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You should generally drill into the mortar joints when installing shutters on brick. Mortar is softer, which makes drilling easier and puts less strain on your tools. It also lowers the risk of cracking a brick—something that’s a lot harder to fix. Mortar holds fasteners well enough for standard shutters, and if you ever need to patch the holes later, it’s a much simpler job than dealing with damaged brick. Just keep in mind that if your mortar joints are too thin or the hardware calls for brick anchoring, you'll need to check the manufacturer’s recommendations and adjust accordingly.

Drilling into brick doesn’t have to be a dangerous project if you prep and approach it with the right tools and techniques, but it does come with risks if it’s not done correctly. It can lead to significant issues, such as damaging the brick or affecting the wall’s structural integrity. Applying too much force can crack or chip the brick, while incorrect placement might compromise its load-bearing strength. 

Professionally done brick repointing can last 20 to 30 years, sometimes longer. However, the exact lifespan depends on several factors, including the quality of the mortar, the skill of the mason, and exposure to weather. If you live in an area with harsh weather or frequent freeze-thaw cycles, you may need to repoint more often. Repointing that is done as a DIY project may only last 10 to 15 years. It's time to repoint when you notice signs of mortar failure, such as crumbling or missing mortar, holes, or vines growing between the bricks. Regular inspections can help you catch these issues early.

Modern brick houses are really stick-built homes with a brick facade for aesthetic purposes only, so most have framing. With genuine brick construction, most homeowners install furring strips over the interior of the brick and then install drywall over those strips to cover the brick wall, so they don’t have traditional framing.