Remote Setup Guide: Connecting Your ProductiveBot via Tailscale

Tailscale is free and takes about 2 minutes to install:

1. Open the Mac App Store listing for Tailscale
2. Click Get, then Install
3. Sign in with your Apple ID if prompted
4. Once installed, open Tailscale from your Applications folder or Spotlight

That's it — continue with Step 2 below.

This is a known macOS bug. Try these in order:

1. Wait 10 seconds — sometimes it just needs a moment
2. Click somewhere else on the desktop, then click back on the popup
3. Press Esc to dismiss, then run the command again
4. Force-quit Tailscale: press ⌘ Cmd + ⌥ Option + Esc, find Tailscale, click Force Quit — then re-run the command
5. Restart your Mac and try from Step 1

Try opening it from Terminal:

If that doesn't work, kill any stuck processes first:

Still stuck? Restart your Mac and try again.

Something on your Mac may be interfering:

• Screen Time — can block network extensions. Try disabling it temporarily in System Settings → Screen Time.
• Antivirus software — programs like ESET or Norton can interfere. Try temporarily disabling them.

If neither applies, restart your Mac and try again.

• Default password: productivebot
• You won't see any characters while typing — that's normal
• If you've changed your Mac password, use that one instead
• After 3 wrong attempts, wait 30 seconds and try again

Tailscale is already set up. Check the connection:

If you need to reconnect with a new key, log out first:

Then run the setup command from Step 2 again.

Tailscale may not be installed. Contact us and we'll help, or download it yourself:

Download Tailscale from the Mac App Store

After installing, restart your Mac and try the command again.

Most VPNs use aggressive firewall rules that block Tailscale traffic. If you have another VPN running:

• Temporarily disconnect the other VPN while running the setup command
• Once Tailscale is connected, you can usually re-enable your other VPN — Tailscale only uses a small portion of your network traffic and typically coexists fine
• If you still have issues, try adding a split tunnel exception for Tailscale in your VPN's settings

If you have the macOS firewall enabled, it may block incoming Tailscale connections:

1. Open System Settings → Network → Firewall
2. Click Options
3. Make sure "Block all incoming connections" is OFF
4. If Tailscale appears in the list, make sure it's set to Allow

Your setup key is one-time use and expires after 14 days. If you see this error:

• The key may have already been used (keys can only be used once)
• The key may have expired (14-day window)
• Contact us for a fresh key — we'll send one right away

Tailscale is a secure, private network — like a VPN but much simpler. It creates an encrypted connection between your Mac Mini and our support systems. Only authorized ProductiveBot team members can access your machine for setup purposes. No one else can see or connect to it.

We can only access specific services needed for ProductiveBot setup — we can't see your screen, browse your personal files, or access anything beyond what's needed. All traffic is fully encrypted end-to-end. You can disconnect anytime:

Yes — your key is one-time use only and expires after 14 days. Once you've used it to connect, the key is consumed and can't be reused. If you need a new key (for example, if yours expired before you could use it), just contact us and we'll send a fresh one.

Yes. Once we've finished setting up your ProductiveBot, you can ask your bot to disconnect from Tailscale by telling it:

"Please disconnect from Tailscale"

Your ProductiveBot will handle the rest. You can also re-enable it anytime if you need support in the future.

No. Tailscale runs efficiently in the background and only routes ProductiveBot-related traffic. Your normal internet is completely unaffected.

Nope! Once you've run the command, you can close Terminal. Tailscale runs in the background and reconnects automatically — even after restarting your Mac.