Upset the apple cart Definition 1 of 1Pro Tip 1/3Unexpected Change Use when someone's actions unexpectedly change the course of events or plans. Jane came in with a new proposal and totally upset the apple cart. Pro Tip 2/3Negative Outcome Often used to describe actions that result in negative outcomes or chaos. Trying to change the rules now would upset the apple cart. Pro Tip 3/3Proceed Carefully Suggests being cautious to not disturb a balanced situation or relationship. I don't want to upset the apple cart by asking for too many changes.