I found that my problem was unclear instruction about the timing between jumping and popping. One day when I was watching a slowmo ollie video though, I noticed that the skateboarder already was beginning to jump (at least his body was already going in an upward motion) before snapping the board off the ground. That was a critical change I needed to make in order to get it working. I had been trying to pop the board while all my weight was still pushing down on it (kind of an obvious mistake, but I somehow overlooked this). Hope this helps somebody.

A rushed take-off might be the problem here. Steps 2-4 of this trick tip could help you out. In order to make your feet “stick” to the board, you have to do the movement fluidly. But don’t stress yourself out! You should rather start with some preliminary exercises until you feel safe while ollieing. It is also important to pull your foot up to your board’s nose in a straight manner to prevent it from spinning.
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Before learning it, do have your riding basics down. Meaning you are very comfortable riding it around and doing kickturns and not be pushing mongo. Best to learn it whilst stationary with your wheels on a crack so that you don't move and slip out so much. I don't recommend doing it on grass or carpet cos when you pop the tail, it's gonna be absorbed by the floor and when you start doing it on pavement, your muscles will memorize a different way of doing it. So nope, no easy way out i guess.
Level out on the way down – Before you start to head back towards the safety of the earth, level your feet out as the board begins to fall. If you’re trying to jump a gap on your board, this will help you keep going straight and maintain your momentum. Alternatively, you can land on your nose or tail and perform a manual out of the jump, but those are pretty advanced moves. Might want to wait until those little pink training wheels are off your board first.
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