Difficulty is really tricky to get right, especially in a jam setting.
I think in a jam how OK it is for something to be difficult is usually directly proportional to how essential that difficulty is for communicating the unique twist that your game has... but even then it's hard.
In our game (https://itch.io/jam/gmtk-2019/rate/462193) there's some wordplay involved as the game progresses, but we've had people not realize how much choice they actually have in how certain scenes play out. There's a bit of challenge in listening to who is speaking and trying to figure out how they will interpret what you say, and that challenge ramps up as the game progresses.
But because the game looks sort of like a visual novel, I think that people don't always necessarily expect to be able to fail at all, let alone expect to be challenged.
I tried to foreshadow it in the writing with some early characters responding to you in ways you might not have wanted if you're not paying attention to how they're phrasing their question, but I do wonder how many people don't 'get it', and what I could change in the writing to improve it for people who don't.
Not to mention the general accessibility issues for people who struggle with the English language, etc. Wordplay is pretty brutal in that case.