I keep it running always. Partly to access stuff at home, and party to get the ad-blocking from pihole.

Do not expose stuff unless you fully understand the security risks

isn’t it an annoyance having to connect to your home network all the time?

It's less annoying than the gnawing fear that my network might be an easy target for attackers.

How annoying is it to connect to VPN/use Tailscale

I think it’s very important to separate a random “VPN” solution to using Tailscale.

instead of being able to access the service directly?

Focusing on Tailscale. Who turns off Tailscale? It is “directly” connecting to your service or app or whatever. That’s the whole point.

For an external VPN like mullvad, I run my own proxy. Again it's only available from my VPN or inside my network.

It uses socks5 and gluetun docket containers and in apps that support proxies, I can add my proxy to it and it'll route that traffic through the paid VPN.

Or, a work profile (see shelter) or androids new private spaces. If you have private spaces, it uses a seperate network. So if you have a VPN installed outside the private space, it won't work on apps inside the space. So, what you could do is have a paid VPN inside private spaces, and use it and a web browser or whatever there, and use your server's VPN outside the private space.

Lmk if you want any of my docker composes

Sucks a high hard one if you plan for others to use your services too. If it's just you it's not that annoying

🤔

I think the part you’re missing (and others haven’t addressed) is that you don’t send 100% of your traffic to one endpoint (much like how most use VPNs). You can route different things to different places.

For example, I’m in the US and have two Tailscale exit nodes. Both are located on VPS machines in the US, but one sends traffic down a double-hop VPN back out into the US, the other does the same but to Switzerland. My “default” route is through Switzerland (better privacy laws) but I am forced to route some things through the US exit node due to websites that won’t work outside the US. For my personal devices, traffic routes directly to them via WireGuard tunnels.

In addition, my wife doesn’t care about blocking everything that I do (social media, tracking) but her phone still needs to update sensors in Home Assistant. She can choose not to use the exit nodes but can still communicate with our nodes on Tailscale. She also uses it to print documents at home from her laptop while she’s at work.

Recently I was waiting in a hospital with public (unsafe) WiFi that blocked UDP traffic, but Tailscale does some magic that will relay traffic via TLS. I was able to access services at home with a 20ms latency. The tech is very, very nice to have.

Use Tailscale, for the most part it's pretty transparent. As long as all the magic DNS stuff is setup correctly, I can access all my internal services by name and it just works.

I can't use VPN on my work PC so I have some services open on sub domains that aren't in my DNS. Follow some basic rules and it's fine. My phone is always connected to my Wireguard running on Opnsense. It's simple, fully self hosted and works great.

Im using tailscale and have all my devices connected through it. Im not exposung any services in particular, just handy to be able to ssh around. Its always on and i did not notice huge power loss on my phone

If you have an iPhone, it’s a pain over Tailscale because Tailscale frequently likes to disconnect for various reasons and this isn’t something Tailscale can fix, it’s something with the way Apple manages background processes.

If you’d like an alternative, you can host your services directly to the internet via a reverse proxy like Caddy or Nginx, and then use mTLS to secure that access with a certificate you load only onto your devices.

Depends on how secure the application and the security you use in front of the application such as reverse proxies, load balancers, etc. If you are exposing a web application with no SSL, no two factor with, or something in a beta state or if you can't trust your ISP not to create man-in-the-middle attacks for advertising and collecting information to sell which also likely introduces security vulnerabilities, then that could be a problem and a VPN or similar might be a big help.

Not much, I have services that run both externally and only over wg.

Only issue with wg is sometimes I have to shut it off for things like multicastdns, or otherwise that try to look around the network or wifi.