Good afternoon,
Will the 2020 Roku Ultra allow two sets of Bluetooth headphones to be connected at the same time? If not, is there a workaround? Thank you
The ultra won't even work with one bluetooth headphones. The 2020 ultra is bluetooth receiver only, it will not transmit bluetooth to a headphones or speaker. Just receive music from cellphones or tablets. Sorry.
Here is a Roku tech letter released in their community, showing that soon there will be several units that can transmit to headphones etc. One may need to sign into the community to read it. https://support.roku.com/article/228844467
You might not want this because I paired my earbuds to a Roku Streambar and they are incredibly LOUD. Even with the volume turned down to 1 from the new setup, this feature does not work properly.