Yes, it works with speaker or headphones.
It sounds like you’re trying to sideload the wrong file? Are you uploading the zip or the extracted pdx?
Thanks! I am trying to upload the zip of the demo. When I unpack it there is nothing that's able to be uploaded to the playdate. No extracted pdx.
I just figured it out, unpacked it, and needed to move the contents of the source folder up to the top level and then create a .pdx.zip file of that whole thing again. The source folder is one layer too many.