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Place the dried chiles in a bowl and cover with hot water. Let them soak for 15 minutes, until softened.
While the chiles soak, add the cumin, coriander, oregano, black peppercorns, kosher salt, and annatto seeds to a spice grinder, or high powered blender, or mortar and pestle. Grind until fine. If using achiote paste, skip this step and just add it to the blender later.
Drain the soaked chiles and add them to a blender along with the chipotles, garlic, ground spices, salt, pineapple juice, vinegar, and oil. Blend until smooth. Add a splash of water or more pineapple juice if needed to loosen it up.
Give it a taste; it should be tangy, smoky, a little sweet, and well-seasoned. Add more salt or chipotle peppers, if needed. Let it sit for 10 minutes before using to let the flavors settle.