The Strap 2.0 can be worn however is most comfortable for you, as long as you wear it the same way every time!  This is especially important for recording workouts.

There are two styles of pegs in the Strap 2.0:

Version 1: smaller bulb part, pops back in to the strap
Version 2: thicker bulb part, screws back together

If Version 1 pops out, here is what to do: 

If Version 2 becomes undone, simply screw the peg back together.