Squats and bending forward creates a stronger retraction of the penis.  That’s probably when your head is slipping back inside the sleeve.  It looks like you may need a smaller silicone ring during those activities.  I ended up getting a custom order with a size 22 ring and a size 30 sleeve.
I think you should definitely send a message to customer support and get Bruce’s opinion.  He has been very helpful for me.  I bet he could give you a good idea of how many sizes to change the ring based upon your pic.
Hope that helps!
