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Re:How our free plan stays free by xanaxagoras on Wednesday March 16, 2022 @03:38PM (#30703025)
I've wondered this as well. Everyone seems to rave about it, but I run my own wireguard and don't find it too hard to add devices to the network. I think maybe you can use it to expose certain things to the internet easily? I don't have a lot of trouble doing that either. I've scrolled around their marketing site for a few minutes before and I just don't really get what all the fuss is about. I'm sure I'm missing something.

I will say, and I think this is right, the proposition here isn't a VPN like Nord which you'd use to hide your traffic from your ISP or masquerade into a different geolocation, but rather a VPN for connecting to your own devices.

Re:How our free plan stays free by hobofan on Wednesday March 16, 2022 @04:11PM (#30703432)
> I'm sure I'm missing something.

Can you really not see the difference between this[0] and this[1]?

This really feels like a "What's the value in Dropbox when everyone has access to rsync and bash?" situation.

[0]: https://www.wireguard.com/quickstart/

[1]: https://tailscale.com/kb/1017/install/

Re:How our free plan stays free by iso1210 on Thursday March 17, 2022 @08:13AM (#30710262)
I still don't see the value of dropbox, it seems to remove control, suck up resources, and occasionally wipe out files.
Re:How our free plan stays free by xanaxagoras on Wednesday March 16, 2022 @04:21PM (#30703540)
I can see that it's easier to setup for someone who doesn't know how to use WireGuard, but not how it would benefit me personally. I guess SSO is nice.

I think it's more like... "What's the value in Dropbox when I'm already running Nextcloud?"

Re:How our free plan stays free by gowld on Wednesday March 16, 2022 @04:59PM (#30704023)
The value is you can stop running Nextcloud.
Re:How our free plan stays free by tptacek on Wednesday March 16, 2022 @05:39PM (#30704465)
It's very easy to run your own WireGuard, and if that's all you want, by all means, do that. A lot of work went into making WireGuard the easiest-to-configure VPN --- it's deceptively sophisticated (the best kind of sophisticated).

Tailscale is also deceptively powerful, and that's why people love it. In particular: getting WireGuard deployed across a whole team with a single source of authentication truth and role-based default-deny ACLs is not, in fact, very easy to do. The massively more common pattern in tech companies with access VPNs is something like OpenVPN, with separately-managed credential stores (that get desynced and lock people out --- or accidentally retain access for separated team members) and default-allow network policy that gives anyone with access to the VPN direct access to Redis, databases, staging instances, and stuff like that.

I don't just like Tailscale. I fucking hate Tailscale for how simple they've made one of the larger problems in corpsec. It's maddening.

Re:How our free plan stays free by xanaxagoras on Wednesday March 16, 2022 @07:03PM (#30705274)
That's true, the ACLs are pretty huge. I've heard about Tailscale almost exclusively in the context of /r/selfhosted, and this post is about the free plan which guided my response. It's not hard to see why this would be useful at my job. Honestly I wish they'd pay for it, OpenVPN is such a pain for my users.
Re:How our free plan stays free by mikeyschaefer on Wednesday March 16, 2022 @05:12PM (#30704167)
If your ISP does CGNAT a typical WireGuard setup won’t work without a public IP address. Tailscale makes it possible to use a VPN without a public IP. I use Tailscale with Starlink which uses CGNAT.
Re:How our free plan stays free by xanaxagoras on Wednesday March 16, 2022 @07:14PM (#30705394)
Not something I'd have looked for as my ISP does not have that issue, but yeah, that's a killer feature.
Re:How our free plan stays free by TheFlyingFish on Wednesday March 16, 2022 @05:32PM (#30704379)
Tailscale has three main pieces of functionality over vanilla Wireguard: Automatic peer configuration, NAT holepunching, and network ACLs.

I won't talk much about ACLs since if you're the only user on your VPN, they don't matter. E.g. I use Tailscale but I don't use ACLs because who am I going to block from connecting to what? Am I concerned about my server trying to compromise my Raspberry Pi? (Maybe I should be, but life's too short so I don't bother.)

Automatic peer configuration is a pretty killer feature, though. If you're just running plain vanilla Wireguard, then you have to manually copy keys between every pair of devices that need to be able to talk to each other. That's fine if you only have a few devices, or if you have a large number of devices but you're happy to use a hub-and-spoke model where each "client" only talks to the hub, and the hub routes all traffic. But once your number of devices starts to grow, or you decide you want direct links instead of hub-and-spoke, it can start to get unpleasant.

NAT holepunching may seem unnecessary if you're used to having a VPN hub and just port-forwarding to it. But it opens up a whole set of possibilities that would just be non-starters without it. Just off the top of my head, here are some things that I would consider easy with Tailscale but cumbersome-to-impossible without:

1. Not having to worry about static IP assignments on my LAN. Admittedly, this is more of a convenience than a true barrier to anything, but with vanilla wireguard one of the devices needs to be able to initiate the connection, meaning that the other has to be able to receive unsolicted traffic on some port. Normally I'd do that with port forwarding, but all of the port forwarding I've ever done requires a fixed internal IP to which to forward the port. Instead, with Tailscale, you can just plug in your server/RPi/whatever and forget about it.

2. Similarly, you can take advantage of this to get a window into a network that you don't control. (It sounds bad when I put it that way.) Say you've got a relative a long ways away, and they're constantly calling you for help with their network and you're constantly walking them through how to fiddle with their router settings or something - with Tailscale, you could just preconfigure a Raspberry Pi, ship it over, and not have to worry about being able to connect to it once they plug it in. Voila, you have an entrypoint into Grandma's network or whatever.

3. Self-hosting afficionados like myself tend to turn to "can I put a thing on a server somewhere" as a solution to many problems involving cross-device communication: file synchronization is an obvious example. But what if all the devices could seamlessly talk to each other, anywhere and anytime? Then you could pop, say, Syncthing on each device and not have to worry about having a server up.

Tailscale also has some extra goodies like being able to share a device to someone else's Tailnet, so if you run (say) a Plex server and you want to let someone else talk to it without exposing it to the greater internet that's pretty easy.

Their "Magic DNS" feature is also quite convenient - I used to pride myself on being able to remember all the IPs I had assigned to all my network-connected stuff and therefore not needing DNS, but since I've started using Tailscale I've found myself defaulting to DNS names more and more without ever even consciously deciding on it. Words are just more memorable than numbers, there's no need to fight it.

All that said, if none of those use cases seem compelling to you then maybe Tailscale just isn't for you. Different strokes for different folks.

Re:How our free plan stays free by tptacek on Wednesday March 16, 2022 @05:42PM (#30704495)
This is all great stuff, and reasons to respect Tailscale, but honestly the killer feature for their big-money customers, and the reason I have such strong feelings about it, is much simpler: Tailscale does SSO login, and does it extremely well. If you're running a security practice for a growing tech company, one of the most important early jobs you have is getting all your services migrated to SSO. VPNs are notoriously annoying to SSO (I have seen some janky Okta integrations for OpenVPN).
Re:How our free plan stays free by mdeeks on Thursday March 17, 2022 @12:43AM (#30707744)
It’s atrocious. We are using OpenVPN with Okta LDAP and you have to type “password,totpcode” as your password. Alternatively you can type just your password and wait for it to send a push to your phone while OpenVPN is completely blocked waiting. You have a yubikey? That’s a damn shame. Training and support for this for our entire company was a pain in the ass. I also felt embarrassed having my name on rolling out something so janky. We are trialing Tailscale now and onboarding is two minutes and practically doesn’t need a guide (Download the app. Click login. Okta auth however you want). Our OpenVPN guide is like 8 pages.
Re:How our free plan stays free by willstrafach on Wednesday March 16, 2022 @06:01PM (#30704694)
I think the pitch here is “Semi-managed WireGuard peer provisioning and NAT punching as a service” usable by anyone who may not otherwise have a clue how WireGuard works (eg. friends sharing access to a file/media server), within 5 minutes or less from download/login to “done”