Step 1: Arrange racks in lower and upper thirds of oven; preheat to 350°F. Line 2 baking sheets with parchment paper.
Step 2: Whisk flour, ground ginger, baking soda, cinnamon, nutmeg, salt, and pepper in a medium bowl.
Step 3: Using an electric mixer on medium-high speed, beat brown sugar, shortening, and butter in a large bowl, scraping down sides halfway through beating, until light and fluffy, about 3 minutes. Reduce mixer speed to low. Add egg, molasses, grated ginger, and vanilla; beat just to blend.
Step 4: Add flour mixture; beat on low speed just to blend. Mix in crystallized ginger (dough will be very soft and sticky).
Step 5: Place raw sugar in a shallow bowl. Using a tablespoon measure, scoop out dough. Using a second spoon, scoop dough from tablespoon measure into bowl with raw sugar; turn to coat well. Roll into a ball. Transfer to prepared baking sheet. Repeat with half of remaining dough and sugar, spacing balls 1 1/2" apart.
Step 6: Bake cookies, rotating sheets halfway through, until edges are firm and centers appear cracked, 10–12 minutes.
Step 7: Transfer cookies to wire racks and let cool.
Step 8: Repeat with remaining dough and sugar, using cooled baking sheets and new parchment.
Step 9: Store airtight at room temperature between sheets of parchment or waxed paper.
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