there’s some great advice here from people about learning in a context dependent way from your Japanese friends and tutors.
I’d just add, just in case you haven’t discovered this through reading and conversation yet, this problem isn’t just kanji, it’s just about any word you look up in the dictionary for Japanese. Context like the formality, circumstances of speaker (gender, age, relative social standing), perspective of the situation (direction of action, objects/people involved, animate/inanimate), even what assumptions you’re making about the situation, etc, all of these things affect the word choice. Any word I’ve ever used after looking it up in a dictionary is corrected by my friend. So as others have said, it’s training me when I come across words whether in reading or conversation, look at the context. I’m trying to hoover up clues that I can attach to that word in my mind so that the next time I want to use it, I decide, does this “feel” similar? If I come across a new word in a newspaper, for example, I now know that is unlikely to be the word I use in conversation with my friend, and I should stick to the one I know and ask for the difference. Then after a while, I have enough of those “anchor” words, when I see a new word somewhere, I can guess how to categorise its context based on what other words are used in the same sentence. My friend also sent me a whole book on teineigo, keigo, and humble speech, that could be an area you could look into. Basically realising for every common word like 来る or 待つ there are 2-3+ other words depending on formality. All these things start to build up a feeling for things.
WK gives more context (with sentences and collocation examples) than most dictionaries, so I think actually they are doing ok on this point.
At least that’s my fuzzy memory before I moved on. I seem to remember the context sentences are actually ok and even the descriptors, I think the description for 翌日 says it’s formal use, right? It’s worth reviewing those now and then when you’re doing reviews and ask yourself - when is it appropriate to use this word? And when reviewing, tell yourself the context before marking it right. And if WK doesn’t explain it, look it up and add it in the custom notes field. I think their assumption is people would be reading a lot post level 20-30 or so and would build up that feeling. And while in my earlier days I didn’t think that was fair, actually, there is only so much you can learn theoretically. It’s a chicken and egg problem where vocab is properly useful in output after 1) you can remember it, and 2) you know how it’s used properly (context). Or is it 1) you know the context and 2) you can remember it? This is the problem you have, you know one and not the other. But the solution may not be more or better SRS, the brain will learn context best… in context.
Also, I hate to say it, but using a word embarrassingly out of context and being corrected is a great way to crystalise it perfectly after just one use. That’s gold.
