Large language models (LLMs) have evolved into interactive agents that collaborate with users in real-world tasks. Effective collaboration in such settings increasingly depends on understanding the user beyond what is explicitly stated, as user intent is often reflected in fragmented daily interactions and requires both personalized modeling and proactive interaction. However, existing agent benchmarks primarily evaluate reasoning and tool use, largely overlooking the challenges of inferring and leveraging user preferences in realistic scenarios. To address this gap, we introduce VitaBench 2.0, a benchmark for evaluating personalized and proactive agent behavior in long-term user interactions. In VitaBench 2.0, tasks are organized as temporally ordered sequences for individual users, where preferences are embedded in fragmented and heterogeneous interactions. Successful completion of tasks requires the agent to continuously extract, utilize, and update user preferences from these interactions. We further evaluate proactiveness through tasks that require agents to recognize missing information and actively acquire it from users or environments before making decisions. To support systematic analysis, we provide an extensible memory interface that enables controlled comparison across different memory architectures. We benchmark a diverse set of frontier proprietary and open-source LLMs. Results show that real-world personalization remains highly challenging even for state-of-the-art models, revealing a substantial gap between current capabilities and practical requirements. Extensive analysis further reveals the failure modes and capability bottlenecks of current agents in real-world personalized decision-making, providing insights for future model improvements.