Yes, up to 2" long into the toughest woods. But there will be times it won't. Depending on the wood grain, sometimes an 18 gauge brad won't even drive in straight. Of course the shorter the pin, the more likely it will drive in straight. But the quality of the fastener is also extremely critical, especially for long pins. The carbon content of Grex pins are adjusted for each pin length to optimize its tensile strength. This maximizes its ability to penetrate straight into the wood. The precision manufactured parts on all Grex pinners also increase the chances of pins driving in straight. Also, by positioning the tool perpendicular to the wood grain, the chiseled end of the pins will tend to cut the grain instead of following it off to the side.