset” layer, then the “links” layer, then the “headings” layer, and then anything not in a layer after that. Rules in one layer don’t have to worry about beating the specificity of rules in another layer, because they’re handled separately.

Note that I couldn’t just put the headings in a layer and call it a day: their rules have to come after the CSS reset, and after the normal link styles, as headers have a bit of extra styling for nested links. If the CSS reset weren’t in a layer, then the * { margin: 0; padding: 0; } type reset would apply over the rules from the headings layer.

Using layers is definitely a bit fiddly, and is not necessary for a lot of sites, but it’s a much cleaner alternative to ugly specificity hacking.

Things I’m looking forward to

There are a few things that aren’t (widely) available yet, that particularly interest me:

sibling-index() and sibling-count()

These new functions are available in WebKit and Blink based browsers, but not Firefox. They give you the index of the element within its siblings, or the count of siblings. For the film list component above, I currently have this abomination for the overlapping posters:

&:nth-child(1) {
    z-index: 5;
    left: 0;
}
&:nth-child(2) {
    z-index: 4;
    left: calc(133px * var(--overlap) * 1);
}
&:nth-child(3) {
    z-index: 3;
    left: calc(133px * var(--overlap) * 2);
}
&:nth-child(4) {
    z-index: 2;
    left: calc(133px * var(--overlap) * 3);
}
&:nth-child(5) {
    z-index: 1;
    left: calc(133px * var(--overlap) * 4);
}

These could be replaced with something like:

z-index: calc(1 + sibling-count() - sibling-index());
left: calc(133px * var(--overlap) * (sibling-index() - 1));

As an added bonus, it would scale to any number of posters. index being 1-based not 0-based is a bit unfortunate as it makes using it in calculations awkward (see 1 offset in both of those rules!), but it’s leagues better than writing 5 separate rules.

random()

Currently only available in Safari. There are a few places where I’d like to have slight random variations of the style. Things like elements that are rotated slightly for aesthetics; they look a bit silly if they’re all identically positioned. I also randomise the icons and positions of my rating stars to break up the visual monotony. Here are a few examples:

Currently I do the stars by hardcoding a bunch of classes and having the backend randomly apply one when it generates the markup for stars. Being able to do it in CSS would be great, though.

Mixins

This one’s so far off it’s not even listed on caniuse.com yet. Mixins are another handy feature of SCSS, that allow you to define reusable blocks of rules, then import them when needed:

@mixin fancy-background {
    background: /*...*/;
}

.some-element {
    @include fancy-background;
}

#other-element {
    @include fancy-background;
}

This would be particularly useful if you can’t easily control the markup to add classes to everything. For example, my footnotes are rendered by a markdown plugin, and don’t easily have a way to add extra classes to them. To style it the same as another element, I currently duplicate a bunch of rules between them both. Mixins would allow me to define those rules once, and then import them in both places.

Aside from JavaScript, which seems to just endlessly reinvent new frameworks and ways to make the most sprawling dependency tree possible. ↩︎
It also means that if your website’s syntax highlighting library doesn’t seem to understand nested rules, you can just pretend your perfectly valid CSS is actually SCSS and it’ll magically work. Grumble, grumble. ↩︎

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. ↩︎

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.

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? ↩︎