How could the Q&A engineers at Apple have missed something so damn obvious?
The iPad in the case sits far enough down on the keyboard dock connector that the iPad is supported, but it’s not far enough down to make contact with the keyboard and allow a sync!
The solution? Either make the iPad dock connectors about 1/2″ higher or cut a slight groove on the base of the iPad dock so that the case of the iPad would “fall” into that groove.
As is, you have to take the iPad out of the Apple iPad case to use Apple’s iPad keyboard dock.
For a massively successful company, they sure make a lot of bonehead design mistakes like this.