Planning is a common yet complex activity shaped by constraints to satisfy and preferences to balance. Travel planning, as both an everyday activity and a frequent benchmark for evaluating intelligent systems, offers a rich context for examining how constraints and preferences emerge and evolve. While recent AI systems have achieved impressive results in generating personalized itineraries, they often assume that users can articulate stable goals upfront. To understand how real-world planning unfolds, we conducted a two-part interview study: one with eight travelers reflecting on their planning experiences, and one with nine travel agents sharing professional practices. We trace the dynamics of constraints and preferences as they are surfaced, refined, and coordinated throughout the planning process, and identified 11 actions revolving around constraints and preferences, which shaped the planning process. We offer design heuristics for planning tools that better support human-AI collaborative actions to support the fluid, contingent nature of planning.

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