How I use Tailscale

https://chameth.com/how-i-use-tailscale/

by aquariusDue • 12 months ago

382 101 12 months ago

sixothree2• 12 months ago

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-bee2• 12 months ago

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.

sixothree2• 12 months ago

Thanks!

th0ma5• 12 months ago

Straight WireGuard to a single point is completely not noticeable.

8n4vidtmkvmk• 12 months ago

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?

oliyoung• 12 months ago

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-3• 12 months ago

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.

elcritch4• 12 months ago

It's pretty handy to setup an exit node on your home network so that when you go abroad you can still watch your streaming services too!

More importantly you can use it to access your bank or other services which often block non-US IPs. It's saved me a few times in the last year or two.

Larrikin• 12 months ago

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-resistor2• 12 months ago

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

c0wb0yc0d3r• 12 months ago

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

151552• 12 months ago

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

em-bee2• 12 months ago

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.

151552• 12 months ago

This feature isn't enabled by default.

miunau• 12 months ago

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.

jaxxstorm• 12 months ago

I wrote a POC for using Tailscale serve and funnel similarly to ngrok here:

https://github.com/jaxxstorm/tgate

thrown-0825• 12 months ago

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.

redat00• 12 months ago

Neat way to use Tailscale !

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

abdusco• 12 months ago

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 -

mh-3• 12 months ago

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.

modernpacifist• 12 months ago

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.

tptacek• 12 months ago

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

rendx• 12 months ago

Even without CT, services on standard ports will quickly be discovered on IPv4.

On a computer with a gigabit connection, ZMap can scan the entire public IPv4 address space on a single port in under 45 minutes.

gitgud• 12 months ago

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-h4• 12 months ago

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

moontear• 12 months ago

Yes. Yes, of course they do. Check for example https://crt.sh with your domain name to see the glorious public history of everything the certificates tell about your domain.

Jnr2• 12 months ago

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.

j452• 12 months ago

Another approach I’ve seen is to route public access from Traefik/nginx through a single Cloudflare tunnel instead, and Tailscale/Headscale can be left for private network and server access.

The traefik box can have the single Cloudflare tunnel , and tailscsle can hang out behind the scenes.

This way tailscale funnel doesn’t need to be public.

There is the self hosted Cloudflare alternative that’s escaping my mind right now too.

0xCMP• 12 months ago

I don't see why people don't just run their own CAs more for private stuff.

If exposed for others I think the wildcard cert is also what I did, but most tutorials have you issuing certs via ACME for internal or local-only things which doesn't even need to happen.

I personally run my own CA and even setup an ACME server and internal DNS. Nobody knows what I am doing there.

nyrikki• 12 months ago

It was common to set up your own CA at one point, especially when DNS management was more manual, However it presented a huge attack surface and was challenging to manage.

A compromised private CA can lead to widespread breaches, affecting various systems and applications that rely on its certificates.

The CAB forum working groups being explicitly prohibited from working on private networks (at least historically) and market incentives also produced a situation where you can't really reduce the blast radius.

ECS1 attacks on AD CS is probably the best publicly documented case for further research.

The happy path is often manageable, but still complex, bland any mistake will result in huge risks.

maccard• 12 months ago

For me, the value proposition isn’t there. I can get a wildcard domain signed from let’s encrypt and it works out of the box on every device, and you don’t have to deal with the fact that some/many appps will ignore your OS certificate rules.

exac• 12 months ago

All the dev servers I've used over the past 10 years come with warnings that they're not security hardened, so I'd be wary of using `tailscale funnel` even though it is awesome to share like that so easily.

mlhpdx• 12 months ago

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

Lammy5• 12 months ago

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 :)

mcsniff• 12 months ago

This comment should really be much higher.

xyzzy_plugh• 12 months ago

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.

Lammy5• 12 months ago

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?

Respectfully, you are failing to appreciate the full scope of the problem. It doesn't matter what Tailscale do with the data. The log contents don't matter at all, only the fact that a network connection was made. Every network connection you make creates metadata about you, and the Internet itself — the path between me and Tailscale's logging endpoint — is always listening.

Think what conclusions can be drawn about a person's behavior from a log of their network connections. Encryption doesn't matter, because we're just talking about metadata; each connection's timestamp, source, destination, and port. Think about the way each additional thing-which-makes-network-requests increases the surveillance value of all the others.

Straight away, many people's NTP client tells the network what OS they use: `time.windows.com`? Probably a Windows user. `time.apple.com`? Probably Mac or iOS. `time.google.com`? You get the idea. Yeah, anyone can configure an NTP client to use any of those hosts, but the vast vast majority of people are taking the default and probably don't even know what NTP is.

Add a metadata point: somebody makes a connection to one of the well-known Wi-Fi captive portal detection hosts around 4PM on a weekday? Maybe somebody just got home from school. Captive portal detection at 6PM on a weekday? Maybe somebody just got home from work. Your machines are all doing this any time they reconnect to a saved Wi-Fi network: https://en.wikipedia.org/wiki/Captive_portal#Detection

Add a metadata point: somebody makes a network connection to their OS's default weather-widget API right after the captive-portal test, and then another weather-API connection exactly $(DEFAULT_INTERVAL} minutes later? That person who got home is probably still home.

Anyway, you get the point that this stuff adds up! The problem with Tailscale is that its default behavior exposes metadata about entire additional classes of traffic in addition to all the examples I just mentioned that my devices were already leaking. Tailscale would have me start telling the Internet “hey I'm here and doin' stuff!” every time I read or write any file on my NAS, every time I use Steam Link remote play over LAN, every time I SSH or RDP into any of my other machines.

The free “Personal” tier is limited to only 3 users but 100 devices, so it's normal and expected to set it up the client on any and every computer you own: https://tailscale.com/kb/1154/free-plans-discounts#personal-...

My behavior would be exposed to every layer of service provider along the way: my ISP, my ISP's ISPs, the cloud provider Tailscale use to host their surveillance endpoint, Tailscale themselves if they so choose, whatever creepy secret spy implants we're not allowed to know about. No thanks! If you want to be private, you must be silent.

benreesman• 12 months ago

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.

mac-attack• 12 months ago

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.

This is the exact point where our conclusions diverge.

Why are they sending themselves so much "useless" data-intensive logs by default, from their non-paying clients that accounts for roughly ~95% of the userbase and from a profitable business perspective, largely ineligible for troubleshooting support? For me, the only logical conclusion is that the data is valuable to them.

As someone who also cares about privacy, hear are a few things that IMO suggest that free customers' logs are a part of their business model:

* Their documentation has plenty of references to security, but no references to privacy outside of the privacy policy.

* They have all but eliminated any revenue stream from average user when they made an unsolicted announcement that they upgraded their free plan to allow 100 devices and 5 users.

* The content they sponsor for marketing/advertising seems targeted for consumers instead of networking professionals. I don't see Cisco and Palo Alto Networks sponsoring every Linux/self-hosting podcast or YouTube channels for example.

* Even the flag-name for turning off logging is mild deterrent based on what you will lose (`--no-support`) as opposed to being neutral '--no-logging' or truly descriptive like most FOSS companies that are not pushing an ulterior motive such as '--no-analytics'.

* logs cannot be disabled for phones

* In my experience, disabling logs was perhaps the only thing that was not configurable through the GUI

I'm into privacy and still relatively new on the networking scene thanks to setting up OpenWrt on my router. Am I correct that when tailscale updates/hijacked resolv.conf, subsequent DNS resolution is passed onto them on visited websites even when tailscale is not being used? No, they can't "read" your traffic, but if I understand things right, they know every website you visited and for how long, which is more than enough data for a rich marketing profile. That was my takeaway before I jumped ship for a self-hosted solution.

My understanding is that they have the holy grail of data because they are getting all of your LAN, WAN and mobile network traffic. I'm not aware of (m)any companies whose business model allows access to all three? It's like if your ISP and your Mobile Network had a baby on your local server, and that baby reports every website you visit.

jononor• 12 months ago

Logging everyones network data/metadata would likely be illegal under employment law in Norways. Other European countries may have same/similar rules. GDPR may also apply. So be careful with how broadly you apply that default.

jen729w• 12 months ago

See their blog post about this from last week.

https://tailscale.com/blog/tailscale-privacy-anonymity

# What Tailscale isn't: an anonymity service

Tailscale is a secure connectivity tool that puts the highest value on the privacy of your packets. But we made an intentional choice from day one that we weren't going to try to be an anonymity tool. Quite the opposite in fact! We're an identity-centric network.

Anonymity tools, like Tor, need to be architected very differently. They trade away speed to reduce traceability. They are hard to inspect and diagnose and debug, as a feature. They make enemies, both political and corporate. They are inherently hard to audit and control, by design. In short, they are the exact opposite of what you want your corporate (or even homelab) network to be.

We believe anonymity tools are essential to safe network infrastructure and a free society. But, those tools are made by other people.

…

But if you’re looking for complete anonymity online, Tailscale is not the tool for you. Y'all, we're an identity-centric network with a centralized control plane. You should assume law enforcement can easily find out that you use Tailscale. Tailscale packets are pretty easy to detect, so you can assume they could know, through ISP logs, the shape and size of data you send between different nodes in different places (albeit without knowing the decrypted packet contents). You should assume they can correlate that flow metadata with your login identity.

hiimkeks• 12 months ago

Open and Close events are not related to identity or anonymity, so that post isn't in itself relevant. It does show that the team is very pragmatic, though.

I get why they capture this data, and by doing so they managed to build an exceptionally great service. But I also understand why one would be uncomfortable with exposing this data.

63stack2• 12 months ago

This isn't relevant to what you were replying to. Parent comment is complaining that there are logs being sent out about what is happening on his private network, he's not expecting anonymity on the internet like Tor (which is what your link describes).

jonathantf2• 12 months ago

You do get support if you're a free user, it's just best effort and via e-mail only.

ezst• 12 months ago

I think I "get" what tailscale is about, what I don't get is how much of it is re-implemented and available out of the box in headscale. I already do most of the things mentioned in the article (from hand-rolled WG, Apache and firewall configurations), so this level of centralised automation and orchestration has some appeal, but I'm not willing to hand over the keys to my entire network to them and would rather keep things in-house.

And on the topic of headscale, some people bring up netbird as an alternative. Netbird gets some immediate sympathy from me as they put lots of emphasis opensource and self-hosted, but I'd be curious to see how they compare for the use-cases described in the article.

m11a• 12 months ago

I don't know enough about networking as I should, so to plug for my gap in knowledge, I generally prefer to use more comprehensible (to me) forms of security. And a feature like this:

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.

kinda worries me (given also IP spoofing is possible?), compared to SSH keys whose mechanism is more obvious and thus easier to trust.

I definitely like the idea of Tailscale as an extra layer of protection, but I'm not sure I'd loosen existing protections while using it, whereas many Tailscale articles often present it as a panacea for internal-network-over-the-internet security. Are my concerns misplaced?

codethief3• 12 months ago

kinda worries me (given also IP spoofing is possible?),

It's not, Tailscale authenticates incoming connections. (Note that we're not talking a regular SSH connection to the server's public IP here. You'd connect to the server's SSH daemon through Tailscale.)

elcritch4• 12 months ago

Connections are also encrypted with the wire guard protocol using a per-device private key.

raesene92• 12 months ago

One useful additional aspect to Tailscale that I've not seen mentioned so far, is the integration with Mullvad.

Using that you can get the benefit of their network servers, appearing just as standard Tailscale exit nodes, which is handy if you need to geo-shift traffic at all.

oulipo• 12 months ago

Can you give more details for the un-initiated? What is Mullvad? How and why would you use this feature?

Is it to use it as a kind of VPN to make traffic "appear" from any country, and, eg, watch Netflix?

raesene92• 12 months ago

Indeed, Mullvad is a VPN provider (https://mullvad.net/en) they provide several privacy focused services including a VPN and a browser.

Using Mullvad (or other VPN products) allows someone to make their traffic originate from specific countries, which can allow for testing to see what it'll look like from different countries, or to access content which is restricted to people in a specific country. It can also allow for bypassing age check restrictions that apply to specific geographies (e.g. the UK)

Integrating it with Tailscale makes it easier to use (if you're an existing tailscale user) as instead of having to install and manage a separate product, it integrates with your existing tailscale setup, allowing you to dynamically choose a mullvad exit node in a give country, and then your Internet traffic will appear from that country.

(that all sounds somewhat ad-like but I'm not in any way affiliated with Tailscale or Mullvad apart from being a user (Tailscale did give me a nice hoodie one time for writing a blog though ))

codethief3• 12 months ago

One useful additional aspect to Tailscale that I've not seen mentioned so far, is the integration with Mullvad.

Indeed, this saved my butt earlier this year when I was at Qatar airport and they tried to MITM most of my connections (including to mullvad.net). Luckily, they didn't MITM tailscale.net, so I could log in, enable Mullvad, and thereby secure my entire traffic.

precommunicator• 12 months ago

Are you sure they weren't just trying to redirect you too a capture portal?

marcogarces• 12 months ago

if you guys love Tailscale, perhaps take a look at NetBird, an open source solution, which also has a commercial offer. Really recommend this one

user3939382• 12 months ago

Are people using this because they don’t want to configure dynamic DNS and NAT?

elcritch4• 12 months ago

Yes, but more so as a VPN. It's much easier than any traditional VPN to setup.

_1tem• 12 months ago

For me, the benefit was simple: I blocked off ssh and Postgres on my production server from the public internet, making it such that these are only accessible from my development machine and other servers. Yet from inside the tailnet I can still talk to Postgres as if it was on LAN. I’m not sure of any easy way to do this without Tailscale.

bornfreddy• 12 months ago

Any VPN (including WireGuard) would allow you to do the same, and this in indeed how the systems are usually set up. Tailscale just makes the setup a bit easier, though for this use-case not by much, imho.

jncfhnb• 12 months ago

I just wish Tailscale let you use taildrop to directly send files to other people

codethief3• 12 months ago

For a long time I didn’t bother with any kind of ACLs within my Tailscale network. […] Then one day a thought hit me. […] 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.

I'm a happy Tailscale user but I'll keep saying this whenever Tailscale comes up: We need a way to `tailnet lock` (sign) not just the tailnet nodes but also the tailnet config (ACLs). Otherwise the above scenario of an attacker taking over the entire network is still possible even if you set all ACLs correctly. All it takes is for an attacker to take over the coordination server (to manipulate ACLs) and a single tailnet node. (Which, if you run Headscale, might even be the same machine.)

Until this is fixed I am not going to trust Tailscale with authenticating connections too much and will trade in convenience for defense in depth.

EVa5I7bHFq9mnYK• 12 months ago

My primary use of tailscale is as a VPN. I have exit VPSes in 4 different countries, so usually at least one of them is not blocked from or to where I am trying to connect.

How I use Tailscale

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