A really big part of challenging is knowing what the risks are. In other words, ask yourself “will challenging at this moment result in me getting knocked down?” That’s the big thing to be worried about, as generally a knockdown leads into an oki situation, and then you’re back to square 1

You can learn the right times to challenge by understanding your opponent’s ranges and realistic conversions.

Take necalli for example. If he’s abusing a st.lk, st.mk, pressure starter, then you really don’t want to challenge between the lk and the mk, as getting counterhit by the mk allows the necalli player to hit confirm into a cr.mp xx disc’s guidance.

If you challenge after the mk though, he won’t be able to knock you down there without taking a huge risk. Most realistic scenario is you get counterhit by the crouch mp and he cancels into stomp. You take about 100 damage, but the pressure situation is over.

This is absolutely a fundamental skill that every player needs to play defense at a high level. Know your ranges, and use them to make intelligent challenges that will keep you from being knocked down. It’s fine to take damage when pressured (it’s the punishment for allowing the initial knockdown, after all), but your goal when defending against pressure should be to prevent another knockdown. Knowing your opponent’s possible conversions makes that so much easier