You know, I didn't even notice the new headphone jack design, but that's very clever. The iPad 2 is a very thin device; it's frankly amazing how they fit everything into this case. It might not be the most technically powerful device on the market but it's the feel of the device, not the specs, that are impressive. There is a bit of the headphone plug exposed when you have some plugged in, but touching it doesn't produce any sound issues, so I imagine this is a nonissue.