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Yes, you can do German schmear on stone. You can account for the more textured and rough surface of stone by using a large paintbrush instead of a putty knife. A brush allows you to drag mortar across the stone to get it into all the cracks and crevices. However, a brush will cover more of the surface, so you may need a wet sponge to scrub excess mortar and expose more of your stone.

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.

When painting brick, each application method has distinct advantages and disadvantages. Spraying is significantly faster but may not penetrate deeply beyond the surface layer. Rolling is effective for working paint into the brick's texture but can be less effective on mortar joints. If you opt for a roller, choose a thick nap of at least a half-inch to ensure paint gets into all the crevices for even coverage. Using a brush is generally not recommended as it is very time-consuming and provides poor surface penetration. Ultimately, a combination of spraying followed by back-rolling is often the best strategy for a durable and even finish.

No, it’s not recommended to attach shutters to brick without drilling. Brick is dense and built to last, so adhesives and shortcut methods don’t usually cut it. Even heavy-duty glue struggles to hold up over time—especially against wind, moisture, and temperature changes. Most no-drill options are made for materials like vinyl or wood, not solid masonry. Skipping the drill might seem easier, but it puts your shutters—and anything below them—at risk. For a secure, lasting install, drilling is the way to go. It takes more effort up front, but the result is safer and more reliable.