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You will repoint over a fraction of the old mortar, but you should scrape away 1/2 to 1 inch of mortar from the joints before repointing. Otherwise, the repointing is only masking the weakened mortar instead of actually replacing it, which could put your chimney at risk of bigger, more expensive damages later on.

Removing paint from brick can have both aesthetic and practical value. Some people prefer the timeless look of bare brick, making it worthwhile to remove old paint layers. Brick also lasts longer when unpainted, as paint traps moisture, causing the brick to deteriorate more quickly. If your brick walls are already in bad shape, stripping the paint off might do more harm than good.

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 or mortar requires the use of a masonry drill bit. Masonry drill bits appear similar to standard drill bits except for the leading tip of the bit. The tip has a bulky carbide arrow-shaped end slightly larger than the rest of the bit shaft. Standard or high-speed drill bits designed for making holes in wood or metal don’t have the ruggedness or design shape you need to drill into brick. They may not go through the brick at all, and if they do, they’re more likely to overheat, crack, or dull before you finish drilling.