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My Bose headphones can be connected to two devices simultaneously, and paired to more devices (I don't know the limitation for pairing). Same for my 40$ bluetooth speaker.

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Do your Bose headphones randomly cut off in an not so crowded office? Then when your laptop can't see them, does it start playing music over the speakers quite embarrassingly?

Not sure why this is downvoted.

This happens to me, but usually with my phone on the train; happened this morning, in fact.

But it's also happened with other brands so it's not limited to Bose.

Which would mean it's a Bluetooth issue.

I have been exclusively been using bluetooth headphones for over 6 years in a city. I have never experienced any of those issues. I ride the bus and live in have a high population density neighborhood. I work in a building with over 300 workers and haven't had a single incident like that.

Any particular vendor?

LG Neck Bands and GoNovate

GoNovate G10 is the smallest bluetooth that sits in your ear like a hearing aid. I LOVE IT.

For me, it depends on the app that's playing the sound. Some music/video apps automatically pause when bluetooth drops, while others fall back to the device speaker and keep playing.

Same with my $17 bluetooth ear piece, gonovate G10. These things are down right stealthy.

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