To make the Chocolate Cupcakes: Preheat the oven to 350 degrees F. Line 2 (12-cup) cupcake pans with 14 cupcake liners.
In a large bowl, whisk together flour, sugar, cocoa, baking soda, and salt. In a separate bowl, whisk together coffee, oil, vinegar, and vanilla. Pour the wet mixture into the dry mixture and whisk until just combined. Do not over mix.
Fill the cupcake liners about two-thirds full with batter. Bake for 16 to 18 minutes, or until a toothpick inserted in the center of the cupcake comes out clean with a few crumbs clinging to it. Cool the cupcakes completely before frosting.
To make the Frosting: Using a handheld or stand mixer, beat the shortening until smooth. With the mixer running on low, add powdered sugar, vanilla, and 1 tablespoon nondairy milk at a time, as needed, until frosting reaches a spreadable consistency. You may not need to use all of the nondairy milk. Beat on high for 2 more minutes until light and fluffy.
To assemble the cupcakes: Once the cupcakes are completely cooled, slice off the top 1/3 of each cupcake and slather with frosting and sliced strawberries. Place the top of the cupcake back on top and add an additional bit of frosting and sliced strawberries. Dust with powdered sugar.