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Tailscale has raised $160M

tailscale.com

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Re: Tailscale has raised $160M

#281
post #231

Start looking for alternatives already. Nothing good came out of VC rounds and private equity for the end consumers ever.

I understand the cynicism. But this is counter productive. Any venture has to have a finance angle. They are not missionaries.

What's wrong with Steam (Valve) business model?

Re: Tailscale has raised $160M

#282

I've got conflicted feels about Tailscale. I love their product and a bunch of the people I know use their free tier, including myself. But their enterprise strategy destroys their good will. I can only assume it's focused on killing old school VPN products. The free tier that we love is a marketing expense. And it’s not even a conversion play. People are complaining about ~10/user/month -- add basic things that you'…

If 20$/user/month is too much, maybe you could apin up headscale and plug in your OIDC provider?

Never tried it myself, I only manage small tailnets so the free tier is fine

Re: Tailscale has raised $160M

#283

Earlier quoted context omitted.

> NAT/STUN world you were trying to avoid The clean way to build this is with firewall configuration, opening ports, and static IPs. NAT/STUN and dynamic IPs are just a hack and I don't understand why people pretend this is an acceptable solution for professional networking. Working around an infrastructure that isn't a natural law but can be changed at our will seems like a big waste of time.

> I don't understand why people pretend this is an acceptable solution for professional networking Because it IS acceptable for many cases. Many businesses don't operate in such a way as to have centralised infrastructure solely for providing internal networking, nor would they want to add the additional administrative or unnecessary routing overhead. Even locations that would traditionally be considered highly centr…

Dynamic IP addresses typically also have a forced disconnect at a regular interval. Not really what I want to host services on.

Re: Tailscale has raised $160M

#284

Earlier quoted context omitted.

> NAT/STUN world you were trying to avoid The clean way to build this is with firewall configuration, opening ports, and static IPs. NAT/STUN and dynamic IPs are just a hack and I don't understand why people pretend this is an acceptable solution for professional networking. Working around an infrastructure that isn't a natural law but can be changed at our will seems like a big waste of time.

> I don't understand why people pretend this is an acceptable solution for professional networking Because it IS acceptable for many cases. Many businesses don't operate in such a way as to have centralised infrastructure solely for providing internal networking, nor would they want to add the additional administrative or unnecessary routing overhead. Even locations that would traditionally be considered highly centr…

Also DERP relays having QOS that isn't controlled by myself and I have to hope to get bandwidth through doesn't exactly make me confident about the solution

Re: Tailscale has raised $160M

#285

Off-topic, but it makes me laugh that companies will list their “investors”, “advisors”, etc. on their company page, but not the people working there. That said, Tailscale is one of the products that just works.

Companies hide their employees, especialy the real value adding ones, for fear of them getting poached.

Re: Tailscale has raised $160M

#286
It is commendable that TS has created a market in an already crowded marketplace of VPN tools. They're competing with Palo Alto, Netskope, Check Point, and Cisco, to name a few.

One key understanding from my brief market experience is that you must build a firewall or router if you really want to own the VPN market. The way the sale is done is that the vendor goes in with the firewall, router, and switch, offering office space connectivity with the infrastructure and various network locations and upselling the VPN. This often accounts for the subpar quality of VPN software. There is a trend called SASE, which includes technologies like TS; people are questioning the enterprise value of SASE. Netskope and Cato Networks are some examples.

I believe that their enterprise journey will be challenging, given the player's extensive experience in upmarket sales. Although TS appears appealing and has potential for improvement, the GTM is entirely unique for enterprise. You need to build reseller network, System integrator partners, high value customizations, etc.

If you decide to embrace the security positioning, you must have a diverse portfolio of products. If you model the org. around Palo Alto et al., you need a huge diversity of products, VPN, hardware, cloud security tools, app security tools, etc., as the ICP (CISO) is trying to optimize their allocated budget. People in enterprise are ok with good enough products as long as they meet compliance standards, fit the budget, and does not disrupt operations.

It could be that they might acquire bunch of companies with this capital.

Re: Tailscale has raised $160M

#287

Earlier quoted context omitted.

> I don't understand why people pretend this is an acceptable solution for professional networking Because it IS acceptable for many cases. Many businesses don't operate in such a way as to have centralised infrastructure solely for providing internal networking, nor would they want to add the additional administrative or unnecessary routing overhead. Even locations that would traditionally be considered highly centr…

Also DERP relays having QOS that isn't controlled by myself and I have to hope to get bandwidth through doesn't exactly make me confident about the solution

Sure, but your data is only getting relayed through DERP servers if it cant otherwise establish a direct p2p connection. This can usually be resolved at either side of the connection - if you know about it (which is what the parent was suggesting could be made more clear).

As for your bandwidth concerns in the case of needing to relay, you can even set up your own relay (https://tailscale.com/kb/1118/custom-derp-servers), which would satisfy your desire to be more centralised (i guess you could force all traffic through it, but cant think why you would want to) while still allowing the flexibility of the overlay that tailscale provides.

Re: Tailscale has raised $160M

#288

Earlier quoted context omitted.

> I don't understand why people pretend this is an acceptable solution for professional networking Because it IS acceptable for many cases. Many businesses don't operate in such a way as to have centralised infrastructure solely for providing internal networking, nor would they want to add the additional administrative or unnecessary routing overhead. Even locations that would traditionally be considered highly centr…

Dynamic IP addresses typically also have a forced disconnect at a regular interval. Not really what I want to host services on.

That seems like even more reason to use an overlay - it abstracts all that instability away and gives you a consistent, secure network regardless of what the underlying IPs are doing. Obviously peers can have static IPs too if you think that makes them more stable to routing changes (it doesn't).

Re: Tailscale has raised $160M

#289

I'm a fan of TS and have been a paying customer for work infra for almost a year now. It really is well put together and easy to use, but I do run up against some issues/complaints when diving deep that I hope they can work out: * The pricing tiers and included features by tier penalizes you in frustrating ways. The base plan is a reasonable $6/user/m, but if you want to use ACLs to control anything in a workable way…

> NAT/STUN world you were trying to avoid The clean way to build this is with firewall configuration, opening ports, and static IPs. NAT/STUN and dynamic IPs are just a hack and I don't understand why people pretend this is an acceptable solution for professional networking. Working around an infrastructure that isn't a natural law but can be changed at our will seems like a big waste of time.

Who said you can't do both? NAT makes things easier and you can still properly configure your firewall to keep track of all the NAT traversal rules

Re: Tailscale has raised $160M

#290
You are still trusting the tailscale coordination server for proper key exchange. Yes, traffic is end-to-end encrypted and the private keys stay on the device but there's no way to verify that tailscale is negotiating keys for the machine you asked for
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