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I am eligible to upgrade products my Pay:1 and Play:5 (Gen 1).

If I did this are old ones still usable and able to group with the new products?

I understand they won’t be eligible for a further discount but am just concerned getting use from the speakers and making sure they function.  

The Sonos product upgrade program is briefly outlined here

https://support.sonos.com/s/article/3574


You can still use the old speakers, but note that Play:5 (gen 1) is only compatible with S1 and some newer products only with S2, so they operate under separate systems and cannot be grouped.

https://support.sonos.com/s/article/4786?language=en_US