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Tailscale raises $100M

tailscale.com

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Re: Tailscale raises $100M

#81

For anyone else who wonders wtf tailscale is: > Tailscale is a VPN service that makes the devices and applications you own accessible anywhere in the world, securely and effortlessly. It enables encrypted point-to-point connections using the open source WireGuard protocol, which means only devices on your private network can communicate with each other. It seems to take care of key distribution, nat-traversal, authen…

I thought that Tailscale was pretty interesting.

Avery Pennarun, its CTO, is somebody whose judgment I am used to trusting.

Then I learned that to use it, I would be dependent on authenticating using a login on one of the unaccountable internet behemoths who could take away my account for any random reason or no expressed reason at all.

No, thank you.

Re: Tailscale raises $100M

#82
post #27

Earlier quoted context omitted.

From the website: What if we all just had a static IP address, and a DNS name? …and the address migrated around the world with you? …and you could connect to any of your devices no matter where they were? Does this not promote the destruction of anonymity on the Internet?

I think you've got a fundamental misunderstanding of what Tailscale does. It's all about accessing your own devices. You don't need or want anonymity in that case. They are not a general purpose VPN service, and can't even be used as one.

No, I think you misunderstand that companies like this have huge visions, not tiny one like "just your own devices".

They are claiming they are on the road to "fix the internet", their own words.

Re: Tailscale raises $100M

#83
post #9

With such a huge investment comes the obligation to eventually pay it back. Is this another one of my favourite tools going the way of Dropbox, 1Password and all other companies that were formed around what should be a platform feature, which took on way too large investment sums and were eventually forced to become the everything, losing sight of their core values? I sincerely hope not, but there's so much bad prece…

I haven't really felt like 1Password's product materially strayed from the original mission. If anything, I'm even more delighted with the team functionality, shared vaults, quick keyboard access in 1Password 8, etc. I wouldn't put them in the Dropbox bucket. Also, I think the value Tailscale provides is fairly unique and far from obviously a platform feature like file storage and perhaps even password management.

1Password went from being buy once upgrade forever to SaaS. A lot of folks bought back when that was the package (and business model) so it's viewed relatively negatively here from some folks. I don't blame them, but also, I think 1Password is a success. I just don't think they'd have been viable under their original business model.

Re: Tailscale raises $100M

#84
post #43

Tailscale is my favorite (product) discovery of 2022. I initially set it up to use as a VPN to get around a misbehaving corporate firewall and accidentally realized it solved a whole bunch of other problems I didn't realize I had. Usually a new product doesn't even live up to the intended use case and so TS is really anomalous IMHO in how good it is. - SSH'ing into a raspberry pi I have at home that does random IoT s…

I've been using it since last summer to SSH to my pi too. Huge relief in terms of securing it. Easy to install and it just works. I'm not particularly savvy either. My only complaint is that if you use it on your phone (iphone 11) and forget to turn it off it drains the battery like crazy.

When I tried Tailscale it seemed to have high CPU problem in general under reasonable load. I don't remember the numbers, but it made me uncomfortable to use it in my low powered servers. I wonder if this is the consequence of being a userspace program unlike wireguard kernel module.

Re: Tailscale raises $100M

#85
Tailscale is absolutely amazing for accessing local first platforms (like home assistant and jellyfin). Sure, I can set up wireguard, but Tailscale is plug in play. Biggest gripe is that it messes with my DNS like nextDNS on iOS.

Re: Tailscale raises $100M

#86
post #39

Earlier quoted context omitted.

Tailscale is one of the ways you can restore the end-to-end connectivity principle that IP introduced and that NAT destroyed.

This is kind of overstated. Even if everyone went IPv6 and gave every device a public IP address, pretty much every network would have a firewall that behaved just like NAT.

This fact must be bundled everywhere someone mentioned "IPv6 will allow direct connectivity again". While NAT isn't a fully-functional firewall, it did do things that a firewall in a router would do. What equipment have proper IPv6 firewalls? Routers, that's who.

Re: Tailscale raises $100M

#87

Every time I've looked at setting up distributed VPN I've wanted layer 2, I haven't used WireGuard yet but apparently it's layer 3. I would love to be able to connect remotely and have my newly connected machine act like just another machine on the LAN. That in turn makes all kinds of other network-related operations simpler and homogeneous, in that the remote property of the connected machine(s) is abstracted away.

Check out ZeroTier. I believe it fills the same needs as Tailscale, but with layer 2.

Re: Tailscale raises $100M

#88
post #38
post #10

> For people who believe there’s a catch — and most still do — then I don’t know how to write a blog post or hire a marketing or sales team to change their minds. I think the catch is that (at least at the free level) one must trust an identity providers. For many companies that's probably fair enough, but for high-security companies and private individuals one absolutely cannot trust anything running outside of one'…

Tailscale will let you use any SAML or OIDC provider you like in the Enterprise plan (presumably because of the cost of supporting the long tail of nonsense IdPs will produce). (Disclosure: I'm a (small) investor via Latacora's sibling fund, Lagomorphic.)

Semi-related question: did Latacora or @tqbf ever open source their Go-based SAML IDP: https://twitter.com/tqbf/status/938501701526487040

(That tweet I think was a teaser saying it was coming. I subsequently looked for it a few times and never found it, but maybe plans changed, or maybe I just failed to find it).

Re: Tailscale raises $100M

#90

Earlier quoted context omitted.

I haven't really felt like 1Password's product materially strayed from the original mission. If anything, I'm even more delighted with the team functionality, shared vaults, quick keyboard access in 1Password 8, etc. I wouldn't put them in the Dropbox bucket. Also, I think the value Tailscale provides is fairly unique and far from obviously a platform feature like file storage and perhaps even password management.

Indeed, 1Password is practically a utility at this point, as far as I'm concerned. I really like the direction they're heading and they're solving some pretty tricky problems without compromising on security, predominantly in the enterprise domain. The experience is the same regardless of whether you're an enterprise user or a personal or family user. It's polished enough that my grandma can use it.

1password took away the ability to have offline vaults, so i don't know how you can say they didn't compromised on security, since they cut off the most secure way you can store your vault chasing the solving of the tricky problem of monetizing a key value store.
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