A:Answer Hello Kyle, yes, the Wonderboom 2 is cross compatible and will be able to pair up with a first gen Wonderboom. Just a reminder, the wonderboom series is only able to pair up with one extra speaker, for a total of 2. When pairing two Wonderboom 2's, you will get 2.1 stereo sound. But when pairing a Wonderboom 2 and a first gen Wonderboom, you'll get mono sound. Hope this helps, have a great day.