# Could you please install Tailscale on this computer? ## Retrieval Notes - Session id: `019dca68-5c27-7730-bb7a-c190a9dd4bb9` - Source: `Codex raw session` - Last activity: `2026-04-26T15:33:37.950Z` - Model: `gpt-5.5` - CWD: `/Users/nickyoung` ## My Notes <!-- Add your notes here. This section is preserved across syncs. --> ## Conversation ### User Could you please install Tailscale on this computer? ### Assistant I’ll first check whether Tailscale or Homebrew is already present, then I’ll install the macOS app using the least fussy path available. ### Assistant Tailscale’s CLI is not currently on the path, and Homebrew is available at `/opt/homebrew/bin/brew`. I’m going to use the official Homebrew cask route now. ### Assistant Homebrew needed elevated access for its managed directories, and that approval went through. It’s updating itself and pulling the pieces it needs before installing Tailscale. ### Assistant The app package downloaded cleanly, but macOS stopped the installer at the administrator-password step. I’m going to switch to a macOS-native admin prompt so you can approve it securely in the system dialog instead of typing a password into chat. ### Assistant That macOS admin wrapper can’t be used around Homebrew itself, because Homebrew refuses to run as root. I’m adjusting the route: fetch the Tailscale package as your user, then run only Apple’s package installer with admin privileges. ### Assistant The Tailscale `.pkg` is already sitting in the Homebrew cache, so we don’t need another download. I’m asking macOS to install that package directly now; you should see the normal administrator approval prompt. ### Assistant It looks like macOS is waiting on the admin prompt. Once that’s approved, I’ll verify that the app and CLI are present and launch Tailscale if needed. ### Assistant The app is installed in `/Applications`, and the CLI exists at `/usr/local/bin/tailscale`. The CLI can’t read its preferences until the app has had its first launch, so I’m opening Tailscale once to let macOS initialize it. ### Assistant Installed Tailscale successfully. Details: - App: `/Applications/Tailscale.app` - Version: `1.96.5` - CLI shim: `/usr/local/bin/tailscale` - I opened the app after install. One remaining setup bit: macOS/System Settings is open for Tailscale’s first-run approval. If it asks to allow the VPN/system extension or sign in, approve that there. The CLI currently says `Failed to load preferences`, which usually clears once the app finishes its first-run setup. *La rete privata sarà pronta quando macOS avrà autorizzato Tailscale e l’account sarà collegato.* ### User # Files mentioned by the user: ## Screenshot 2026-04-26 at 17.33.27.png: /Users/nickyoung/Screenshots/Screenshot 2026-04-26 at 17.33.27.png ## My request for Codex: this thing? ### Assistant Yes, that’s the right one. Click `Allow`. That lets Tailscale add its VPN configuration to macOS so it can actually route traffic for the private network. After that, Tailscale may ask you to sign in. *Senza questa autorizzazione, Tailscale è installato ma non può creare la connessione VPN.*