In both cases, when you get it that wrong that your meaning doesn’t come across correctly, it’ll usually get pointed out to you, either by the compiler or the person you’re talking to, so you can go back and try again.
Eventually, you’ve potentially gotten it right when the compiler stops throwing errors or the person you’re speaking to understands. Unfortunately, in both cases you may still not end up with the desired outcome as your compiler is “stupid” and cannot understand intent, only what you’ve written. Similarly, but different, the human you’re speaking to may bore of your broken language eventually and just move on.
There’s no perfect system for everyone, but it never hurts to remember the saying: perfect is the enemy of good enough. It doesn’t matter if your language skills are perfect, just that they’re good enough to convey your meaning effectively for the environment you’re in.