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1
In a large bowl, cream together butter and sugar.
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2
Beat in egg and vanilla.
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3
Mix in flour and salt.
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4
Remove half the dough, wrap in plastic or wax paper.
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5
Place in refrigerator to chill.
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6
Mix cocoa and peppermint extract into the remaining dough.
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7
Wrap in plastic or wax paper.
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8
Place in refrigerator to chill with vanilla dough for 1 hour.
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9
On a lightly floured piece of wax paper, roll vanilla dough into a 13x9 inch rectangle about 3/16 inch thick.
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10
Carefully lift the wax paper and put it on a cookie sheet.
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11
Chill in the freezer or fridge for a few minutes.
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12
Meanwhile, on a lightly floured piece of wax paper roll out the chocolate dough into a 13x8 inch rectangle about 3/16 inch thick.
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13
Chill for a couple minutes if necessary.
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14
Place vanilla dough on the counter, carefully flip over the chocolate dough and lay it flat on top of the vanilla dough, leaving about 1/4 inch gap on the right side.
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15
Peel the wax paper off the chocolate dough.
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16
Trim edges so that they are smooth and even on all sides.
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17
Starting from the right side, carefully roll up the dough.
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18
If it starts to crack, unroll and let warm up for a minute, then continue rolling up tightly into a long roll/log.
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19
Wrap in plastic or wax paper and refrigerate for 8 hours.
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20
Preheat oven to 400 degrees (F).
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21
Cut roll into slices about 1/8 inch thick and place each slice on a parchment/silpat lined cookie sheet about 1 inch apart.
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22
Bake for 6-8 minutes or until they start to brown around the edges.
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23
Immediately remove from pan and place on cooling rack.
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24
While the cookies are cooling, make the filling: Melt shortening and chocolate in a small pan over medium-low heat.
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25
Add in milk, sugar and salt.
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26
Heat to a rolling boil, stirring occasionally.
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27
Boil 1 minute without stirring.
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28
Place pan in a bowl of ice water and beat until frosting is thick.
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29
Stir in peppermint extract.
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30
Spread frosting on the inside of a cookie and press another cookie on top to make a sandwich.