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Preheat oven to 375.
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In a large bowl, beat together shortening, peanut butter, egg, sugar, brown sugar, vanilla, and milk.
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In a medium bowl, whisk together flour, baking soda, and salt.
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Gradually add dry mixture to wet mixture and beat until blended.
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Form into 1" balls.
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Roll in sugar and place a couple of inches apart on ungreased cookie sheet.
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Bake 10-12 minutes or until golden.
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Immediately, gently press an upside down frozen peanut butter cup on top of each cookie and move to wire rack to cool.
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After placing and moving all of the cookies on the wire rack, put in place the candy eyes while chocolate is still slightly soft.
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Place in refrigerator for 10 minutes to allow cookies to firm.
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Put chocolate chips in the corner of zippered sandwich bag.
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Microwave for 20 seconds, knead and repeat until chocolate has melted.
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Clip tiny piece off of the corner of bag to allow for piping and draw eight legs on each spider cookie.
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Place in refrigerator for 10 minutes to allow legs to set.