The Plantronics Bluetooth stereo headset I have never fails to connect to my devices on startup. It will connect to two or three at first power up, announcing them as it does so. It has the reverse problem, I then want to signal which device should take priority over the limited bandwidth&#x2F;processing on the device for audio quality. But I mention it because not all Bluetooth headphones pair to only one device at a time --though all the rest of mine share that limitation. And if USB-C is also an option, pairing fixes could be as easy as the iPad Pro&#x27;s Pencil pairing: just plug it in and unplug when you want...