I'm have trouble trying to connect my Sena 20S head piece to the boom box on my new 2023 Ultra Limited. Anyone have any luck with this?

 

Do you have a WHIM?

 

No.
Just bought the bike two weeks ago. no one in sales told me that I needed anyhting to hook up to my existing Sena device,

 

Wireless Headset Interface Module (WHIM)

 

Great, another cost ....

 

Welcome to Harley!

If you had a harley branded Sena headset, you would not need the WHIM.
Here's one for saleFOR SALE Harley-Davidson Sena 50S Bluetooth Headset - Harley Davidson Forums

 

I could be wrong but I believe HD has "walked away" from the WHIM & Sena and no longer support it.

Regardless of Sena branded or HD branded Sena, the WHIM would still be required to make the wireless connection.
The WHIM is out of stock at HD. One would have to find a used one if this is the route one wanted to go.
The only advantage of the HD branded Sena is/was that it gave stereo sound. Sena branded only mono.

 

Thanks