Just-in-time Information Recommendation (JIR) is a service designed to deliver the most relevant information precisely when users need it, , addressing their knowledge gaps with minimal effort and boosting decision-making and efficiency in daily life. Advances in device-efficient deployment of foundation models and the growing use of intelligent wearable devices have made always-on JIR assistants feasible. However, there has been no systematic effort to formally define JIR tasks or establish evaluation frameworks. To bridge this gap, we present the first mathematical definition of JIR tasks and associated evaluation metrics. Additionally, we introduce JIR-Arena, a multimodal benchmark dataset featuring diverse, information-request-intensive scenarios to evaluate JIR systems across critical dimensions: i) accurately inferring user information needs, ii) delivering timely and relevant recommendations, and iii) avoiding irrelevant content that may distract users. Developing a JIR benchmark dataset poses challenges due to subjectivity in estimating user information needs and uncontrollable system variables affecting reproducibility. To address these, JIR-Arena: i) combines input from multiple humans and large AI models to approximate information need distributions; ii) assesses JIR quality through information retrieval outcomes using static knowledge base snapshots; and iii) employs a multi-turn, multi-entity validation framework to improve objectivity and generality. Furthermore, we implement a baseline JIR system capable of processing real-time information streams aligned with user inputs. Our evaluation of this baseline system on JIR-Arena indicates that while foundation model-based JIR systems simulate user needs with reasonable precision, they face challenges in recall and effective content retrieval. To support future research in this new area, we fully release our code and data.