Pour the milk into a bowl and add the raisins, stirring to coat them evenly. Let them sit for at least 10 minutes while you prep the other ingredients—this softens the raisins and adds moisture to the dough. While the raisins soak, preheat your oven to 375°F and prepare your baking sheets by lining them with parchment paper or silicone mats. This dual timing means nothing sits idle.

In a medium bowl, whisk together the whole wheat flour, rolled oats, baking powder, ground cinnamon, and salt. This combines all your dry components evenly, ensuring the leavening and spices distribute throughout the dough rather than clumping in spots. Set this mixture aside—I like to keep it near the mixing station so it's easy to grab when you need it.

In a large mixing bowl, beat together the softened butter, sugar, and honey until the mixture is light and fluffy, about 2-3 minutes. This creaming process incorporates air into the dough, which helps create tender cookies with a better crumb structure. The mixture should look pale and increased in volume when you're done.

Add the eggs one at a time to your creamed butter mixture, beating well after each addition to fully incorporate. Then pour in the vanilla extract and beat until everything is smooth and well-combined. This ensures the wet ingredients emulsify properly and create a cohesive batter.

Pour the dry ingredient mixture from Step 2 into your wet mixture from Step 4, then add the milk and plumped raisins from Step 1, stirring until just combined. Don't overmix—stir only until you don't see streaks of flour anymore. Overmixing develops gluten, which can make cookies tough. The raisins and their soaking liquid add moisture and subtle sweetness throughout the dough.

Drop spoonfuls of batter onto your prepared baking sheets, spacing them about 2 inches apart. Bake for 15 minutes, rotating the pans halfway through if your oven has hot spots. The cookies are done when the edges are set but the centers still look slightly soft—they'll firm up as they cool and stay tender inside.

Remove the cookies from the oven and let them cool on the baking sheets for 3 minutes—this lets them firm up enough to handle without breaking. Then use a spatula to transfer them to a cooling rack. I let them cool completely on the rack before storing them, which ensures they stay crispy on the outside and chewy inside.