Large language models (LLMs) are increasingly expected to tackle complex tasks, driven by their expanding applications and users' growing proficiency in crafting sophisticated prompts. However, as the number of explicitly stated requirements increases (particularly more than 10 constraints), LLMs often struggle to accurately follow such complex instructions, which limits their applicability in complex real-world scenarios. To the best of our knowledge, existing datasets do not exceed 10 constraints per instance. To address this challenge, we propose RECAST, an efficient and scalable framework for synthesizing datasets where each example incorporates far more constraints than those in existing benchmarks, aiming to challenge and extend the boundaries of models' ability to follow complex instructions. These constraints are extracted from real-world prompt-response pairs to ensure practical relevance. Using this framework, we construct RECAST-30K, a large-scale, high-quality dataset comprising 30k instances spanning 19 constraint types. Experimental results demonstrate that models finetuned on RECAST-30K substantially improve in following complex instructions while maintaining their general capabilities without degradation. Moreover, RECAST enables automatic verification of constraint satisfaction via rule-based validators for quantitative constraints and LLM-based validators for qualitative ones; the verifiability provided by RECAST enables the design of reward functions for reinforcement learning, which further boosts model performance on complex and challenging tasks.
Instruction-following ability is critical for deploying large language models in real-world applications, where downstream components depend on the output satisfying specific constraints. Modern deployments increasingly handle the full task in a single LLM call, with one prompt specifying a layered output whose overall artifact, structural sections, and nested fields must each satisfy concrete constraints. Existing instruction-following benchmarks treat the constraint set as a flat list applied uniformly to the response, so they cannot scope a check to a particular section of the output. We introduce IFHierBench, a hierarchical instruction-following benchmark of 600 prompts stratified across four constraint-tree depths and 35 distinct constraints, each prompt paired with a deterministic checker that verifies satisfaction at every scope. Evaluating seven leading proprietary and open-weight models, we find that even the strongest model only marginally exceeds 50% prompt-level accuracy and that accuracy degrades sharply as constraint depth grows. Reliably following nested constraints remains a substantial gap for current LLMs, motivating future training methods that consider constraint adherence at finer granularity to achieve better instruction-following ability.
Evaluation protocols can lag behind LLM capabilities. Programmatically verified benchmarks cover narrow surface constraints, whereas real-world instruction following and agentic workflows require judging semantic, contextual, and policy-dependent behavior. We study expert-curated rubric-based evaluation as a unified mechanism for measurement and reinforcement-learning rewards across two settings: complex instruction following and enterprise agentic tasks. We identify rubric-design choices that affect reward quality, including maximum viable atomicity, intent-aware criterion design, and LLM-judge calibration. We introduce ComplexConstraints, an expert-curated instruction-following suite comprising a public 75-prompt benchmark with 1,559 rubric criteria and a disjoint 1,000-prompt training set, with 10-40 atomic criteria per prompt. Empirically, rubric rewards improve training in both fixed task datasets, such as ComplexConstraints, and stateful RL environments, such as CoreCraft. Training a 4B model on ComplexConstraints improves mean criterion pass rate by +15.5 pp on a held-out split, bringing it within 0.5 pp of the untrained baseline of a roughly 60x larger Qwen3 model, and the gains transfer to external benchmarks the model never saw during training: +8.4 pp on AdvancedIF and +10.1 pp on MultiChallenge. In CoreCraft, rubric-reward RL likewise transfers to out-of-distribution benchmarks (+4.5 pp BFCL, +7.4 pp tau^2-Bench, +6.8 pp Toolathlon). These results show that expert-authored rubrics provide effective evaluation targets and scalable reward signals for improving LLM instruction following and agentic behavior.
Large language models (LLMs) are increasingly expected to follow long lists of constraints in complex instructions, and synthesizing instructions from a reference document (i.e., back-translation) is a widely used method to measure/enhance LLMs' ability to follow complex instructions. However, this method introduces a critical loophole: the constraint synthesis model copies text from the reference as a very specific constraint and the evaluated LLM trivially satisfies the constraint by copying its text in the response. To address these issues, we propose UNSPECIFIC, a novel framework that synthesizes constraints common to two similar reference articles to reduce copy-pasting, selectively hardens only trivially satisfied constraints to balance difficulty and naturalness, and evaluates satisfaction on both the generated article and its summary to penalize superficial instruction following. Consequently, we built the UNSPECIFIC benchmark on news, story, and blog domains to analyze the copy-pasting behavior of LLMs. Our results show that our synthesized constraints are not only more challenging (e.g., the satisfaction rate of GPT-5 Mini drops from 90% to 78%) and natural (LLM win-rate gap improves by 30%) from a human perspective but also mitigate the copy-pasting. We also find that a large portion of constraints are satisfied superficially (i.e., not satisfied in the core narrative of the article). The code and datasets are released at https://github.com/JeetDSharma/UNSPECIFIC.