Context learning is an emerging inference-time task where LLMs must learn and apply novel, task-specific knowledge from intricate contexts absent from pre-training; even frontier models score under 24% task success. In this work, we conduct a comprehensive empirical study to understand why this setting remains difficult. A natural hypothesis is that failures stem from content access; yet across twelve retrieval, reflection, and verification baselines on CL-Bench, an extensive context learning benchmark, we find limited gains over direct full-context prompting. Further failure analysis reveals a key finding: unlike typical long-context tasks such as long document understanding, context learning requires not only recovering local content but also acquiring local specifications that are often unspecified in the query but distributed across the context: domain-specific formats, local rules, and completeness conditions. Across all 31,592 rubric items, we find that 55.4% clearly evaluate specification acquisition, while only 22.6% evaluate content acquisition. Moreover, despite 76.7% of specifications being unspecified in the user query, 95.5% are traceable to the context, indicating these are learnable obligations rather than hidden requirements. To validate this diagnosis, we design a deliberately simple intervention PSCI (private specification-contract induction) which extracts local specifications and enforces them through adversarial checking and repair; PSCI achieves state-of-the-art 28.14% with GPT-5.1 (+5.59 pp absolute and +24.8% relative) on CL-Bench, replicated on Qwen3.5-27B (+5.28 pp) and Gemini 3 Pro (+6.17 pp). Seventeen ablations further isolate the role of task-specific specifications. Overall, our results suggest context learning hinges on not only content acquisition but also specification acquisition.
Many real-world tasks require language models (LMs) to reason over complex contexts that exceed their parametric knowledge. This calls for context learning, where LMs directly learn relevant knowledge from the given context. An intuitive solution is inference-time skill augmentation: extracting the rules and procedures from context into natural-language skills. However, constructing such skills for context learning scenarios faces two challenges: the prohibitive cost of manual skill annotation for long, technically dense contexts, and the lack of external feedback for automated skill construction, since there is no automatic signal to tell whether a proposed skill is helpful. In this paper, we propose Ctx2Skill, a self-evolving framework that autonomously discovers, refines, and selects context-specific skills without human supervision or external feedback. At its core, a multi-agent self-play loop has a Challenger that generates probing tasks and rubrics, a Reasoner that attempts to solve them guided by an evolving skill set, and a neutral Judge that provides binary feedback. Crucially, both the Challenger and the Reasoner evolve through accumulated skills: dedicated Proposer and Generator agents analyze failure cases and synthesize them into targeted skill updates for both sides, enabling automated skill discovery and refinement. To prevent adversarial collapse caused by increasingly extreme task generation and over-specialized skill accumulation, we further introduce a Cross-time Replay mechanism that identifies the skill set achieving the best balance across representative cases for the Reasoner side, ensuring robust and generalizable skill evolution. The resulting skills can be plugged into any language model to obtain better context learning capability. Evaluated on four context learning tasks from CL-bench, Ctx2Skill consistently improves solving rates across backbone models.