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 I currently have a Connect (Gen 2) connecting a pair of 25-year old Bose ceiling speakers. The Bose subwoofer is broken. Can I just buy a Sonos subwoofer and be good to go?  If not, and I buy Sonos ceiling speakers, can I use my Connect (Gen 2) or do I need to upgrade that to an Amp? 

Sonos Sub is not designed for use with the Connect, Port, Move, or Roam.

If you want to power a pair of passive in-ceiling speakers, you need either a Connect:Amp or Amp.