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Add all jam ingredients to saucepan and bring to boil.
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Reduce heat to medium and simmer 9–10 minutes until thickened.
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While still warm, transfer jam to tall container and blend with hand blender until smooth.
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Let it cool, then refrigerate until fully set. The jam will thicken as it cools.
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Preheat the oven to 320 degrees F. Line baking sheet with silicone mat or parchment paper.
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In large bowl, combine the dry ingredients.
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Add the wet ingredients and mix with spatula, pressing mixture to absorb liquid into dry ingredients. Then knead by hand until dough comes together.
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Place dough on sheet of parchment paper. Cover with plastic wrap and roll out to 1/4-in. thickness.
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Transfer rolled-out dough onto baking sheet or cutting board and chill in freezer for 2–3 minutes.
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Cut out flower shapes using a 2-in. flower-shaped cookie cutter. If dough cracks when cutting, let it sit at room temperature to soften slightly. Re-roll scraps and continue cutting until all dough is used. For every pair of cookies, cut out one smaller “window” in one cookie to create top layer.
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Bake for 15–18 minutes until slightly golden. Let them cool completely.
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Spread cranberry jam onto back of cookie. Place a windowed cookie on top, pressing gently so the jam fills center. Refrigerate cookies for at least one hour to allow flavors to meld.