The mortar wears out before the brick
Mortar is meant to be the softer, sacrificial part of a wall — it gives a little so the brick does not have to. After a few decades the joints crumble, and that is normal. Tuckpointing cuts out the old mortar and packs in fresh so the wall is solid again.
The screwdriver test
Run a screwdriver along a joint. If the mortar is hard and stays put, you are fine. If it crumbles, rakes out easily, or you see gaps and a little sandy pile at the base of the wall, the joints are done and water is getting in.
Matching is the whole job
Good tuckpointing is invisible. The new mortar should match the old in color, sand, and joint shape. Mortar that is too hard or the wrong color can actually damage old brick and will stand out for years, so the matching matters as much as the work.
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