Crush the freeze-dried strawberries in a ziplock bag using a rolling pin or mallet.

Cut each Medjool date lengthwise using a sharp knife to remove the pit and open for stuffing.

Mix finely shredded coconut, coconut flour, plant-based milk, pure maple syrup, strawberry jelly, and pure vanilla extract until smooth and creamy. Fold in crushed freeze-dried strawberries.

Stuff each date with about one tablespoon of the coconut mixture, packing it in gently.

Place stuffed dates on a parchment-lined baking sheet and freeze for 30 minutes.

Melt dairy-free chocolate chips and coconut oil in a double boiler over low heat, stirring until smooth.

Dip each chilled date into the melted chocolate, allowing excess to drip off, then place back on parchment paper.

Sprinkle crushed freeze-dried strawberries on top before chocolate sets, then refrigerate for 1 hour until hardened.