In a medium bowl, add dried chiles and enough boiling water to cover completely. Let soak until softened, about 10 minutes. Drain well.
In a blender, add softened chiles, pineapple juice, white vinegar, achiote paste, garlic, oregano, cumin, cinnamon, cloves, 1 1/2 teaspoons salt, and 1/4 teaspoon black pepper. Process until smooth, about 30 seconds (you will have about 1 cup marinade).
Transfer the marinade to a large zipper-top plastic bag. Add chopped pork and mash to coat. Marinate at least 4 hours or overnight.
To cook the pork:
In a large skillet over medium-high heat, heat olive oil until shimmering. Add pork and pineapple and cook until pork registers 145 degrees on a thermometer, about 15 to 20 minutes. Stir occasionally. Drain if desired (a colander works well).
Season to taste with salt. Serve with warmed tortillas, onion, cilantro, and guacamole.
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Notes
Guajillo chiles: You can buy dry, mild-flavored Guajillo chiles at well-stocked grocery stores (even Walmart depending on where you live), Mexican grocery stores, and on Amazon. You can also substitute dried Pasilla chiles or even Ancho chiles (dried Poblano peppers).
Achiote paste: This bright red, flavorful paste is made from annatto seeds (the seeds of the Achiote tree). There is no good substitute. Mexican grocery stores will carry it (El Yucateco is a popular brand), or you can buy it on Amazon.
Mexican oregano: Mexican oregano has a lemony-citrus flavor, while Mediterranean oregano (Italian, Greek, or Turkish) can be sweet, bitter, or peppery depending on the variety. You can find Mexican oregano at Mexican grocery stores or on Amazon.
Pineapple: You can substitute an equal amount of fresh pineapple for the canned. You'll still need juice, though, so either choose the juiciest fruit you can find or seek out the small (6 ounce) cans of pineapple juice.
Yield: This recipe makes about 4 cups of Al Pastor meat (pork and pineapple mixed together), enough for 16 tacos (4 tacos per person).
Storage: Store leftovers covered in the refrigerator for up to 4 days.
Make ahead: The marinade can be blended up to 3 days in advance.