I am still not able to pair my subwoofer (Roku Bass Pro). I actually tried with a newer Roku Streambar Pro (9101R2) and the result is the same. The Streambar Pro is also on the same software 14.0.4. This replacement Streambar Pro bought a new device and was setup from the factory default. The results are the same when I try to pair the subwoofer. It searches, it finds it, then it gets stuck on Updating Subwoofer. The spinning circle never shows any % completed and it errors out after about 5 minutes and says unable to pair. This has now been an issue for more than 2 months and Roku doesn't seem to want to fix it. I've seen other reports of this issue also with the Streambar 9102 model running the same software and unable to pair the wireless speakers, so there is a trend of Roku breaking the wireless accessories with a software update.
Please fix this and release an update.