Preheat the oven to 350°F with a rack in the center. Lightly grease an 8" square pan and line with a parchment sling.

In a medium bowl, whisk together the flour, sugar, baking powder, baking soda, and salt.

In a large mixing bowl, vigorously whisk the eggs and olive oil until emulsified; the mixture should look creamy and yellow.

Whisk in the milk, orange zest, orange juice, and vanilla.

While whisking, gradually add the dry ingredients to the wet; continue to whisk until well combined and no lumps remain.

Pour the batter into the prepared pan and bake for 45 to 50 minutes, until the cake is golden brown on top and springs back when gently pressed.

Remove the cake from the oven and transfer it to a wire rack; allow the cake to cool in the pan for 30 minutes.

Run an offset spatula around the edges of the pan, then transfer the cake out onto the rack and allow it to cool completely.

In a small saucepan, combine the cranberries and orange juice. Cook over medium heat, stirring frequently and using a spoon or spatula to smash the berries as they burst, until the mixture is thickened and jammy, 4 to 5 minutes total.

Using a rubber spatula, press the cranberry mixture through a fine-mesh sieve into a small bowl. (You should have about 3 tablespoons/40g.)

Add the vanilla, salt, and 1 cup (114g) of the confectioners’ sugar and whisk until smooth.

Whisk in up to ½ cup (57g) more confectioners’ sugar as needed until the glaze is the consistency of molasses.

Pour the glaze over the cooled cake, nudging it to cover the surface and letting it drip down the sides in spots.

Wait for the glaze to set, 15 to 20 minutes, before slicing and serving.