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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. ↩︎

Why you should be using HTTPS

2016-06-17T00:00:00Z

The EFF’s HTTPS Everywhere logo

One of my favourite hobbyhorses recently has been the use of HTTPS, or lack thereof. HTTPS is the thing that makes the little padlock appear in your browser, and has existed for over 20 years. In the past, that little padlock was the exclusive preserve of banks and other ‘high security’ establishments; over time its use has gradually expanded to most (but not all) websites that handle user information, and the time is now right for it to become ubiquitous.

Why use HTTPS?

There are numerous advantages to using HTTPS, both for the users of a website and for the operator:

Privacy

The most obvious advantage is that HTTPS gives your users additional privacy. An insecure (HTTP) request can potentially be read by anyone on the same network, or the network operators, or anyone who happens to operate a network along the path between the user and the server.

Users on shared WiFi networks (such as those in coffee shops, hotels, or offices) are particularly vulnerable to passive sniffing by anyone else on that network. If the network is open (as is frequently the case) then anyone in radio range can see exactly what the user is up to.

Integrity

HTTPS also helps to maintain the integrity of your site. With a plain HTTP request, there’s nothing to stop anyone in between the server and the user from modifying the content of the request or the response. This is a frequent tactic used by annoying WiFi gateways (such as the ones you’d find in a hotel), dubious ISPs who want to serve you extra adverts, or just plain old nefarious attackers.

If you’re trying to convey some kind of information to users (and if you aren’t, why exactly are you running a website again?) it seems beneficial to both you and them if the information arrives as you intended, rather than in a modified form due to someone or something tampering with it.

Security

If your website has any kind of authentication, or session identifiers, it becomes extremely vulnerable to an attacker monitoring the traffic and stealing the credentials. This was starkly demonstrated in 2010 when Firesheep was released. This tool allowed anyone to quickly and automatically hijack social media accounts of anyone on the same network who was using HTTP to access them.

Even if your login pages are served over HTTPS, if you send a single session ID cookie over HTTP (such as a page you decided wasn’t particularly ‘important’) then an attacker can probably spoof the user’s session and gain full access to their account. Again, in the case of open WiFi networks that could be anyone in radio range.

Search engine rankings

Some search engines use HTTPS as a signal in their ranking algorithms. Google announced in 2004 that it was using the presence of HTTPS as a small positive signal, but that it may strengthen that signal over time as more and more websites switch to using a secure transport. It’s not unthinkable that at some point in the future there will be HTTPS-only search engines.

But… But… But…

There are lots of excuses for not implementing HTTPS. Most of them are either misguided or outdated.

It’s too expensive and/or complicated

In the past, getting HTTPS certificates was a pain. A number of free suppliers have existed for a while but the process for getting their certificates wasn’t particularly straight forward, and many imposed arbitrary restrictions on the certificate parameters. Even once you had the certificate, you had to fiddle about with your HTTP server configuration to make it work, remember to manually get a new certificate when the old one expired, and lots of other annoying busywork.

With the arrival of Let’s Encrypt, all that changed. You can retrieve and deploy a free HTTPS certificate with two or three commands. Renewal can be handled completely automatically with a single command executed by cron.

There’s no point; nothing on my site is sensitive

You might not think your content warrants privacy, but can you speak for everyone who accesses it? Even content that seems mundane to you — such as travel advice, or technical writing — could be used to build up a profile of a user. If an attacker is monitoring traffic in a coffee shop and sees a user looking at travel advice and weather forecasts for a foreign country, he could use that information to plan a burglary knowing that the user will be away. Similarly, some content which is perfectly mundane to you may actually be very sensitive in other countries with repressive governments. HTTPS makes it much harder for these people to snoop on traffic.

From another angle, if you’re offering any kind of information, instructions, or especially file downloads, there’s a severe risk to users if the content is modified on its way to them. An evil sysadmin could rewrite your travel advice to suggest visiting the local drug dealer’s hangout, or replace your download with a malware-infested version.

HTTPS is slower, uses more resources, etc

Back in 1995 this might have been a valid argument. Enabling HTTPS on a modern server will make an almost negligible difference to performance. If you also enable HTTP/2 (which most implementations only support over HTTPS), it’s likely to actually use fewer resources, and result in a faster, smoother experience for your users. HTTP/2 was designed to work with HTTPS, and designed with modern requirements and networking techniques in mind.

CloudFlare have an excellent demonstration of the benefits of HTTP/2, and it can show speed improvements of 2-3x in a typical environment. On top of being faster, HTTP/2 uses fewer connections which results in less resource overhead on both the server and the client.

So what are you waiting for?

If you run a website and aren’t using HTTPS, give it a try.