this post was submitted on 09 Jun 2025
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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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[–] chameleon@fedia.io 7 points 4 days ago (3 children)

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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[–] bonsai@lemmy.dbzer0.com 6 points 2 days ago (4 children)

I never really understood the point of using Tailscale over plain ol' WireGuard. I mean I guess if youve got a dozen+ nodes but I feel like most laymens topologies won't be complex beyond a regular old wireguard config

[–] jbk@discuss.tchncs.de 6 points 2 days ago (1 children)
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[–] Jason2357@lemmy.ca 5 points 2 days ago

NAT punching and proxying when a p2p connection between any 2 nodes cannot be achieved. It’s a world of difference with mobile devices when they always see each other, all the time. However, headscale does all that.

[–] _TheLoneDeveloper_@sopuli.xyz 4 points 2 days ago

Same thing here, either tailscale selfhosted or Netbird selfhosted I'd the way to go for all the nice features, having the free tier or tailscale for personal data never sounded right to me.

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[–] ohshit604@sh.itjust.works 6 points 3 days ago* (last edited 3 days ago)

So glad my router supports WireGuard/OVPN server hosting, doing it this way also relieves resources off your homelab and for whatever reason your homelab shuts off or loses network access you can at least rely on your router to re-establish the VPN server without further intervention.

[–] Mordikan@kbin.earth 5 points 4 days ago (9 children)

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?

[–] tequinhu@lemmy.world 6 points 4 days ago (19 children)

Yup, I don't know if that is OP's intention, but I would agree myself with the complaint that "Tailscale is a business"

The way I see it, if it's a business it must generate revenue (either now or down the road), and that is enough to have me worried. I do have a Tailscale registration, and the way they approach email communication is already a yellow flag to me (too many ad emails)

[–] irmadlad@lemmy.world 4 points 3 days ago (2 children)

yellow flag to me (too many ad emails)

Weird. I'm not saying you're lying, but besides the registration email, and onboarding welcome email, I can't think of any others I've received from Tailscale. In fact, I just did a search of my email client, and those were the only ones I've received.

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[–] Ulrich@feddit.org 5 points 4 days ago* (last edited 3 days ago) (7 children)

That's pretty standard in a business life-cycle, though

I don't know where people ever got the idea that normal = acceptable. I hear this used to justify all sorts of awful crap. It was only ever normalized because users were apathetic.

And what about the Linux Foundation? They are funded through private equity. Should you consider switching away because of that?

Does The Linux Foundation have complete control over Linux?

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[–] LiveLM@lemmy.zip 5 points 3 days ago

I always knew it was too nice to stay non-shitty forever.
Guess it's time for me to pester my ISP to let me open some ports

[–] dieTasse@feddit.org 5 points 3 days ago (1 children)

Question: if I setup Headscale on my network, I would have to open a port on my router to connect to it right? And also if I setup Headscale with some cloud provider, could they theoretically go and use the setup to get to my home network? I know its unlikely, I just mean if the technology is like e2e from clients to my home network, or if the cloud headscale 'centre' would be also an unguarded entry point (from the perspective of cloud admins). I hope I am clear 😀 Thanks (btw you probably guess why I currently use Tailscale 😀)

[–] avidamoeba@lemmy.ca 6 points 3 days ago* (last edited 3 days ago) (1 children)

if I setup Headscale on my network, I would have to open a port on my router to connect to it right?

The way I understand it is:

I would have to open a port on my router to connect to it right?

Yes

if I setup Headscale with some cloud provider, could they theoretically go and use the setup to get to my home network?

If they are able to authorize their own node to your Headscale server, then their node gets on your network. If they take over the Headscale node, they might also be able to access your network, either by changing Headscale's config to auth another node or perhaps if the Headscale node is part of the network, which it might be, I don't recall. But I think that's immaterial. If someone takes over the Headscale machine, they can get on your network either way.

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[–] gemappliedfax@lemmy.zip 4 points 4 days ago

Meh. I will keep using it

[–] Goretantath@lemmy.world 4 points 4 days ago (3 children)

Didnt even work for me, i use mullvad so if i wanted to use tailscale on my android to connect to my desktop, it wants me to disable mullvad unlike on my desktop..

[–] milicent_bystandr@lemm.ee 5 points 3 days ago (2 children)

I think that's because both work on Android by being a VPN, and the system can't handle doing two vpns simultaneously

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