One way I love to use a cut file, that is intended to be backfilled, is to change the outside cut line to a sketch pen line – this means that the design remains attached to the surrounding cardstock.
To do this I use the Release the Compound Path function which can be found under the Object menu.
I then grouped everything but the outer line and changed the outer line colour to blue.
If you have a Silhouette 3 you can set the line colour to blue for sketch pen and red for cut.
If you have a 1 or 2 you will have to remove the blue line to cut and remove the red lines to sketch.