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How I use Tailscale

How I use Tailscale

36 comments

·August 6, 2025

abdusco

I tried using `tailscale funnel` against a dummy server `python -m http.server`, and within 10 seconds the bots started to check for vulnerabilities.

Tailscale warns you about how enabling it will issue an HTTPS certificate which will be in a public ledger. But I wasn't expecting it to be this quick.

    127.0.0.1 - - [10/Aug/2025 00:11:34] "GET /@vite/env HTTP/1.1" 404 -
    127.0.0.1 - - [10/Aug/2025 00:11:34] code 404, message File not found
    127.0.0.1 - - [10/Aug/2025 00:11:34] "GET /actuator/env HTTP/1.1" 404 -
    127.0.0.1 - - [10/Aug/2025 00:11:34] code 404, message File not found
    127.0.0.1 - - [10/Aug/2025 00:11:34] "GET /server HTTP/1.1" 404 -
    127.0.0.1 - - [10/Aug/2025 00:11:35] code 404, message File not found
    127.0.0.1 - - [10/Aug/2025 00:11:35] "GET /.vscode/sftp.json HTTP/1.1" 404 -
    127.0.0.1 - - [10/Aug/2025 00:11:35] code 404, message File not found
    127.0.0.1 - - [10/Aug/2025 00:11:39] "GET /s/7333e2433323e20343e2538313/_/;/META-INF/maven/com.atlassian.jira/jira-webapp-dist/pom.properties HTTP/1.1" 404 -

Jnr

I use Headscale, an open source implementation of Tailscale control server. And it doesn't have funnel functionality implemented out of the box, but I use a custom Traefik proxy manager Web UI in which I can expose ports on different Tailnet nodes.

In order to avoid exposing something unnecessarily in the certificate transparency logs, I use a single wildcard certificate, so all the subdomains are not listed anywhere automatically.

I use the same approach for services hosted in the internal subdomain, because I don't want everyone to know what exactly I'm running in my homelab.

mh-

Yeah, I have mixed feelings about CT (certificate transparency) for this reason. Folks are just consuming the firehose and scanning.

And in this case, if the thing you're funnel'ing is on your residential connection, it basically amounts to you summoning a DDoS.

One (obvious?) tip I'd offer is to put your stuff on high non-standard ports if you can. It'll reduce the amount of connections you get dramatically.

tptacek

When you care about this, if you're managing your own certificates, you can issue wildcard certificates.

mh-

Hmm, yeah, that's a great suggestion, thanks!

modernpacifist

A DoS that will disappear once you close the funnel. Tailscale are proxying the traffic so your public IP isn’t exposed. Your choice of port makes no difference.

gitgud

Wait, so bots watch for new records added to this HTTPS cert public ledger, then immediately start attacking?

To me that sounds like enabling HTTPS is actually a risk here…

yjftsjthsd-h

The server was already exposed. All this does is remove obscurity

dijit

I wish this trend of “security through obscurity” should mean that all info should just be exposed would die, its silly and lacks basis in reality.

Even within infosec, certain types of information disclosure are considered security problems. Leaking signed up user information or even inodes on the drives can lead to PCI-DSS failures.

Why is broadcasting your records treated differently? Because people would find the information eventually if they scanned the whole internet? Even then they might not due to SNI; so this is actually giving critical information necessary for an attack to attackers.

homebrewer

IME, moving ssh off the standard port reduces bot scanning traffic by >99%. Not only it means less noise in the logs (and thus higher SNR), but also lowers the chance you're hit by spray-and-pray in case there's a zero day in sshd (or any other daemon really).

afavour

Which is something that makes a notable difference. It’s telling the bots the OP listed are trying Vite endpoints, they’re targeting folks doing short term local web development. Removing obscurity and indicating relative likelihood of still being online is a big shift.

thrown-0825

I use a similar setup, but for anyone following this guide i would not recommend hosting your custom oidc server behind the same tailnet it authorizes.

Any configuration issues will lock you out entirely and you will need to have tailscale support re-enable an oauth provider and its not reversible.

I use an oauth provider to log in to tailscale and keycloak internally as an oidc provider for service to service auth.

Lammy

> 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.

Tailscale do have a very nice product, but privacy-conscious users should be aware that you must disable Tailscale's real-time remote collection of your behavior on your “private” network. See KB1011: https://tailscale.com/kb/1011/log-mesh-traffic

“Each Tailscale agent in your distributed network streams its logs to a central log server (at log.tailscale.io). This includes real-time events for open and close events for every inter-machine connection (TCP or UDP) on your network.”

It's possible to opt out of this spying on Unix/Windows/Mac clients by starting Tailscale with `--no-logs-no-support` or `TS_NO_LOGS_NO_SUPPORT=true` environment variable (see https://tailscale.com/kb/1011/log-mesh-traffic#opting-out-of...), but it is not currently possible to opt out in the Android/iOS clients: https://github.com/tailscale/tailscale/issues/13174

For an example of how invasive this is for the average user, this person discovered Tailscale trying to collect ~18000 data points per week about their network usage based on the number of blocked DNS requests for `log.tailscale.com`: https://github.com/tailscale/tailscale/issues/15326

Also see their privacy policy: https://tailscale.com/privacy-policy#information-we-collect-...

“When you use the Tailscale Solution, we collect limited metadata regarding your device used to access the Tailscale Solution, such as: the device name; relevant operating system type; host name; IP address; cryptographic public key; user agent (where applicable); language settings; date and time of access to the Tailscale Solution; logs describing connections and containing statistics about data sent to and from other devices (“Inter-Node Traffic Logs”); and version of the Tailscale Solution installed.” (emphasis mine)

Anyway, the reason I quoted that part of your post is because Tailscale are using some Fear, Uncertainty, and Doubt tactics here by naming the privacy-preserving option “no-support”, and if you are a free user then you aren't getting support from them anyway, so there should be no downside to keeping your private network private :)

xyzzy_plugh

That section of the policy simply describes how the system works. It's very valuable information for enterprise customers who are effectively their entire market revenue-wise. Think access logs, intrusion detection, and so on. I do not interpret their policies such that they are processing the information you added emphasis to beyond what is necessary to serve the customer. What evidence do you have to the contrary?

The irony of your post, which brings up Fear Uncertainty and Doubt, is certainly not lost on me. I'm also sure you could just ask apenwarr directly for clarification.

benreesman

Eh, as a network administrator you want the netlogs on by default and you very clearly onboard everyone to the network with a memorable warning to do their personal browsing over some other interface. You've usually got at least some minimal audit requirement on any network with high value stuff on it.

It's probably not great that someone trying to use the free sample product lands in the same netlogging regime as the work network default, but I suspect thats more about allocation of attention and priority which understandably goes to the companies that make up approximately all of their business. Keeping the free sample product around after its long bern clear "this is for work computers" is just one of those things. The "no support" suffix on a setting is not to me the smoking gun you make it out to be, and I'm pretty hardcore in my attitudes about surveilance.

I agree it's the wrong default for a purely personal user, but TailScale has enough "good faith actor" points with me that I'll give them the benefit of the doubt on malicious/evil dragnet surveilance ambitions. What could they possibly want with the data of a group of people who are by construction not spending money on a VPN? They'd be storing it at a loss.

mcsniff

This comment should really be much higher.

redat00

Neat way to use Tailscale !

I have a similar set-up, without authentication however, relying on Nebula! https://github.com/slackhq/nebula

sixothree

I love me some tailscale. But it kills the battery on my phone and it kills resolve.conf every time I boot wsl. I wish I had better luck.

em-bee

i use zerotier without problems on the phone. yes, they are no longer open source, but source is accessible and it's not worth the effort to switch.

th0ma5

Straight WireGuard to a single point is completely not noticeable.

mlhpdx

I’ve been experimenting with different ways of using WireGuard but hadn’t heard of the header based authentication Tailscale does. Interesting stuff.

8n4vidtmkvmk

Sounds a bit like a fancier ngrok.

Accidentally wiring everything to everything else sounds kind of scary.

There's 1 or 2 things I wouldn't mind securely exposing to the internet (like Plex) but nothing I need so desperately while I'm out and about that I'd even want to take that risk.

Sounds like this is just for self-hosting?

em-bee

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.

this has me worried. i would not want that. i use zerotier, not tailscale, but the principle is the same. i have my laptops and my phone connected to my servers. given that all of those machines are already on the internet, connecting them into a virtual network does not add any risk in my opinion. (at least as long as you don't use features like the above). all i get is a known ip address for all my devices, with the ability to connect to them if they have an ssh server running. when i am outside the primary benefit is that i can tell which devices are online.

15155

This feature isn't enabled by default.

miunau

this is for teams where you don't want to create passwords or keep track of ssh keys for everyone by hand. it greatly simplified our server usage as we can simply ssh user@machine and it just works. you can create access controls for it as well.

oliyoung

> Sounds a bit like a fancier ngrok.

Well, yes and no.

You can use it like ngrok, and I'm sure you could configure wireguard and ngrok to give you something similar to what Tailscale does, but Tailscale does it out of the box, with polished and well built client and server apps.

I'm no infra guy, I'm just a former front-end eng, but it gives me the confidence to expose media centres and file servers etc to "the wild" without it being public.

Using Jellyfin to watch content from my home server on my iPad while I'm away from home is as "easy" as Disney or Netflix with Tailscale, just installed the clients and servers and .. voila?

mh-

I was an infra guy early in my career, and I'm still savvy, and I still prefer using Tailscale. It's very polished and reliable.

But personally, I'm past the point of wanting to fiddle with things like this and would much prefer them to just work out of the box.. so I can fiddle with the things I wanted to, and not end up down a (personally) unenjoyable rabbit hole.

No judgment on people who do enjoy it, though! I used to, and maybe I will again at some point.

Larrikin

Having all your mobile traffic routed through AdGuard Home (or PiHole) is a game changer. It's also nice using an exit node through my home network whenever I am on public wifi.

burnt-resistor

Plex already supports remote access via UPnP. https://support.plex.tv/articles/200289506-remote-access/

15155

Tailscale is able to hole punch in scenarios where UPnP is disabled (just good practice) as well as many NAT environments.

c0wb0yc0d3r

To me WireGuard is safer than exposing services directly to the internet.

burnt-resistor

Sure, it's pretty simple. I had WG provided by an Deciso OPNsense router with an automatic VPN profile on most user devices. All of my infrastructure also had PKI. (I moved recently and have yet to set it up again.)