@312Sassy
One of the previous Roku OS updates disabled the ability for multiple users to listen via Private Listening. Likely for perceived security/isolation so not sure if it will be enabled again.
You can look into purchasing an additional bluetooth audio transmitter. These connect to the TV and then multiple headphones/earbuds. etc pair to the transmitter via Bluetooth.
Here is an example link to Avantree.
https://avantree.com/blog/hearing-audio-through-tv-speaker-and-headphones-at-the-same-time.html
https://www.amazon.com/stores/Avantree/page/86FB8A72-4042-4B0C-838B-90525A4C777E?ref_=ast_bln
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There are a few different manufacturers for the above transmitters. I just remember Avantree being compatible for users with hearing aids. At least a good starting point for you to research if fits your needs.
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