Bluetooth Headphones Stop working after reboot or power cycle

I have some Insignia NS-BTHDP blue tooth headphones and whenever I restart my Imac or turn off my headphones they stop working. They still connect and the my Imac acts like it is using them for audio output but no sound ever comes from them. I have to remove the device and re-add it to make them work again.
I have seen other people with this issue but never a solution to it.

Thank you for your reply. Do I use one of those bottled air cans to blow out any dirt? Also I have used two different sets of earphones, one (Sony) has 2 rings and the other (Apple) has 3 rings. Thank you again for your advice.

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Bluetooth Headphones Stop working after reboot or power cycle

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