In a mini food chopper, combine canned tomatoes, chipotles, brown sugar, Cajun seasoning, half of the garlic, and half of the Mexican seasoning. Process until homogenous.
In a small bowl, combine remaining Mexican seasoning and half of the olive oil.
Using gloved hands, rub the olive oil mixture all over the short ribs, coating all sides.
Heat remaining olive in a Dutch oven over medium-high heat until shimmering. Add short ribs and sear well on both sides, there should be a nice crust.
Remove short ribs from the pan and set aside. To the hot pan add remaining garlic, the onion, beef bouillon base, apple cider vinegar, red wine, and the blended tomato mixture. Stir to combine and bring to a boil over medium-high heat.
When mixture is boiling, turn off the heat and nestle the short ribs into the liquid. Place lid on pan and bake in the oven for 3 hours.
Remove from oven and skim excess fat, if any. If you like, you can thicken the juices in the pan by adding a little cornstarch.
Notes
Choose well-marbled cuts of bone-in beef short ribs with plenty of fat which will enhance the flavor and and tenderness. You can find beef short ribs at most butcher shops, grocery stores, or meat markets. Look for ribs that are evenly sized and trimmed of connective tissue.
Chipotle in adobo sauce and the Cajun seasoning give the ribs heat. Feel free to add more chipotles in adobo sauce depending on your preferences.
While the Cajun seasoning is not traditionally Mexican-inspired, we love the extra tingly touch it adds. We also love using our homemade Mexican seasoning blend for this recipe because you can control the amount of each ingredient that goes into it.