Add the room temperature unsalted butter and caster sugar to a bowl and mix until just combined and creamy.
Add the vanilla, plain flour and cocoa powder and start to beat together, adding the milk a little at a time until the dough clumps together. You’re aiming for a dough that just holds together and isn’t sticky, so try not to overwork it or the biscuits can turn out tough.
Wrap the dough and chill for 30 minutes so it firms up and is much easier to roll.
Preheat the oven to 180ºc/160ºfan and line 2-3 large trays with paper.
Lightly flour the work surface
Roll the dough out into a large rectangle, until it’s about 1/2cm thick all over. Keeping it even is what helps every biscuit bake at the same rate.
Cut the dough into biscuits, and gently press a patterned cutter to mark the tops if you’re using one.
Carefully place each biscuit onto the lined trays, spaced apart slightly.
Bake for 10-11 minutes. They’ll still feel a little soft in the middle but will firm up as they cool, so don’t be tempted to over bake them.
Remove from the oven and leave to cool fully on the tray before filling.
Filling
Add the room temperature butter to a large bowl and beat until soft and pale.
Add the icing sugar and cocoa powder and beat again until smooth.
Add the vanilla, and 1 tbsp of whole milk at a time until you reach a smooth and pipeable consistency.
On half of the biscuits, pipe a generous amount of buttercream, then sandwich with a second biscuit and press gently so the filling just reaches the edges. Leave to set for a few minutes before serving.