DuSE-Bench: Benchmarking Joint Reasoning over Evolving Dialogue and Documents

AI systems increasingly need to combine two demanding capabilities: navigating multi-session conversation history and performing deep reading comprehension within long documents. Yet no existing benchmark evaluates both simultaneously. We introduce MemoryDocDataSet, a synthetic benchmark of 50 micro-worlds and 1,000 QA pairs in which each instance comprises 3-5 personas, a temporal event graph spanning months of activity, 3-5 real long documents (20,000-50,000 tokens each sourced from the Caselaw Access Project), multi-session conversations grounded on those documents, and 20 question-answer pairs across five reasoning categories. The defining feature is the Hybrid source tag: questions requiring a system to first navigate conversation history to identify which document is relevant, then extract the answer from within that document. Hybrid questions account for 75.1% of the dataset. Dataset quality is characterised through a prompt-sensitivity self-consistency analysis using LLM-as-judge, yielding a median Cohen's $κ= 0.634$ across all 50 micro-worlds. We evaluate six baseline configurations spanning truncated context, long-context LLMs, retrieval-augmented generation (RAG), and memory systems. The best baseline (RAG-Both) achieves 0.358 overall F1 and 0.342 on Hybrid. Document-only retrieval (RAG-Doc) collapses to 0.267 on Hybrid despite achieving 0.453 on Doc-only questions, demonstrating a clear joint-retrieval gap that motivates architectures unifying conversational memory with long-document navigation. We release the dataset, generation pipeline, and all baseline implementations.

With the emergence of search-enabled generative QA systems, users are increasingly turning to tools that browse, aggregate, and reconcile evidence across multiple sources on their behalf. Yet many widely used QA benchmarks remain answerable by retrieving a single relevant passage, making them poorly suited for measuring cross-source sensemaking, such as integrating evidence, tracking causal links, and resolving dependencies across facets of a topic. We present iAgentBench, a dynamic ODQA benchmark that targets these higher-level information needs while keeping questions natural and grounded in realistic information-seeking behavior. iAgentBench draws seed topics from real-world attention signals and uses common user intent patterns to construct user-like questions whose answers require combining evidence from multiple sources, not just extracting a single snippet. Each instance is released with traceable evidence and auditable intermediate artifacts that support contamination checks and enable fine-grained diagnosis of failures in retrieval versus synthesis. Experiments across multiple LLMs show that retrieval improves accuracy, but retrieval alone does not reliably resolve these questions, underscoring the need to evaluate evidence use, not just evidence access.

Enterprise agents answer questions over workplace records that evolve through team collaboration. As information is shared, corrected, and revised across documents, chats, and figures, multiple versions of the same information accumulate in the workspace. Reliable question answering therefore requires agents to reason over sufficient evidence, resolve cross-source and temporal conflicts, and recognize when the available evidence is insufficient to establish an answer. To systematically evaluate these capabilities, we introduce MMEnterprise-Bench, a benchmark comprising 1,613 questions grounded in evolving multimodal records from simulated collaboration projects, covering three categories: Evidence Reasoning, Conflict Resolution, and Unanswerability. We evaluate 10 proprietary and open-source multimodal LLMs and find that even the strongest models struggle when evidence contains cross-source or temporal conflicts or spans multiple images. Moreover, increasing the retrieval budget or employing a larger retriever improves evidence recall but does not consistently translate into higher answer accuracy. These findings highlight the persistent challenges of reasoning over evolving workplace records and establish MMEnterprise-Bench as a testbed for developing more reliable enterprise agents. Code and data are available at https://mlvlab.github.io/MMEnterprise-Bench/.