I never know how to answer those "how strict" hand luggage question. Apart from some low cost airlines like FR which systematically check things (and even then not always), the others have clear rules but whether anyone checks seems to depend on how busy the flight is, which individual person is in charge of the boarding process and ultimately how lucky you are.

If anything, it seems that the bigger the plane, the less they check too so I would guess your PHL flight would most likely be ok while your connection might not be.