The other day I found that they were struggling with "find me two synonyms of 'downloading' and 'extracting' that are the same length" because I was writing a script and wanted to see if could align the next path parameter.

First there's the tokenization issue, the same old "how many R in STRAWBERRY" where they are often confidently wrong, but I also asked not to mix tense (-ing and -ed for example) and that was very hard for them.