AirPod Pro bug?
https://support.apple.com/en-us/HT209581
Is this something I have to do constantly? I have had to do this 2-3 times now. Is this a bug?
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Try the following. If this fails, it may be an issue that you should speak to Apple about.
Try a full re-pair, reset, and try again.
Start with Unpairing/"Forgetting" the Device:
Settings > Bluetooth > Airpods > Forget this device. Confirm it.
Put both Airpods in their case, charge them via Lightning for a few minutes (or preferably until the case is 100%). Unplug them. Open the case and hold the button on the back of the case for 15+ seconds or until the light flashes white. Hold them near your iPhone and see if the pairing screen comes up and pair them. If not, repeat until it does. But if you can't see the screen pop up, then manually pair within Bluetooth.
If it doesn't work, open a case with Apple Support here: https://support.apple.com/airpods
Also please let me know the Firmware Version if it doesn't work:
Settings > General > About > AirPods > Firmware Version