Real-world planning problems require constant adaptation to changing requirements and balancing of competing constraints. However, current benchmarks for evaluating LLMs’ planning capabilities primarily focus on static, single-turn scenarios. We introduce Flex-TravelPlanner, a benchmark that evaluates language models’ ability to reason flexibly in dynamic planning scenarios. Building on theTravelPlanner dataset (Xie et al., 2024), we introduce two novel evaluation settings: (1) sequential constraint introduction across multiple turns, and (2) scenarios with explicitly prioritized competing constraints. Our analysis of GPT-4o and Llama 3.1 70B reveals several key findings: models’ performance on single-turn tasks poorly predicts their ability to adapt plans across multiple turns; constraint introduction order significantly affects performance; and models struggle with constraint prioritization, often incorrectly favoring newly introduced lower priority preferences over existing higher-priority constraints. These findings highlight the importance of evaluating LLMs in more realistic, dynamic planning scenarios and suggest specific directions for improving model performance on complex planning tasks.