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Preheat oven to 350 degrees.
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Grease and flour a 9x13 baking dish.
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Combine dry ingredients for cake in bowl of stand mixer. Stir slowly to combine dry ingredients with paddle attachment.
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Add eggs, milk, oil, and vanilla and mix well, scraping down sides of bowl as needed.
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Turn mixer to lowest speed and slowly add hot coffee, be careful of splashing.
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Bake cake for 35-40 minutes.
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Let cake cool 10 minutes so it is warm but not hot.
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When cake is warm, use the end of a wooden spoon to poke holes all over.
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Working quickly so pudding does not set up, mix Oreo pudding mix with two cups of milk and pour over cake and into holes.
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Some pudding will set up on top of cake.
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Cover and chill cake in the refrigerator for 1-2 hours.
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Once cake is chilled, prepare whipped cream using a stand mixer and whisk attachment.
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Spread whipped cream over cake and top with crushed Oreos.
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Serve chilled.