To assist users in complex tasks, LLMs generate plans: step-by-step instructions towards a goal. While alignment methods aim to ensure LLM plans are helpful, they train (RLHF) or evaluate (ChatbotArena) on what users prefer, assuming this reflects what helps them. We test this with Planorama: an interface where 126 users answer 300 multi-step questions with LLM plans. We get 4388 plan executions and 5584 comparisons to measure plan helpfulness (QA success) and user preferences on plans, and recreate the setup in agents and reward models to see if they simulate or prefer what helps users. We expose: 1) user/model preferences and agent success do not accurately predict which plans help users, so common alignment feedback can misalign with helpfulness; 2) this gap is not due to user-specific preferences, as users are similarly successful when using plans they prefer/disprefer; 3) surface-level cues like brevity and question similarity strongly link to preferences, but such biases fail to predict helpfulness. In all, we argue aligning helpful LLMs needs feedback from real user interactions, not just preferences of what looks helpful, so we discuss the plan NLP researchers can execute to solve this problem.