I also notice there is a bug in the Enhanced Usability for Discussion Checkpoints
The settings (gear icon in SpeedGrader) which allows you to set the viewing defaults, With/without context, doesn't actually work. It always defaults to "without context" regardless of the setting. You can change it, save it, and it looks like it saved, but it makes no impact on the Speedgrader window. Clicking the link to show the in context view loads the contextual view for the current student, but should you navigate to a new student, or leave and come back to SpeedGrader, it will default back to the no context view.