Why is my Tailscale and SSH not working?

Troubleshooting
1

So i have following scenario.

Have set up my dietpi. It runs perfectly.

I would want to also remotely (from other wifis annd mobile LTE) access my dietpi.

For example to SSH into dietpi and install software/update etc.

Or access my jellyfin server and stream my home media library.

Using Wireguard works perfectly.

But I thought I could use Tailscale to get the same result without the ddns setup and the router config. (And Tailscale works good on fire tv/android tv devices)

So installation of Tailscale on dietpi works and installed it also on my iPhone +fire tv.

I see all machines in Tailscale admin console and that the vpn connection builds up.

But I cannot ssh into my dietpi.

I thought Tailscale is a zero config VPN.

What am I doing wrong?

2

which IP you used to connect to DietPi? The local network IP or the one Tailscale generated?

1 Like
3

Ahhh… I used the dietpi IP as I would use when I used the Wireguard vpn

When I use the Tailscale ip of the dietpi than it’s working…

But then I do not understand the VPN part of Tailscale.

I thought I would get the IP address of my home network.

That’s why with Wireguard I can access all my services as I would be at home.

But for example if I want to access sonarr, I need to use now two IPs . One when I’m home and another when using Tailscale.

That sounds for me for more work not less work.

Also I want to use a service which is bind to my home IP address remotely (o get banned if I use the services from another IP address.

It seems than this would not be possible because I still see not my home ip address when checking on whatismyipaddress.org

Even though I have turned on Tailscale

Or another use case: how do I hide my traffic in a hotel wifi with Tailscale?

4

I guess there is a misunderstanding what Tailscale is and how it is working. It is not something you can compare with Wireguard 1:1 as it has a different concept. Better you check Tailscale docs to get more inside. To allow sub net routing, some additional steps are needed Subnet routers and traffic relay nodes · Tailscale

1 Like
5

Thanks. I will read the docs