Start small If you've never hit a rail, I recommend starting with a picnic table-type of box because they have a gradual up-ramp and a wide surface to help you get used to the feeling. Once you're ready, there are all kinds of rail designs out there, like the three-piece step-up and press boxes we built for the new Hyperlite video. There's always a chance to try something new with rails.
Focus on pressing Like everything else you do in wakeboarding, it's best to gradually work your way into pressing. Lean into it a little more each time so you can progressively get used to the feeling and avoid having the board slip out from under you. Always focus on holding your press across the entire rail.