Make the cookies: Whisk together the flour, salt and cocoa powder. In a separate bowl, beat the butter, sugar and vanilla until fluffy. Beat in the egg yolks until well combined. Beat in the flour mixture. Form the dough into 2 disks, wrap tightly and chill in the refrigerator for at least one hour.
Preheat oven to 350 degrees. Allow chilled dough to sit out at room temperature for 10-15 minutes, then roll it out onto a floured surface until 1/4 thick. Using a round cookie or biscuit cutter, cut circles in the dough and place onto a parchment-lined baking sheet. Bake 13-15 minutes.
Make the ice cream: Allow ice cream to sit at room temperature for 10 minutes. Dump the ice cream into a large bowl and let it soften another 10 minutes. Mix the raspberries into the softened ice cream with a flexible spatula, smashing some of the berries and leaving some larger pieces. Cover and re-freeze.
Make the chocolate shell: Place chocolate chips and coconut oil into a microwave safe bowl. Microwave on high power for 15 seconds, then stir well. Microwave in 15 second intervals, stirring well between each interval, until smooth.
To assemble the sandwiches, place a rounded scoop of ice cream onto one cookie and place another cookie on top, gently pressing down. Dip ice cream sandwich into the chocolate shell or drizzle on top. Place ice cream sandwiches on a baking sheet and place back in the freezer for 5 more minutes. Serve or wrap individually for storage.