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.

top 100 comments

sorted by: hot top controversial new old
[–] 154 points 1 year ago (18 children)

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

  • source
  • hideshow 18 child comments
  • [–] 22 points 1 year ago (14 children)

    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.

  • source
  • parent
  • hideshow 14 child comments
  • [–] 9 points 1 year ago (3 children)

    Same. I mean, I was already looking to rent a VPS, but at least there's some time so I can save money until things get weird.

  • source
  • parent
  • hideshow 3 child comments
  • [–] 7 points 1 year ago (2 children)

    Yeah, don't get me wrong, I can see value of getting a VPS, especially if you are gonna be using it for some other projects, I have had a DO instance in the past and I thinkered with WG back then BTW, but if it is only for remote accessing your home LAN, I don't feel like paying for it tbh, especially when some users get it for free (public IPv4) and it feels even dumber for me since I have a fully working IPv6 setup!

    BTW my ISP is funny, no firewall at all with it, I almost fainted when I noticed everyone could access my self hosted services with the IPv6 address and I did nothing regarding ports or whatsoever... They were fully accessible once I fired up the projects! I think I read an article about this subject... But I can't recall when or where... I had to manually set up a firewall, which tbh, you always should do and it is especially easy to do in a Synology NAS.

    Anyway, back to the mesh VPN part, if they enshitify so be it, but in the meantime we still can benefit from it.

  • source
  • parent
  • hideshow 2 child comments
  • [–] 3 points 1 year ago (1 child)

    Thats just how IPv6 works. You get a delegate address from your ISP for your router and then any device within that gets it own unique address. Considering how large the pool is, all address are unique. No NAT means no port forwarding needed!

  • source
  • parent
  • hideshow 1 child comment
  • [–] 1 point 1 year ago

    I guess so, my previous ISP also gave me IPv6 address (I could navigate using it) but I could never access my NAS services with it from an IPv6 ready network, I thought it would be the same with the newer ISP, but nope.

    Maybe some firewall is active by the ISP? I could not do much thinker back then as I used the stock modem (router) and it was heavily locked.

  • source
  • parent
  • [–] 4 points 1 year ago (9 children)

    Vps can be really inexpensive, I pay $3 a month for mine

  • source
  • parent
  • hideshow 9 child comments
  • [–] 4 points 1 year ago* (5 children)

    Same, my Hetzner proxy running NPM, with pivpn and pihole is doing all it needs to do for $3 and some change.

    My only open ports on anything I own are 80, 443 and the wg port I changed on that system. Love it.

  • source
  • parent
  • hideshow 5 child comments
  • [–] 3 points 1 year ago (4 children)

    How does WG work on the local side of the network? Do you need to connect each VM/CT to the wireguard instance?

    I am currently setting up my home network again, and my VPS will tunnel through my home network and NPM will be run locally on the local VLAN for services and redirect from there.

    I wonder if there is any advantage to run NPM on the VPS instead of locally?

  • source
  • parent
  • hideshow 4 child comments
  • [–] 3 points 1 year ago* (3 children)

    The vps is the wg server and my home server is a client and it uses pihole as the dns server. Once your clients hang around for a minute, their hostnames will populate on pihole and become available just like TS.

    You do have to set available ips to wg's subnet so your clients don't all exit node from the server, so you'll be able to use 192.168.0.0 at home still for speed.

    As for NPM, run it on the proxy, aim (for example) Jellyfin at 10.243.21.4 on the wg network and bam.

  • source
  • parent
  • hideshow 3 child comments
  • [–] 1 point 1 year ago (2 children)

    I am a newbie so I am not sure I understand correctly. Tell me if my understanding is good.

    Your Pi-Hole act as your DNS, so the VPS use the pi-hole through the tunnel to check for the translation IP, as set through the DNS directive in the wg file. For example, my pi-hole is at 10.0.20.5, so the DNS will be that address.

    On the local side, the pi-hole is the DNS for all the services on that subnet and each service automatically populate their host name on pi-hole. I can configure the DNS server in my router/firewall (OPNSense in my case)

    So when I ping service.example.com, it goes through the VPS, which queries the pi-hole through the tunnel and translates the address to the local subnet IP if applicable.

    So when I have the wg connection active and my pi-hole is the DNS, every web request will go through the pi-hole. If the IP address is inside the range of AllowedIPs, the connection will go through the tunnel to the service, otherwise, the connection will go through outside the wg tunnel.

    Does that make sense?

  • source
  • parent
  • hideshow 2 child comments
  • [–] 1 point 1 year ago* (last edited 1 year ago) (1 child)

    the VPS uses the pi-hole through the tunnel

    The VPS is Pihole, the dns for the server side is 127.0.0.1. 127.0.0.1 is also 10.x.x.1 for the clients, so they connect to that as the dns address.

    server dns - itself

    client dns - the server's wg address

    On the local side, the pi-hole is the DNS for all the services on that subnet and each service automatically populate their host name on pi-hole. I can configure the DNS server in my router/firewall (OPNSense in my case)

    Only if your router/firewall can directly connect to wg tunnels, but I went for every machine individually. My router isn't aware I host anything at all.

    So when I ping service.example.com, it goes through the VPS, which queries the pi-hole through the tunnel and translates the address to the local subnet IP if applicable.

    Pihole (in my case) can't see 192.x.x.x hosts. Use 10.x.x.x across every system for continuity.

    So when I have the wg connection active and my pi-hole is the DNS, every web request will go through the pi-hole. If the IP address is inside the range of AllowedIPs, the connection will go through the tunnel to the service, otherwise, the connection will go through outside the wg tunnel.

    Allowed ips = 10.x.x.0/24 - only connects the clients and server together

    Allowed ips = 0.0.0.0/0 - sends everything through the VPN, and connects the clients and server together.

    Do the top one, that's how TS works.

  • source
  • parent
  • hideshow 1 child comment
  • [–] 2 points 1 year ago (1 child)

    Or get something like a rapsberry-pi (second hand or on a sale). I have netbird running on it and I can use it to access my home network and also use it as tunnel my traffic through it.

  • source
  • parent
  • hideshow 1 child comment
  • [–] 10 points 1 year ago

    Bookmarking "headscale"!

    I only recently started using Tailscale because it makes connecting to my local network through a Windows VM running in Boxes on Linux a hell of a lot easier than figuring out how to set up a networked bridge.

    This sounds like a great alternative, and it looks like it can even work on a Synology NAS.

  • source
  • parent
  • [–] 79 points 1 year ago (7 children)

    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/

  • source
  • hideshow 7 child comments
  • [–] 4 points 1 year ago (2 children)

    We've implemented netbird at my company, we're pretty happy with it overall.

    The main drawback is that it has no way of handling multiple different accounts on the same machine, and they don't seem to have any plans for ever really solving that. As long as you can live with that, it's a good solution.

    Support is a mixed bag. Mostly just a slack server, kind of lacking in what I'd call enterprise level support. But development seems to be moving at a rapid pace, and they're definitely in that "Small but eager" stage where everything happens quickly. I've reported bugs and had them fixed the same day.

    Everything is open source. Backend, clients, the whole bag. So if they ever try to enshittify, you can just take your ball and leave.

    Also, the security tools are really cool. Instead of writing out firewall rules by hand like Tailscale, they have a really nice, really simple GUI for setting up all your ACLs. I found it very intuitive.

  • source
  • parent
  • hideshow 2 child comments
  • [–] 1 point 1 year ago (1 child)

    Thank you for your insight, I'm assuming the only public part is the UI and coturn (the bit that enables two clients between firewalls to hole-punch)?

  • source
  • parent
  • hideshow 1 child comment
  • [–] 2 points 1 year ago

    Yes, the underlying model is the same as Tailscale, Zerotier and Netmaker (also worth checking out, btw). Clients connect to a central host (which can be self-hosted) and use that to exchange information on addresses and open ports, then form direct connections to each other.

  • source
  • parent
  • [–] 2 points 1 year ago (1 child)

    Is there an issue with Netbird's servers at the moment? In my testing devices are connected and reach eachother, but the web admin is missing a lot of functionality compared to what's in the docs. The peer devices section is there, but everything else, user settings, rules etc, isn't showing/says I don't have admin permission (of my own account.. Lol?)

  • source
  • parent
  • hideshow 1 child comment
  • [–] 43 points 1 year ago (18 children)

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

  • source
  • hideshow 18 child comments
  • [–] [S] 53 points 1 year ago (2 children)

    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.

  • source
  • parent
  • hideshow 2 child comments
  • [–] 13 points 1 year ago (1 child)

    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.

  • source
  • parent
  • hideshow 1 child comment
  • [–] [S] 8 points 1 year ago*

    No writeups. I tried following the Headscale doc for a test last year. Set it up on the smallest DigitalOcean VM. Worked fine. Didn't use a UI, had to add new clients via CLI on the server. When I set it up for real, I'd likely setup a UI as well and put it in a cloud outside of the US. It would work at home too but any other connection would die if my home internet dies or the power does. E.g. accessing one laptop from another, or accessing the off-site backup location.

  • source
  • parent
  • [–] 26 points 1 year ago* (6 children)

    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.

  • source
  • parent
  • hideshow 6 child comments
  • [–] 1 point 1 year ago (4 children)

    I decided to experiment a bit with Headscale when the wg-easy v15 update broke my chained VPN setup. Got it all set up with Headplane for a UI, worked amazingly, until I learned I was supposed to set it all up on a VPS instead and couldn't actually access it if I wasn't initially on my home network, oops.

    I might play around with it again down the road with a cheap VPS, didn't take long to get it going, but realistically my setup's access is 95% me and 5% my wife so Wireguard works fine (reverted back to wg-easy v14 until v15 allows disabling ipv6 though, since that seemed to be what was causing the issues I've been seeing).

  • source
  • parent
  • hideshow 4 child comments
  • [–] 1 point 1 year ago (3 children)

    Why does it need to be on a VPS? It seems to work on a home network when I played around with it.

  • source
  • parent
  • hideshow 3 child comments
  • [–] 1 point 1 year ago (2 children)

    Well a VPS or an exposed service, but I feel like the latter ends up somewhat defeating the purpose anyway.

    When running locally (not exposed), it worked great until I tried to make the initial connection from mobile data - can't establish a connection to headscale if it can't reach it in the first place. Unless I'm mistaken, the headscale service needs to be publicly accessible in some way.

  • source
  • parent
  • hideshow 2 child comments
  • [–] 9 points 1 year ago (3 children)

    ive been eyeing up netbird but havnt got around to trying it yet. its fully open source at least, and theyre based in germany is anyone cares about that

  • source
  • parent
  • hideshow 3 child comments
  • [–] [S] 9 points 1 year ago (1 child)

    Just looked at NetBird, it looks suspiciously similar to Tailscale in what it does except they also got an open-source control server. They have self-hosting doc right in their web site. Looks interesting. Can't find much about the company other than it's based in Berlin and it's currently private - Wiretrustee UG.

  • source
  • parent
  • hideshow 1 child comment
  • load more comments (1 reply)
  • [–] 5 points 1 year ago

    I use Nebula. It's lightweight, well-engineered and fully under your control. But you do need a computer with a fixed IP and accessible port. (E.g. a cheap VPS)

    You can also use "managed nebula" if you want to enjoy the same risk of the control point of your network depending on a new business ;-)

  • source
  • parent
  • [–] 35 points 1 year ago (1 child)

    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.

  • source
  • hideshow 1 child comment
  • [–] [S] 12 points 1 year 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.

  • source
  • parent
  • [–] 29 points 1 year ago (7 children)

    Tailscale is great. The principle concern to me is that your super easy mesh network depends on Tailscale so if they want it they have control, and if they change their pricing or options you depend on them, and though they can't see the data you send they can see the topology of your network and where all your computers/devices are.

    I use Nebula, which is more work to set up and doesn't have some of the features, not But if you slap the 'lighthouse' (administrating node) on a cheap VPS it works great. And it has some advantages. But Nebula also troubles me: though it's fully open source and fully in your control, the documentation isn't great. Instead, you can now get "managed nebula", which puts you in the same problem as Tailscale: the company sees and controls your network topology. I fear the company (Defined Networking) is trying to push things that way. Even their android app you can't fully configure unless you use their 'managed' service.

    For now, Nebula is great, and my preferred mesh network (I looked into all the main ones). And for Tailscale you can run the administration server yourself with Headscale and be fully in your control.


    Actually I wish Tailscale the best as a profitable business. They've created a fantastic service and system. But for me, I'd rather my network be in my own hands and for my own eyes. And, as is OP's main point, once they have enough dependent users, the service might turn much worse.

  • source
  • hideshow 7 child comments
  • [–] 8 points 1 year ago (4 children)

    Netbird seemed to go in a similar way, though still good. I want to try zrok next, looks interesting

  • source
  • parent
  • hideshow 4 child comments
  • [–] 29 points 1 year ago (6 children)

    I just replaced my entire setup with base wireguard as a challenge, easier than I expected it to be, and not hard to mimic tailscale.

  • source
  • hideshow 6 child comments
  • [–] 6 points 1 year ago (1 child)

    If you just have to talk from many devices to the one server sure, but Tailscale sure makes it easy for many to many. Also if a direct connection is impossible (e.g. firewall of china, CGNAT etc) tailscale puts a relay server in the middle for you.

  • source
  • parent
  • hideshow 1 child comment
  • [–] 52 points 1 year ago* (8 children)

    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.

  • source
  • hideshow 8 child comments
  • [–] 13 points 1 year ago (4 children)

    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.

  • source
  • parent
  • hideshow 4 child comments
  • [–] 1 point 1 year ago (3 children)
  • [–] [S] 4 points 1 year ago (1 child)

    Huh, I actually didn't know this because I don't use Windows/macOS/iOS. Somehow completely missed this.

  • source
  • parent
  • hideshow 1 child comment
  • [–] 3 points 1 year ago

    Granted this is not Headscale's fault, they're just using Tailscale clients. Either way I'm glad I use a roll-your-own Wireguard.

    I and my partner also don't use those OSs, but it's more the point of using FOSS when we can.

  • source
  • parent
  • [–] 25 points 1 year ago* (1 child)

    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.

  • source
  • hideshow 1 child comment
  • [+] 19 points 1 year ago (2 children)
  • [–] 11 points 1 year ago* (1 child)

    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.

  • source
  • parent
  • hideshow 1 child comment
  • [–] 1 point 1 year 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.

  • source
  • parent
  • [–] 17 points 1 year ago (17 children)

    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.

  • source
  • hideshow 17 child comments
  • [–] 8 points 1 year ago (7 children)

    I can recommend to take a look at netbird.io

  • source
  • parent
  • hideshow 7 child comments
  • [–] 7 points 1 year ago (4 children)

    I can't. I tried it first and installed it on my phone from f-droid. After opening it up, it connected to an already existing network with other people's old machines from years ago on it. I was horrified.

    So then I tried to delete my whole account and couldn't due to an error. I sent them an email about it and they took like two weeks to respond.

  • source
  • parent
  • hideshow 4 child comments
  • [–] 3 points 1 year ago (3 children)

    Netbird isn't on F-droid

    Are we talking about the same thing

  • source
  • parent
  • hideshow 3 child comments
  • [–] 1 point 1 year ago (2 children)
  • [–] 3 points 1 year ago (1 child)

    It has never been on F-droid. I've been following the service since it started. It didn't even have a mobile app not that long ago.

  • source
  • parent
  • hideshow 1 child comment
  • [–] 1 point 1 year ago

    It's possible I misremembered and got the apk from their website or github. Doesn't change anything though.

    I just went back though my emails, I got a reply email from their CTO promising to look into it and they would get back to me, but they never did.

  • source
  • parent
  • [–] 3 points 1 year ago (1 child)

    Much more user friendly

    Json is awful for config

  • source
  • parent
  • hideshow 1 child comment
  • [–] 1 point 1 year ago*

    Crockford is a good and smart person but he really dropped the fucking ball on JSON.

    Double-quotes-only and no comments kill the whole spec for me. Extremely opinionated and dumb. I fucking hate JSON.

    My boss once sent me a machine generated config. He's terminally addicted to double-quotes (like, a fatal condition). I searched and there were 27k sequences of \".

    Edit: my point is - all that compute and network wasted, every single time the file is requested and parsed. Completely pointless waste

  • source
  • parent
  • [–] 4 points 1 year ago (8 children)

    Do you pay for a domain? They likely provide dynamic DNS (DNS). If you're lucky, they have an API for it, instead of an app, and you can configure a cronjob on your home server to run every 1-5 minutes (or more often, if your IP is super unstable!).

  • source
  • parent
  • hideshow 8 child comments
  • [–] 2 points 1 year ago (7 children)

    Yeah I can always do that, but putting stuff behind something like Tailscale is (or atleast feels) more secure than making my IP known to the public. I have a DMZ setup though so it should be fine.

  • source
  • parent
  • hideshow 7 child comments
  • [–] 3 points 1 year ago (6 children)

    Your "IP address" is already public. That's why an IPv4 address is assigned to you as a "public IP address" and you NAT to a private space. When using IPv6, everything is public.

    The key is to secure everything with access restrictions.

  • source
  • parent
  • hideshow 6 child comments
  • [–] 2 points 1 year ago (5 children)

    Well yes I know, but there is a difference between using a domain bound to me as a person and a random string of numbers that changes every 5 minutes

  • source
  • parent
  • hideshow 5 child comments
  • [–] 2 points 1 year ago (4 children)

    Chances are you've had the same public IP for a long time. Mine hasn't changed in 2 years.

  • source
  • parent
  • hideshow 4 child comments
  • [–] 3 points 1 year ago*

    @chronicledmonocle @Vinstaal0 I used to work for a dial-up ISP. Every IP is registered to an account, if you're going through your ISP (as opposed to, say, coffee shop or hotel wifi). Though the people who have the information are different (ICANN/registrar vs your internet provider), there's no anonymity in your home IP address even with CGNAT.As far as your domain, you should have privacy protection enabled so people can't find your personal info via whois.

  • source
  • parent
  • [–] 1 point 1 year ago (2 children)

    That was the case when I lived with my parents, but now it changes every 5 minutes sadly.

    So I had to shut down my Minecraft server etc for now because I am on a 5G modem which makes it really annoying to open up ports and point a domain to your IP

  • source
  • parent
  • hideshow 2 child comments
  • [–] 16 points 1 year ago* (2 children)

    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.

  • source
  • hideshow 2 child comments
  • [–] 9 points 1 year ago

    I use wireguard and have public DNS refer to private IPs.

    For example if my server is accessible at 10.0.0.1 via wireguard then I point *.myserver.mydomain.com to that IP.

    Sorry if I've misunderstood your question.

  • source
  • parent
  • [–] 12 points 1 year ago (1 child)

    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.

  • source
  • hideshow 1 child comment
  • [–] 12 points 1 year 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?

  • source
  • load more comments
    view more: next ›