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tailscale-vpn-on-demand

#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

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