You need a solid 1/8 or 9/64 carbide drill bit to make a clean pilot hole,some hardware stores have them or check ebay. Then you enlarge it with a cobalt bit. I use a size drill bit that is slightly under a 1/4 -20 bolt size.,maybe start with a 7/32 . Then I use a 1/4-20 tap,that allows me to use a SS bolt without having to use a nut and drill all the way through the railing. Yes there is enough material on the railing that the bolt grabs the threads. I have also enlarged the factory hex set screws for the railings when they fail to work the same way.I sell tools for a living and a machinist customer turned me on to the solid carbide bit and it works 100 times better than colbalt for slippage and the pilot hole. Irwin makes the best consumer colbalt drill bit and they have two grades a m35 and 42 , 42 being the better grade but once you get the pilot hole either will do,stay away from harbor freight for those drill bits.