@crispybacon
Maybe a little bit late, but i had similar pb with pixel 3a and bose speaker.
Thanks to @mateo_salta i solved this by changing some config settings.
Here is a little walkthrough pdf :
https://filedn.eu/lxl4Kp0i9qFSrByo536uLkj/ubports_shared/guide_bt.pdf
you can try it and see if this solves your issue !
If it does, you can revert back the changes once it correctly paired, cheers !