You can change the start cutting point of an object using the Change Start button. 

There are a number of reason to change the cut start. If you are having difficulties cutting a complex design and the blades are breaking or it is skipping steps, it may help to start the cut in a different place, such as in a corner rather than in the middle of two arcs. 

You may also want to do this if you are having problems with fallouts sliding behind the mat you are cutting. Changing Cut Order and Changing Start Cut Points may resolve some of these issues.

Click on Options > Show Start Points. 

The initial blade plunge and cut direction will be displayed as a triangle arrow.

Select the desired bevel/cartridge type you wish to change the initial plunge for from the Bevel/Cartridge Type Selection section by clicking the radio button next to it. 

Only the objects matching the bevel/cartridge type selection will be displayed. 

The other bevel/cartridge types of the design on the screen will be muted.

Select the object you want to edit by clicking on it.

Click the Change Start button. This will allow you to change the initial plunge for the object.

Move the blue triangle cursor to where you want the initial blade plunge to start when it cuts this object.

Click the mouse to place the new start point of the initial blade plunge. The start point of this object has now been changed.

Do the same with the other openings, and they will all begin cutting at the bottom corner of the openings instead of at the top.