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You can absolutely make a headless Raspberry Pi OS Bookworm (Lite or Desktop) auto‑login and automatically start Raspberry Pi Connect, but the trick is understanding what “start Connect” actually means.

Raspberry Pi Connect is a background service (rpi-connect), not an app you “launch.”
If the service is enabled and your Pi is linked to your Connect account, it will automatically register itself with connect.raspberrypi.com on boot.

So the real steps are:

✅ 1. Enable Auto‑Login (Bookworm)

Bookworm uses systemd for login management.

For Raspberry Pi OS Lite (console only)

Enable auto‑login to the console:

sudo raspi-config

Then:

1 System Options
  S5 Boot / Auto Login
    B2 Console Autologin

This sets /etc/systemd/system/getty@tty1.service.d/autologin.conf.

For Raspberry Pi OS Desktop

Use:

sudo raspi-config

Then:

1 System Options
  S5 Boot / Auto Login
    B4 Desktop Autologin

✅ 2. Ensure Raspberry Pi Connect Starts Automatically

Connect is already configured to auto‑start on Bookworm.
Verify:

systemctl status rpi-connect

If it’s not enabled:

sudo systemctl enable --now rpi-connect

This ensures Connect starts at boot and stays running.

✅ 3. Make Sure Your Pi Is Linked to Your Connect Account

Connect will not appear online until the Pi is linked.

Run:

rpi-connect link

Follow the pairing code instructions.

Once linked, the Pi will automatically appear at:

https://connect.raspberrypi.com

⚠️ Important Clarification

You do not need to “start” Connect manually after login.
There is no GUI or command to launch.
The service runs in the background and exposes:

  • Remote shell
  • Remote desktop (if using Desktop edition)

If the service is running and the Pi is linked, Connect works.

🔧 Optional: Force Connect to Start After Network Is Up

If your Pi boots faster than your network, add a dependency:

sudo systemctl edit rpi-connect

Add:

[Unit]
After=network-online.target
Wants=network-online.target

Save and reload:

sudo systemctl daemon-reload
sudo systemctl restart rpi-connect

🎯 Summary

Task Command / Setting
Auto‑login raspi-config → Boot / Auto Login
Enable Connect service sudo systemctl enable --now rpi-connect
Link device rpi-connect link
Check status systemctl status rpi-connect

Once these are done, your Pi will:

  1. Boot
  2. Auto‑login
  3. Start the Connect service
  4. Appear online at connect.raspberrypi.com