When the Raspberry Pi has no desktop environment, pairing Bluetooth devices requires the command line. bluetoothctl handles it.

Steps

Enter the bluetoothctl interactive mode:

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sudo bluetoothctl

Enable the agent (used for handling pairing requests):

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agent on
default-agent

Start scanning for nearby Bluetooth devices:

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scan on

Once the target device appears, note its MAC address, then run pair, trust, and connect in order:

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pair xx:xx:xx:xx:xx:xx
trust xx:xx:xx:xx:xx:xx
connect xx:xx:xx:xx:xx:xx

The trust step is important – once added, the device will automatically reconnect on the next boot without manual pairing.