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For the cups:
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Preheat the oven to 350 degrees F.
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If using cooking spray, spray a 24-cup non-stick mini muffin pan with cooking spray. If using vegetable oil, brush both sides of each wonton wrapper with a thin layer of vegetable oil using a pastry brush.
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Push each wonton wrapper into a well of the mini muffin pan.
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Bake for 10-12 minutes until golden. Remove from the oven and increase the heat to 400 degrees F for the shrimp later on.
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Remove the baked wonton cups to a wire rack to cool completely.
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For the guacamole:
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Halve the avocados and remove their pits. Scoop out the flesh and discard the skins. Roughly chop the avocado into cubes (you should have about 1 1/4 cups of cubed avocado).
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Add the avocado to a wide, shallow bowl. Use a fork to mash as smooth as you like it.
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Stir the lime and hot sauce into the mashed avocado.
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Finely chop the cherry tomatoes and add the avocado along with the cilantro and scallion. Gently fold together until combined. Season with salt to taste (usually just a pinch).
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For the shrimp:
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Combine the shrimp, olive oil, garlic and Cajun seasoning in a medium bowl along with a pinch each of salt and black pepper. Stir to coat the shrimp.
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Tip the contents of the bowl out onto a rimmed baking sheet. Bake for 6-7 minutes (the oven should be at 400 degrees F from earlier) until pink and cooked throughout.
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Assemble:
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Fill each baked wonton cup with a slightly heaped teaspoonful of guacamole. Top each one with a shrimp. Sprinkle with the chopped cilantro.
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Serve immediately - the wontons will start to become soft very quickly once filled.
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NOTE:
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If you need to make these ahead - prep the wonton wrappers and shrimp in advance. You can keep the baked wontons in an airtight container at room temperature for up to 2 days. You can keep the cooked shrimp in an airtight container in the fridge for up to 1 day. Make the guacamole just before filling and serving otherwise it will start to oxidize, turning brown.