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Step 1
Heat 1 Tbsp. oil in a large skillet over high. Cook beef, breaking up with a wooden spoon, until browned but not completely cooked through, 5–7 minutes. Transfer to a medium bowl with a slotted spoon.
Step 2
Reduce heat to medium and add remaining 1 Tbsp. oil to skillet. Cook onion, tomatoes, chile, garlic, cumin, pepper, and 1 Tbsp. Diamond Crystal or 1¾ tsp. Morton kosher salt, stirring, until tender but not browned, about 5 minutes. Return beef along with any juices to pan and add potato and stock. Bring to a simmer and cook, stirring and scraping up browned bits, until potato is tender and beef is cooked through, 20–25 minutes. Season with more salt if needed.
Step 3
Mix in cilantro just before serving.
Step 4
Do Ahead: Picadillo (without cilantro) can be made 3 months ahead. Transfer to an airtight container and freeze.