The same real-life questions posed to different individuals may lead to different answers based on their unique situations. For instance, whether a student is eligible for a scholarship depends on eligibility conditions, such as major or degree required. ConditionalQA was proposed to evaluate models’ capability of reading a document and answering eligibility questions, considering *unmentioned* conditions. However, it is limited to questions on single documents, neglecting harder cases that may require *cross-document reasoning* and *optimization*, for example, “What is the maximum number of scholarships attainable?” Such questions over multiple documents are not only more challenging due to more context to understand, but also because the model has to (1) explore all possible combinations of unmentioned conditions and (2) understand the relationship between conditions across documents, to reason about the optimal outcome. To evaluate models’ capability of answering such questions, we propose a new dataset MDCR, which can reflect real-world challenges and serve as a new test bed for complex conditional reasoning that requires optimization. We evaluate this dataset using the most recent LLMs and demonstrate their limitations in solving this task. We believe this dataset will facilitate future research in answering optimization questions with unknown conditions.