This may very well be the system in use.

I've seen this effect in several places, not just my work.

Of note: I do not work in the tech sphere. I suspect that this particular loophole may be used by IT personnel to be able to tell the management "yes, we block VPN use" while letting them continue to use their own VPNs. I see no reason to complain.

Initiate while on mobile connection or tethered to one (or just leave it connected from home), use while on that WiFi.

EDIT: I figured this out because I brought my laptop from home to do a few things while at work that needed it. I noticed that my Tailscale connection (initially established at home) was working just fine. That's when I realized that it was the initial authentication that was blocked, not the service.

My phone is usually on my tailnet and my iPad is always on it (and using my home exit node), as a result. Using the exit node has a modest but noticeable effect on battery life, but just being connected is maybe 2% of battery a day. Negligible.

I think this is mostly a Wireguard thing and not specifically a Tailscale thing. Wireguard does what they call "cryptokey routing" where if you prove you possess a key that the other peer knows, you get the traffic (subject to firewall, allowed IPs list, etc etc). Wireguard stores the most recent address:port that it heard from a particular cryptokey on, but it natively lets peers roam, as long as only one roams at a time.

When I work at the local coffee shop I cannot SSH to my remote servers for work on their wifi, but if I connect to Tailscale and use my exit node at home I can. Lifesaver

A TCP over websockets VPN would be fairly simple to write, or ask an AI to write for you

I feel like articles like this do Tailscale a disservice to a certain degree. Most people know Tailscale helps with managing the mesh of connected devices. And as many people have said here you can do this manually with Wireguard, Netbird, Nebula, ZeroTier and many others. Why Tailscale is so helpful is the ACL system. I have about 40 devices connected to my Tailnet and depending on tags devices can or can't access direct communication and also certain exit node networks. Traditional VPNs generally suck because you dump out of a host and have flat access to everything. Tailscale allows you to segment access without disrupting general Internet access with minimal friction and ACLs allow segmentation to happen at the user / device level. Most people aren't using Tailscale ACLs, in fact I rarely hear it discussed. Also the article fails to mention Tailscale Peer Relays [0] which decreases the dependency on DERP relays significantly and are controlled by, you guessed it, ACLs.

[0] https://tailscale.com/blog/peer-relays-beta

I have a phone and laptop; those are my only two "mobile" devices that I might ever use to access my home network remotely. I set them up once, it took a few minutes, and I won't have to do it again unless I replace one of them.

I can completely understand using Tailscale for enterprise networks, but it seems very overengineered for my personal VPN needs.

Update your DNS when it changes. Pretty trivial.

There is a well documented opensource alternative to Tailscale - Headscale. The tailscale client is already opensource, Headscale is opensource drop in replacement for the control server which isn't, and fully compatible with Tailscale clients:

https://github.com/juanfont/headscale

If you can be bothered running the headscale container, you generally don't need to pay for tailscale. It's been pretty well supported and widely used for a number of years at this point. Tailscale even permit their own engineers to contribute to headscale, as the company sees it as complimentary to the commercial offering.

The Tailscale client (non-GUI) is open source: https://github.com/tailscale/tailscale

And they collaborate with Headscale to provide an open-source coordination server (with, unsurprisingly, a more limited featureset, but it works fine with their closed-source GUI client): https://tailscale.com/opensource#encouraging-headscale

I use the combination myself and it works quite well, but of course is less convenient than using their product (which I also do in a different context). Overall I'm pretty happy with their open-source stance.

Whether or not you're being overly paranoid depends on your needs.

As I said on another comment, my use can be tracked by volume and timing, but since I'm only connecting to my house or my in-laws', and using an exit node on one of them, I'm not doing anything with it that I wouldn't do openly from my house. If I were hosting Anna's Archive, it would not do.

As noted by others, Headscale works if you want fully self-hosted. The features it doesn't have aren't important to the typical home user. The free tier of Tailscale is really, really easy to set up and a very non-technical user can just use it if someone with even modest skills, like me, sets it up. That's why I use it. I can talk my wife through how to use Tailscale over the phone. I can set up OpenVPN or Wireguard (I set up an OpenBSD firewall and NAT system in the mid-late 1990s for an office and used it with SSH tunnels and VNC to do some remote troubleshooting), but I can't troubleshoot it remotely with a nontechnical user.

> I don't see mention of open source alternatives

Check out Nebula (created by Slack) - https://github.com/slackhq/nebula

Fundamentally very similar to Tailscale. I've been using it for years and it has been flawless. It doesn't have as many bells and whistles as Tailscale but it does what it does very well.