Sticky Pineapple Brown Sugar Glazed Ham

Lord, this ham. I've been making it for holiday dinners for almost a decade now, and it never fails to make people hover around the kitchen asking when dinner's ready. The sticky-sweet glaze with chunks of pineapple gets all caramelized and candied around the edges of each ham slice. It's honestly ridiculous how something this simple turns into such a showstopper.

I served this at last Easter when my in-laws visited from Michigan. My mother-in-law, who normally picks at her food, had three helpings and then asked me for the recipe while helping with dishes. She whispered that it was better than her sister's ham, which apparently had been the family favorite for 20 years. I consider that the ultimate cooking victory.

Perfect Ingredients

• Pre-sliced boneless ham - Get the spiral-sliced kind if possible. Those little cuts are perfect pockets for the glaze to seep into. I like the quarter ham size (about 2.5 pounds) for a regular family dinner.
• Canned pineapple rings - Make sure you're getting the kind in 100% juice, not syrup. The juice becomes part of your glaze, and the rings look gorgeous arranged between ham slices.
• Dark brown sugar - Don't substitute light brown here. The extra molasses in dark brown gives this a deeper, almost caramel-like flavor that makes all the difference.
• Champagne vinegar - I stumbled on using this instead of regular white vinegar when I was out of the latter one Christmas. The slightly milder, fruitier tang works so well with the pineapple. White wine vinegar works too.
• Coarse ground dijon - Those little mustard seeds pop in your mouth when you bite in. It's one of those little details that makes people wonder what your secret is.

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Cooking Instructions

Prep your ham

Pat your ham slices dry with paper towels (seems fussy but helps the glaze stick). Arrange them in your baking dish, pulling the slices apart a bit so they fan out. Tuck those pineapple rings in between some of the slices. When I'm feeling fancy, I secure them with toothpicks so they don't slide down during baking.

Make that glorious glaze

Pour that reserved pineapple juice into a saucepan and add your brown sugar, vinegar, mustard, molasses, Worcestershire, salt, pepper, allspice, and liquid smoke. When this starts simmering, your kitchen will smell so good you'll want to bottle it as perfume. Let it bubble away for a few minutes until the sugar completely dissolves.

Get it sticky

Mix your cornstarch with cold water in a small cup (I use a fork to avoid lumps). Pour this into your simmering glaze while stirring constantly. The transformation happens fast - suddenly you've got this thick, glossy sauce that coats the back of a spoon. This is what gives you that sticky-tacky texture that clings to the ham.

First bake

Pour half your glaze over the ham, making sure to get it down between those slices. Use a spoon to really work it in there. Cover with foil and bake at 325°F for half an hour. This gentle heat helps the ham warm through without drying out.

Glaze and crisp

Here's where the magic happens. Crank up that oven to 425°F and remove the foil. Brush the remaining glaze all over, getting into every nook and cranny. That higher heat caramelizes the sugars, creating those irresistible sticky, almost-burnt edges that everyone fights over.

Rest and serve

Let it sit for 10 minutes after taking it out of the oven. This isn't just chef-talk - it actually helps the meat stay juicier when you cut into it. Transfer to your prettiest platter and spoon those pan drippings over top. If you're feeling fancy, throw some fresh thyme sprigs around it.

My grandmother used to make a version of this with just brown sugar and mustard. Good, but not great. One Thanksgiving about 15 years ago, I was flipping through her recipe box and found a newspaper clipping with a splash mark on it - clearly one she'd used. It had this pineapple variation with a handwritten note: 'Better than mine!' I've been making it her way - with my few tweaks - ever since. Every time that smell fills my kitchen, I think of her.

Serving Thoughts

Slice this beauty alongside some crispy roasted potatoes that have been tossed with rosemary and garlic. The contrast between the sweet ham and savory potatoes is just perfect. For holidays, I put out little dinner rolls so people can make sliders with the leftovers. And always something green - either roasted brussels sprouts or a simple arugula salad with lemon to cut through the richness.

Mix It Up

For Christmas, I add a splash of bourbon to the glaze and some orange zest. The citrus brightens everything up and the bourbon adds this warm, oaky undertone. If you're feeding spice-lovers, add a minced jalapeño to the glaze - the heat with the sweet is fantastic. For a deeper flavor, substitute maple syrup for half the brown sugar - especially good for a brunch ham.

Keeping It Fresh

Leftover ham makes the best breakfast ever. Store it in a sealed container in the fridge for up to three days. For sandwiches, I like to warm the slices in a skillet rather than the microwave - you get crispy edges that way. If you're freezing leftovers, wrap portions tightly in foil, then in freezer bags with the air pressed out. Future-you will be so grateful on a busy weeknight.

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Cook's Secrets

• If your ham starts getting too dark before it's heated through, lay a piece of foil just over the top bits that are browning too fast
• For extra flavor, stud the ham with whole cloves before glazing - just remember to remove them before serving
• Let the ham sit at room temperature for 30 minutes before baking for more even cooking

I've made this ham for everything from Christmas dinner to random Sunday suppers when I want leftovers for the week ahead. There's something so satisfying about the process - watching that glaze bubble and thicken, smelling the sweet-spicy aroma that fills the kitchen, and seeing people's faces light up when you bring it to the table. It's the kind of recipe that makes you look like you worked way harder than you actually did, which in my book is the very best kind.

Frequently Asked Questions

→ Can I use a spiral cut ham instead?

Yes! Spiral ham works great with this glaze. Just follow the same instructions, making sure to get glaze between all the pre-cut slices.

→ Do I need to use dark brown sugar?

Dark brown sugar gives the best caramel flavor, but light brown sugar will work if that's what you have on hand.

→ Can I make the glaze ahead of time?

Yes, you can prepare the glaze up to 2 days ahead. Store in the refrigerator and warm slightly before using.

→ What sides pair well with this ham?

This ham pairs beautifully with scalloped potatoes, roasted vegetables, dinner rolls, and green bean casserole.

→ Can I use fresh pineapple instead of canned?

While possible, canned pineapple works best because you need the juice for the glaze. If using fresh, you'll need to add pineapple juice separately.