#post
tailscale vpn on demand
Automatically connect based on network rules.
Using VPN On Demand for iOS and macOS · Tailscale Docs
I did the pictured settings that connects my phone to the tailnet whenever I’m on my home wifi or off wifi.
Still need to do everything here to set up the home network: How to get started with Tailscale in under 10 minutes - YouTube
Having trouble connecting on Mini
Uninstall macOS App Store version
If you downloaded it this way, you’ll find it’s more limited (e.g. no ssh).
The fix is to download from tailscale instead of the app store.
To remove the app store version follow this guide: https://tailscale.com/kb/1069/uninstall?tab=macos+%28app+store%29
Here’s a command to delete the local files you shouldn’t have:
trash "~/Library/Application Scripts/*.io.tailscale.ipn.macos" \
"~/Library/Application Scripts/io.tailscale.ipn.macos" \
"~/Library/Application Scripts/io.tailscale.ipn.macos.login-item-helper" \
"~/Library/Application Scripts/io.tailscale.ipn.macos.share-extension" \
"~/Library/Caches/io.tailscale.ipn.macos" \
"~/Library/Containers/io.tailscale.ipn.macos" \
"~/Library/Containers/io.tailscale.ipn.macos.login-item-helper" \
"~/Library/Containers/io.tailscale.ipn.macos.network-extension" \
"~/Library/Containers/io.tailscale.ipn.macos.share-extension" \
"~/Library/Containers/Tailscale" \
"~/Library/Group Containers/*.io.tailscale.ipn.macos" \
"~/Library/HTTPStorages/io.tailscale.ipn.macos" \
"~/Library/Preferences/io.tailscale.ipn.macos.plist" \
"~/Library/Tailscale"
- A missing step in the guide is to remove Tailscale from “Login items” if you added it there.
- Another is the
/usr/local/bin/tailscale
executable
SSH server installation
If you want to SSH to a Mac, that means you need to choose the third installation option here:
Specifically, you need to install the tailscale
+ tailscaled
CLI tools and no GUI app.
Discussion here about why that installation method is necessary: https://github.com/tailscale/tailscale/issues/4518
Installation instructions here: https://github.com/tailscale/tailscale/wiki/Tailscaled-on-macOS
Video here: What is Tailscale SSH? | Tailscale Explained - YouTube
Ensure you add the Go binaries to your path so the tailscale
command will work:
export PATH="$HOME/go/bin:$PATH"
CLI docs here: https://tailscale.com/kb/1080/cli#ssh
Needed to run this to log in and make mac an SSH server (i.e. a device that can be ssh’d to):
$ tailscale up --ssh
Then ssh to it from other devices like this:
$ tailscale ssh user@device
With Plex
- Installed recommended Mac client on Air
- Installed CLI-only clients on Mini so it could act as an SSH server
- Installed iOS client on phone
- Install tvOS client on Apple TV
- Updated plex network settings to include the IP address of the media server:
Inbox
- Tailscale quickstart · Tailscale Docs
- Install Tailscale on an Apple TV · Tailscale Docs
- Setting up a server on your Tailscale network · Tailscale Docs
- Axiom + Tailscale: elevate your network visibility and security
- Device approval · Tailscale Docs