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Step 1
Preheat your oven to 325 degrees. Line a baking dish large enough to fit the ham with parchment paper. (To make cleanup easier.)
Step 2
Slice your ham 1/2 inch thick slices, cutting halfway through.
Step 3
Cut the bottom and top of your pineapple then cut it in half lengthwise. Cut the skin off one half then cut it in half lengthwise again. Cut the tough core out of the two quarters then lay them flat and slice them into thin (1/8 inch thick) strips. Tuck these strips into the cuts you made in the ham, 2 pineapple slices per cut.
Step 4
In a small bowl, mix the honey, balsamic vinegar, and cayenne. Brush a small amount over the ham.
Step 5
Bake the ham 1 1/2 hours then remove it from the oven. Pour the remaining glaze over the top, making sure it seeps into the pineapple filled cuts. Return the ham to the oven for another half hour. Let the ham rest on your counter for 15 minutes before serving.