I actually think Tailscale may be an even bigger deal here than sysadmin help from Claude Code at al.
The biggest reason I had not to run a home server was security: I'm worried that I might fall behind on updates and end up compromised.
Tailscale dramatically reduces this risk, because I can so easily configure it so my own devices can talk to my home server from anywhere in the world without the risk of exposing any ports on it directly to the internet.
Being able to hit my home server directly from my iPhone via a tailnet no matter where in the world my iPhone might be is really cool.
You have also added attack surface: Tailscale client, coordination plane, DERP relays. If your threat model includes "OpenSSH might have an RCE" then "Tailscale might have an RCE" belongs there too.
WireGuard gives you the same "no exposed ports except VPN" model without the third-party dependency.
The tradeoff is convenience, not security.
BTW, why are people acting like accessing a server from a phone is a 2025 innovation?
SSH clients on Android/iOS have existed for 15 years. Termux, Prompt, Blink, JuiceSSH, pick one. Port N, key auth, done. You can run Mosh if you want session persistence across network changes. The "unlock" here is NAT traversal with a nice UI, not a new capability.
nothing 100% fixes zero days either, you are just adding layers that all have to fail at the same time
> You have also added attack surface: Tailscale client, coordination plane, DERP relays. If your threat model includes "OpenSSH might have an RCE" then "Tailscale might have an RCE" belongs there too.
you still have to have a vulnerable service after that. in your scenario you'd need an exploitable attack on wireguard or one of tailscale's modifications to it and an exploitable service on your network
that's extra difficulty not less
The difference: Tailscale adds attack vectors that do not exist with self-hosted WireGuard: account compromise, coordination plane, client supply chain, other devices on your tailnet. Those are not layers to bypass, they are additional entry points.
Regardless, it is still for convenience, not security.