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submitted 1 week ago* (last edited 1 week ago) by avidamoeba@lemmy.ca to c/selfhosted@lemmy.world

Corporate VPN startup Tailscale secures $230 million CAD Series C on back of “surprising” growth

Pennarun confirmed the company had been approached by potential acquirers, but told BetaKit that the company intends to grow as a private company and work towards an initial public offering (IPO).

“Tailscale intends to remain independent and we are on a likely IPO track, although any IPO is several years out,” Pennarun said. “Meanwhile, we have an extremely efficient business model, rapid revenue acceleration, and a long runway that allows us to become profitable when needed, which means we can weather all kinds of economic storms.”

Keep that in mind as you ponder whether and when to switch to self-hosting Headscale.

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[-] HelloRoot@lemy.lol 156 points 1 week ago

a long runway that allows us to become profitable when needed

Switch to self-hosting headscale when they enshittify in an attempt to become profitable, duh

[-] three@lemmy.zip 47 points 1 week ago

Been meaning to do this. Tailscale was just there and easy to implement when I set my stuff up. Is it relatively simple to transition?

[-] kratoz29@lemm.ee 23 points 1 week ago

I mainly use Tailscale (and Zerotier) to access my CGNATED LAN, headscale will require me to pay a subscription for a VPS wouldn't it?

I really envy the guys who say only use them because they're lazy to open ports or want a more secure approach, I use them because I NEED them lol.

If (when?) Tailscale enshitify I'll stick with ZT a bit until it goes the same way lol, I started using it 1st, I don't know if ZT came before Tailscale though.

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[-] lka1988@lemmy.dbzer0.com 89 points 1 week ago* (last edited 1 week ago)

Tailscale never sat right with me. The convenience was nice, but - like other VC-funded projects - it followed that ever-familiar pattern of an "easy" service popping up out of nowhere and gaining massive popularity seemingly overnight. 🚩🚩🚩

I can't say I'm surprised by any of this.

Would you rather a difficult and hard to use program?

Easy to use means people will want to adopt it, and that's what VC companies want. Nobody wants to pay millions of dollars to make a program that nobody wants to use.

[-] lka1988@lemmy.dbzer0.com 54 points 1 week ago* (last edited 1 week ago)

My problem isn't directly with the programs - my problem lies with VC funding in general. Because they will come back for their money, and the project will inevitably enshittify and shove out enthusiasts in the never-ending search for infinite money.

The solution is getting rid of VC bullshit entirely. But we all know that will never happen.

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[-] potustheplant@feddit.nl 15 points 1 week ago

Maybe this is a pet peeve but it's a vpn tool that forces you to log in with an "identity provider". Yeah, no thanks.

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[-] httperror418@lemmy.world 76 points 1 week ago

I'm unsure if it has been mentioned, but a similar tool which is open source (you can run the backend unlike tailscale), netbird

https://netbird.io/

[-] couch1potato@lemmy.dbzer0.com 15 points 1 week ago

Headscale is the tailscale backend server

[-] avidamoeba@lemmy.ca 12 points 1 week ago

Well not "the" backend server but "a" different backend server. As far as I know Headscale is a separate implementation from what Tailscale run themselves.

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[-] fmstrat@lemmy.nowsci.com 52 points 1 week ago* (last edited 1 week ago)

Join our Discord server for a chat and community support.

Sigh...

And even worse:

Everything in Tailscale is Open Source, except the GUI clients for proprietary OS (Windows and macOS/iOS), and the control server.

[-] drmoose@lemmy.world 50 points 1 week ago

everything is open source except half of all things.

Lol

[-] heals@discuss.tchncs.de 14 points 1 week ago

To be fair, anything the GUI clients do can be done with the CLI which is still open source and on all desktop platforms and headscale is literally their open source control server.

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[-] Wahots@pawb.social 44 points 1 week ago

Are there better alternatives? I was planning on using tailscale until now. :P

[-] avidamoeba@lemmy.ca 53 points 1 week ago

For me personally, the next step is using Headscale - a FOSS replacement of the Tailscale control server. The Tailscale clients are already open source and can be used with Headscale.

Someone else could give other suggestions.

[-] JoMiran@lemmy.ml 12 points 1 week ago

I've been meaning to switch from Tailscale to Headscale but I have been to busy. Do you have any instructions, write-ups/walk-thrus you could recommend to set this up? I have three sites with 1GB internet I can use. One has a whole house UPS but dynamic IP, another has a static IP but no UPS, and the third is Google fiber with no UPS, but I can use the app to get the current IP anytime. I also own a number of domain names I could use.

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[-] MangoPenguin@piefed.social 26 points 1 week ago* (last edited 1 week ago)

Wireguard if you're just using it yourself. Many various ways to manage it, and it's built in to most routers already.

Otherwise Headscale with one of the webUIs would be the closest replacement.

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[-] exu@feditown.com 21 points 1 week ago

A bunch really, Headscale with Tailscale client, Nebula VPN, Netmaker, Zerotier.

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[-] candyman337@sh.itjust.works 12 points 1 week ago

I use the built in wireguard VPN in my router. If you just need local network access elsewhere it's usually really easy to setup if your router provides it. I would look into it!

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[-] pulsewidth@lemmy.world 36 points 1 week ago

I think I'll just keep using tailscale until they start enshittifying, and then set up a Headscale instance on a VPS - no need to take this step ahead of time, right?

I mean, all the people saying they can avoid any issues by doing the above - what's to stop Tailscale dropping support for Headscale in future if they're serious about enshitification? Their Linux & Android clients are open source, but not IOS or Windows so they could easily block access for them.

My point being - I'll worry when there is something substantial to worry about, til then they can know I'm using like 3 devices and a github account to authenticate. MagicDNS and the reliability of the clients is just too good for me to switch over mild funding concerns.

[-] avidamoeba@lemmy.ca 14 points 1 week ago

Yeah, as I said, it's a friendly reminder. I'm personally probably doing it this year. It's entirely possible that enshittification could come even years from now. It all depends on how their enterprise adoption goes I think. The more money they make there, the longer the individual users are gonna be left unsqueezed.

[-] cooopsspace@infosec.pub 25 points 1 week ago* (last edited 1 week ago)

Friendly reminder that Tailscale is VC-funded and driving towards IPO

You know what's to come.

The answer to the question is immediately. Or switch to OpenZiti or Pangolin even.

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[-] 30p87@feddit.org 24 points 1 week ago

What's the benefit over just WG?

[-] Starfighter@discuss.tchncs.de 39 points 1 week ago* (last edited 1 week ago)

You dont need to manually handle the WG config files. This isn't really an issue when it's just you and your two devices, but once you start supporting more people, like non-technical family members, this gets really annoying really quickly.

Tailscale (and headscale) just require you to log in, which even those family members can manage and then does the rest for you. They also support SSO in which case you wouldn't even have to create new accounts.

[-] avidamoeba@lemmy.ca 15 points 1 week ago

Easier/zero configuration compared to manual WG setup. Takes care of ports and providing transparent relay when no direct connection works.

[-] lepinkainen@lemmy.world 11 points 1 week ago

Your tech illiterate grandma can set it up. It’s that easy.

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[-] rarbg@lemmy.zip 24 points 1 week ago

Nerds stop recommending corporate crap: challenge: impossible

[-] ChickenAndRice@sh.itjust.works 19 points 1 week ago

If I host headscale on a VPS, is that as seamless of an experience as Tailscale? And would I miss out on features, like the Tailscale dashboard? How does the experience change for me (an admin type) and my users (non-technical types)?

[-] MangoPenguin@piefed.social 11 points 1 week ago* (last edited 1 week ago)

There are some community webUIs for Headscale, headplane in particular looks pretty good: https://headscale.net/stable/ref/integration/web-ui/

I'm not sure otherwise how different the experience would be.

[-] couch1potato@lemmy.dbzer0.com 1 points 5 days ago* (last edited 5 days ago)

I actually did this instead of tailscale first; installing tailscale on a pfsense router was a challenge, iirc i had to find and install the freebsd tailscale pkg from the command line because the plugin doesn't give the option to connect to a non-tailscale control plane.

After I did that and connected to my headscale server (on my vps) I could ping pfsense's local ip over the tailnet, but couldn't get any traffic out from pfsense. Turns out I had forgotten the pfsense tailscale plugin automatically sets up outbound rules for you.

That was a rabbit hole I didn't feeling like falling down, so I turned off headscale and just used tailscale account and the normal pfsense tailscale plugin. But it's there and it does work fine if I ever wanted to go figure out the outbound traffic rules.

[-] Vinstaal0@feddit.nl 18 points 1 week ago

Crap, I really need to switch of Tailscale but currently it is an easy way for me to access my stuff outside of home as a temporary solution while I am on a 5G modem.

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[-] dabe@lemmy.zip 16 points 1 week ago* (last edited 1 week ago)

Am I totally off-base in thinking that MagicDNS and pluggable DNS nameserver overrides are a huge feature of tailscale?

I love that I can refer to my tailnet devices just via their machine name. I use it everywhere. And also that I can just slot in my NextDNS ID so that any device running tailscale now automatically uses that, and I don’t have to mess with my shared router settings or per device settings. Is all that actually really easy to set up outside of tailscale? Cuz if it is and I just somehow missed that when doing all my research, I’ll happily give plain wireguard or other mesh orchestrators like NetBird a go.

And I already know that mDNS is not the answer. That protocol is simply not reliable enough.

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[-] possiblylinux127@lemmy.zip 14 points 1 week ago* (last edited 1 week ago)

I'm not that worried as there are alternatives like Netbird. The underlying tech really isn't hard to replicate since Wireguard is pretty standard.

I think it would be cool if Tailscale made it into the enterprise arena.

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[-] supersquirrel@sopuli.xyz 12 points 1 week ago* (last edited 1 week ago)

pre-emptive pikachu face strike

[-] Mordikan@kbin.earth 11 points 1 week ago

Headscale is great if you like networking fun, but that aside I'm not understanding why VC funding is such a black mark to the poster. Tailscale doesn't generate meaningful revenue streams as its early-stage, so it has to secure funding to continue operations until they achieve high enough revenue to go public. That's pretty standard in a business life-cycle, though. It seems like the main complaint is that Tailscale is a business. And what about the Linux Foundation? They are funded through private equity. Should you consider switching away because of that?

[-] lka1988@lemmy.dbzer0.com 26 points 1 week ago* (last edited 1 week ago)

The problem, though, is that VC-funded projects bite off way more than they can chew from the start and have to enshittify to keep shareholders happy at that level.

Growth for the sake of growth is a fundamentally broken concept. Tailscale provides a free service that many use. They already offer a paid support tier for companies, like other certain FOSS projects do, so why not call it good there? Grow based on actual customer needs, instead of shareholder bullshit "needs" (line must go up 🙄).

[-] Feyd@programming.dev 10 points 1 week ago

Not that it is a business but is a specific kind of business. VC funded startups eyeing an IPO more often than not start doing things users are not happy with. Maybe tailscale won't, but might as well be aware what kind of company they are acknowledge there is a decent chance of rugpulls

[-] Revan343@lemmy.ca 10 points 1 week ago

It seems like the main complaint is that Tailscale is a business. And what about the Linux Foundation?

The Linux Foundation is not a business.

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[-] qjkxbmwvz@startrek.website 11 points 1 week ago

I think a lot of companies view their free plan as recruiting/advertising


if you use TailScale personally and have a great experience then you'll bring in business by advocating for it at work.

Of course it could go either way, and I don't rely on TailScale (it's my "backup" VPN to my home network)... we'll see, I guess.

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[-] lefixxx@lemmy.world 11 points 1 week ago

Yeah and steam is closed source DRM platform. Great software sometimes is worth the trade off.

[-] Uncut_Lemon@lemmy.world 39 points 1 week ago* (last edited 1 week ago)

Steam is a private company, not publicly traded and has no VC funding.

VC funding and potential IPO normally means enshittification is inevitable, as they will eventually need to make insane profits by turning the screws on its users, as their business model wasn't self sustaining.

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[-] PumaStoleMyBluff@lemmy.world 10 points 1 week ago

become profitable when needed

By what, laying off all QA and support staff and half your developers the moment a single quarterly earnings report isn't spotlessly gilded?

[-] chameleon@fedia.io 10 points 1 week ago

They also had a major ass security issue that a security company should not be able to get away with the other day: assuming everyone with access to an email domain trusts each other unless it's a known-to-them freemail address. And it was by design "to reduce friction".

I don't think a security company where an intentional decision like that can pass through design, development and review can make security products that are fit for purpose. This extends to their published client tooling as used by Headscale, and to some extent the Headscale maintainer hours contributed by Tailscale (which are significant and probably also the first thing to go if the company falls down the usual IPO enshittification).

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this post was submitted on 09 Jun 2025
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