Heat oven to 250ºF.
Remove the ham from its packaging, rinse, and drain thoroughly. Place the ham, cut-side down, in a roasting pan lined with a clean kitchen towel. Using a small paring knife or clean utility knife set to the smallest blade setting, score the ham from bottom to top, spiraling clockwise as you cut. (If you're using a paring knife, be careful to only cut through the skin and first few layers of fat.) Rotate the ham after each cut so that the scores are no more than 2 inches apart. Once you've made it all the way around, move the knife to the other hand and repeat, spiraling counter-clockwise. The aim is to create a diamond patternDon't worry too much about precision here. all over the ham.
Remove the towel and tent the ham with heavy duty foil, insert a probe thermometer, and cook until the internal temperature at the deepest part of the meat registers 130ºF, 3 to 4 hours.
Remove the ham from the oven and use tongs to pull away the diamonds of skin and any sheets of fat that come off with them.
Increase the oven to 350ºF.
Pat the ham dry with paper towelsOtherwise, the coating is going to slide right off., then brush on a liberal coat of mustard. Sprinkle on brown sugar, packing loosely as you go until the ham is coated. Spritz this layer lightly with bourbon, then loosely pack on as much of the crushed cookies as you can. You may not use all the mustard, brown sugar, bourbon, or cookies, depending on the size of your ham.
Insert the thermometer (don't use the old hole) and return to the oven, uncovered. Cook until interior temperature reaches 140ºF, about 1 hour.
Let the ham rest for 30 minutes before carving.