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Roku and Bluetooth Headset Connection

I have several Roku products; two are the streaming stick+ 4k (2017 version) and streaming stick portable 4k (2021 version). So, neither do private listening directly. However, from what I've read both allow for private listening through the Roku phone app. On the portable 4k (2021), I've gotten it to play TV sound through my headphones just once and has yet to do it again. The stick+ 4k (2017) connects and plays every time. I have no clue why one works and the other doesn't. Both are on the same network and band, same headphones (connected, yes) and I do switch between the two in the iPhone app to ensure I'm connected to the right streaming stick when trying to connect. I've even gone as far as banning the stick+ 4k (2017) from my router just to ensure that isn't the issue. Any suggestions would be great.

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