Personally, I treat those sort of mistakes as "misunderstandings" where I wasn't clear enough with my first prompt, so instead of adding another message (and increasing context further, making the responses worse by each message), I rewrite my first one to be clearer about that thing, and regenerate the assistant message.
Basically, if the LLM cannot one-shot it, you weren't clear enough, and if you go beyond the total of two messages, be prepared for the quality of responses to really sink fast. Even by the second assistant message, you can tell it's having an harder time keeping up with everything. Many models brag about their long contexts, but I still feel like the quality of responses to be a lot worse even once you reach 10% of the "maximum context".