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david agerdavid ager 

When I work a Trailhead Challenge, if I create a new Trailhead Playground, the work isn't recognized. I have to do it in my default DE org.

hemanth ramakahemanth ramaka
Can you please clarify on it 
Do you have 2 separate accounts playground and DE or you use the same developer edition for both ??

You can add something go users and check which account is associated with playground
Make sure you are creating playground in that account only