How does tailscale "work"?

I was attracted by the advertising claiming that tailscale require minimal input from users to connect to various devices. But I have just been battling with this for hours and getting nowhere.

I have a simple request, connect to Remote Desktop from various devices. But I simply cannot see how this can be done. I followed the firewall instructions, all the devices had connected to the tailscale app and as soon as I am outside the local area network, nothing can be connected.

I even tried to to enter the gateway information based on the IP numbers and getting nowhere with that.

I also cannot see how you can connect multiple users to a Remote Desktop, seeing that only one account is displayed at any given time for a machine.

I am unhappy because you advertised this to be a simple and easy process, but my experience has been far from enjoyable and nothing has been achieved at all.

Tailscale works quite well for me. I was able to get connected in like 15-20 minutes. I hope that you did test it out before you paid for any sort of subscription?

Not too sure where you got the information that Remote Desktop (I assume Windows RD) can have more than 1 session. Unless you do some (potentially illegal) modification, only one account/user session can be connected at a time.

Which gateway information based on IPs are you talking about?

Tailscale does not work for me.

Remote Desktop can be assessed with multiple users at the same time, each with their own licenses etc… Besides, the software they have access to will be written in house so there isn’t any issues of copyright etc…

There is a gateway on Windows Remote Desktop, which is the first thing I want to try before moving to a more sophisticated remote desktop solution that allows multiple users to logon virtually at the same time. Tailscale failed even on that.

In any case, I have removed and closed my tailscale account. Not interested in spending hours with this.

My guess (since there are no real details on what you actually tried) is that you were trying to access the PC’s via their internal IP address, and not the Tailscale address. For a simple test, you should be trying to RDP to a 100.x.x.x IP address.

If that works, then you can look at things like Subnet routers that will allow you to use the internal IP address (IE: 192.168.x.x or 10.x.x.x, etc).

I think you might be mistaken. With RD gateway is still not allowed to have multiple users at the same time on one device. You will still need to have multiple devices behind that gateway if you want to have different sessions. RD Gateway is for users to connect to their RD via this gateway into their device(s) in their internal network. You sort of need to ‘expose’ this gateway to the public. So you connect to this RD gateway and the gateway then creates a connection to the internal device you want (among other things). You will still need multiple devices if you plan to RD various users in at the same time.

And you probably won’t need the RD gateway if you are using some sort of a VPN like tailscale (you can of course but this becomes less useful). You can install tailscale on each of the internal device you want to RD in and directly connect/RD to it, without the RD gateway. Or as muzicman0 suggest, you can use a subnet router as well.