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Ingredients
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Sandwich
Maple aioli
Dredge (optional, for classic deep-fried style)
To finish
Method
Maple aioli
In a small bowl combine mayonnaise, maple syrup, Dijon mustard, lemon juice, and grated garlic. Whisk until smooth. Season with kosher salt and black pepper, taste and adjust maple or lemon as needed. Chill in refrigerator while you assemble sandwiches (at least 10 minutes) to let flavors meld.
Sandwich assembly
Lay out 4 slices of challah. Spread about 1 tablespoon of the maple aioli evenly on each slice. On each of the 4 slices, layer 3 slices of ham (slightly overlapping) and 2 slices of Swiss cheese. Top each sandwich with remaining challah slices, aioli side down, pressing gently to compress.
Butter exterior
Spread about 3/4 tablespoon softened butter evenly on the outside face of each assembled sandwich (top and bottom) so both exterior sides are lightly buttered for browning.
Pan-fry method (recommended: crisp exterior, melty interior)
Heat a large skillet or griddle over medium heat until hot. Add 1/2 tablespoon vegetable oil and swirl. Place one sandwich in skillet and cook 3–4 minutes per side, pressing gently with a spatula, until bread is golden brown and cheese is melted. If bread browns before cheese melts, reduce heat to medium-low and cover pan with a lid for 1–2 minutes to trap heat and finish melting. Repeat with remaining sandwiches, adding oil as needed. Transfer cooked sandwiches to a cutting board and let rest 1 minute before cutting in half diagonally.
Optional dredge & shallow-fry method (for classic Monte Cristo exterior)
If you prefer a battered exterior: whisk eggs, milk, flour and 1/2 tsp salt in a shallow bowl until smooth. Heat a skillet over medium and add enough vegetable oil to coat bottom (about 2–3 tablespoons). One at a time, dip assembled and buttered sandwiches briefly into egg mixture, turning to coat both sides and letting excess drip off. Place sandwich in hot skillet and fry 2–3 minutes per side until golden and crisp and cheese is melted. Drain briefly on a wire rack or paper towel.
To serve
Dust sandwiches lightly with powdered sugar if desired. Serve each sandwich with extra maple syrup and additional maple aioli on the side for dipping. Recommended: cut each sandwich in half on the diagonal and serve immediately while warm.