Tailscale addressing concerns over potential enshittification of the platform
The evasive evitability of enshittification
Tailscale recently announced our Series C fundraise, and while we were grateful for the support, the Internet, as it does, also raised a few eyebrows — some wondering whether this meant the dreaded “enshittification” was on the horizon for Tailscale.
I have read so many posts like this, that try to explain why their company is a special case and why it could never happen to them, only to see the same thing happen again and again.
Tailscale are trying to insert themselves into the stack and become the go-to choice for this kind of networking. When their customers are dependent on it, of course they'll start extracting rent and capturing as much as they can.
That's their right, but it's also a little condescending to pretend otherwise.
Yeah, this post started as a reassurance that Tailscale wouldn't enshittify. But it turned out to just be an argument about how to avoid enshittification that boiled down to two principles:
Both are partially right and partially wrong.
For #1: Yes, making your product worse eventually harms the company. No, you can't expect CEOs to accept that as a reason to not make their product worse because even if it harms the company, short-term incentives that lead to enshittification are eventually going to become irresistible. His comment about reaching "zen" with leveled growth and profit will never stop VCs from calling in demands and favors.
For #2: Yes, founders typically "get it" more than their VC- or failure-initiated replacements. No, that doesn't mean founders are uniquely resistant to enshittification. This is your point too, and it's why I don't believe this person - they lose credibility here because they don't acknowledge they aren't special. Every tech bro out there thinks they've cracked the code to permanent tech hegemony. That exceptionalist thinking turns into enshittification, since the product-worsening or overcharging is easier to justify as temporary/necessary/not-a-big-deal (until it isn't).
And all of this doesn't explain why Tailscale specifically gets immunity if the principles are true.
So interesting post, and a lot more self-awareness than most founders which is still a little reassuring, but a lot of warning signs too.
Edit: clarity
Definitely agree with you
From my experience most companies enshitify before the IPO to juice the metrics and boost their valuations (I.e. their payout).
The fact that they aren’t doing that yet that is a positive sign.
But founders aren’t immune to suffering from billionaire brain rot and years of exposure to the constant sycophancy and wealth seems to turn nearly everyone into a greed driven money soulless vampire.
Remember when Google's motto was "Don't be evil"?
I really don't see how the enshitification could work when we have the fee version of the central servers Headscale
So yes, it could be a pay wall for some advance featuresike funnels and so on. But the primary use is secured....
There is no guarantee headscale can keep working the way it does or that it is allowed to keep existing.
Edit: FYI headscale is not at all at feature parity with what tailscale offers.
Their brilliant idea was to combine the amazing Wireguard with all the ideas from the VOIP world for performant p2p connections of mobile devices. That gave them a head start but especially with headscale existing, anyone can replicate that. Now, their business depends on being the slickest option for managing authentication, users, devices, and ACLs for businesses. The writing is already on the wall for selfhosters - we don’t really need all those features.
The article also doesn't address how tailscale could enshittify and that they won't do it.
Ur dumb.
Have you ever thought about how we're different though?
This person is desperately trying to convince themself. Once the finance capitalists gain control they will be steering the company. They don't care about long term profits if they can squeeze high short term profits. They don't give a shit about the company, especially in tech. They'll sell off any IP (or keep it for their collection) when it's time for bankruptcy and move on to the next target.
Agree. The person who wrote the article is Avery Pennarun, co-creator of tailscale. I've heard him in interview ; he's very smart, both technically, and in high picture thinking.
But... Missing the point that VC money is cursed because they don't care if your product is good, successful or a boon to others, is a bit naive.
I call them locusts. Destroy everything for their own benefit and move on to the next target.
Thats the system. Its designed like that. There are books depicting this stuff from 100 years ago.
so yadda yadda yadda, they will be enshittifying eventually?
you guessed it!
Based on their early mode and communication, I think this was always the plan. VC culture is toxic 🙄
This is excellent article on enshitification, some of the factors that can lead to it, and ways founders could think about it to hopefully avoid it. What it doesn't seem to talk about is how Tailscale intends to avoid it, now and in the future.
Better yet, why put yourself at the mercy of something that can enshittify in the first place? I've never understood why people get into selfhosting and then go right back to giving power over their network to a 3rd party again.
I don‘t think it is a binary situation: Complete self sustainability vs. full dependence on large corporations. Rather it is a spectrum and everyone feels comfortable somewhere else on it. Also I don‘t think the ends really exist, as someone else will always have power over you (you can‘t reasonably maintain everything yourself) and you can always migrate/quit from a service. Over time your position might change. For me personally I think Tailscale is a great service and for someone just starting out I would definitely recommend it. I think a lot frustration can be avoided when you don‘t set your self-hosting goals to high at the beginning. You can always update your setup later on.
Because it's a stepping stone in the learning. Using something like tailscale that just works allows you to develop skills with other software and workflows. Eventually you progress to harder things like hosting your own private VPN.
Convenience. Setting up Tailscale is easier than setting up WireGuard by yourself and dynamic dns. Not by much but enough that those who don't know how to do latter might opt for Tailscale
It amazes me that so many people obsessed about self hosting everything use this service - really asking for it.
Do you audit all the open source code you self host or trust someone is doing it for you?
Tailscale offers a valuable service and is respected and dependable. After this I'm not sure but let's see. The point is you have to put your trust somewhere and play with the convenience / privacy ratio
I think all they can really say is it's not on the near horizon, but every public company will enshittify at some point. I can't see a future where the investors will be OK for anything but going public or an acquisition by a public company. It's just a question of when, and when they start to turn the screw.
I always look for the companies that are advertising heavily. If we could see their books, I'd say the ones that spend more on marketing than engineering, product, and ops are likely the ones who will enshittify, eventually. They are building the product or service to sell later so they are trying to drum up users and corner the market.
Unfortunately, this is just about everything in the US now.
I always run headscale on my own server for my own network.
Been thinking about this for a while. What's the lift to switch to headscale? Do I need a VPS for external clients? Would a separate site work, such as a family member's house? Any other snags to worry about?
"An expansive vision that's not about money" 🤣 thanks for the laughs.
It's about creating the conditions for money later
"Expansive", great definition, thanks.
It said it was going to explain why enshittification wouldn't happen to them, but didn't.
remember kids, the "C" in series-C stands for Crap.
Huh TIL. Thought it was cock.
I've always figured that if it was free on the internet, at some point I'd have to find something else to do the same as the former free software/item. That's just the way it goes. Hardly anything stays the same.
I always operate under the assumption that if the product is free, then the user('s data) is the product
In a lot of cases yes, but things like Truenas Bitwarden are paid by enterprise users and the community versions help them with spreading word about the software and helping signal bugs etc.
Yes they can also turn to shit, but generally the consumer markt is so slim that they don;t care
Sure, but there are a lot of things you can do with the use of a good firewall, Pi-Hole, VPN, et al, you can mitigate those leaks. Anytime I fire up a new piece of software, my firewall pops up and says 'Hey bro, you really want this chatty piece of software running uninhibited on your network?' and here I go plugging holes. It's not 100%. Some software absolutely refuses to work unless it has internet access. Bluebeam comes to mind. You do what you can, and decide if the hardwired software is something you really need or not.
Not entirely the case. There are several companies that market primarily to business users that offer freebies to hobbyists -because those hobbyists sometimes eventually get to buy services for their employer.
Re-brand to "Tailsale" when?
I hope this turns out to be true but we have heard this a thousand times. ‘Don’t be evil, oh wait but profit…’
time for me to find an alternative
Headscale already exists and the Tailscale clients are open source.
Fork their project :) CLI clients are easy enough to use on PC Mac and Linux, All we need is for someone to build Android and iOS clients.
There are loads of alternatives now so it's a good time to have a look.
I've setup netmaker at home, and netbird at work They are both good solutions.
I think if I had to redo home I would swap to netbird. Both of these are fully self hosted.
Neither are as easy to setup as tailscale, but once you get over that hurdle it's fine.
Big words. I hope, though don't trust, they can live up to them. But if tailscale goes, I'm just plain fucked. Thats certainly an indicator they're worth some money to me, but there's many a FOSS project before I get to paying a VC one.
As an aside, an interesting service would be a fund allocation type thing. You donate £x, tick which services you use and the funds get divvied up by what you use. Only able to donate £10 but use a lot of services? Each service gets very little, too little to donate as an individual, so little the individual doesn't. But, on aggregate (with hundreds, or dozens of users) it would add up to a worthwhile donation. I thought of "round robin"ing my donations: pihole gets 10 this month, jellyfin the next, audiobookshelf the month after that... but yikes the admin.
Funds are donated when £x is accrued at the end of the month, and the service is maintained by earning interest on the funds held through the month. Idealistic, ripe for abuse, and out of my league to write and administrate. I promise I'd publish all the finances to keep me honest though.
Just a notice, there's also Netbird, so you won't be that fucked...
Thank you, saved. I'd still be a little but fucked, but not entirely.
I guess I should get on with learning/donating to this soon while the sun's still shining with Tailscale. Slower, more gentle transition, fuck up in some dev environment instead of my actual server. Goddamn was tailscale so easy though.
I'm not waiting for that shit to happen. I just moved over to headscale and am done with tails ale. They will enshitify, it's a matter of when, not "if".
Is headscale also closed source and in the US?
"Headscale is an open source, self-hosted implementation of the Tailscale control server."
Tailscale luckly isn't in the US
I know they are open source and 'acknowledged contribution', but have no idea where they are headquartered. Although it's very likely also US based.
Mate, this isn't a new church roof.
Your fundraisers are going to want that money back and then some. Forever.
They have enough open source code out there to make the CLI clients and server.
It could be forked right now and turned into a separate project. BSD3 license. Rerelease with modifications. A couple of multi-platform devs could manage it.
Well here it comes
This is why I really wish the "control servers" were selfhostable on the open web. Kind of similar to how you can self host a relay node for Rustdesk.
You can connect a headscale derp server to a tailscale environment.
This shit text was generated by llm, wasn't it?
Isn't this a closed-source source service based out of the US? The US government could demand a backdoor in it at anytime in a secret court and no one would know.
Why is enshitification the thing being debated?
Tailscale is Canadian.
I thought they were based in Toronto
Because this is also part of enshitification. What you mention is just another symptom of it.
Believe their servers are closed source, but the rest such as their clients are open source.
the first paragraph is not like in the post. did they rephrase it because of the "as it does" part?
this is the current version:
Tailscale recently announced our Series C fundraise. We were grateful for all the community support, but the Internet also raised a few of its collective eyebrows, wondering whether this meant the dreaded “enshittification” was coming next.
the internet archive does not show your version either: https://web.archive.org/web/20250702140430/https://tailscale.com/blog/evitability-of-enshittification
where did you get that quote from?
I think the article is pretty accurate about what to expect. The author's view is grounded in reality. They are a business, but that doesn't mean "the capitalists are in control". I would like to think commenters have researched Accel's prior fundings, but I know that is not likely. In short, they do not attempt to control companies. In 300 fundings, they have never attempted to take a majority stake in any company and do not hold majority stake in any company. They don't do acquisitions.
Accel is probably one of the few equity groups that isn't pure fucking evil. If anyone wants to pick a fight over that, fine, but at least research that company first.
"I can't think of any examples of companies that, in real life, enshittified because they were successful."
Microsoft.
EA, Blizzard, Ubisoft, The New York Times, Fox "News", Walmart, Amazon, Google...
The list is very, very big. They must just be blind as all fuck.