Add the frozen strawberries, almond milk, sweetener, and vanilla extract to a blender.
Blend until completely smooth and creamy.
Sprinkle a small amount of crushed graham crackers into the bottom of each popsicle mold.
Pour the strawberry mixture evenly into the molds.
Top each mold with additional graham cracker crumbs.
Insert popsicle sticks according to your mold instructions.
Freeze for at least 4–6 hours or until completely firm.
To release the Strawberry Shortcake Pops, run the molds briefly under warm water and gently pull out the pops.