Detecting prompt injection and jailbreak attacks is critical for deploying LLM-based agents safely. As agents increasingly process untrusted data from emails, documents, tool outputs, and external APIs, robust attack detection becomes essential. Yet current evaluation practices and production systems have fundamental limitations. We present a comprehensive analysis using a diverse benchmark of 18 datasets spanning harmful requests, jailbreaks, indirect prompt injections, and extraction attacks. We propose Leave-One-Dataset-Out (LODO) evaluation to measure true out-of-distribution generalization, revealing that the standard practice of train-test splits from the same dataset sources severely overestimates performance: aggregate metrics show an 8.4 percentage point AUC inflation, but per-dataset gaps range from 1% to 25% accuracy-exposing heterogeneous failure modes. To understand why classifiers fail to generalize, we analyze Sparse Auto-Encoder (SAE) feature coefficients across LODO folds, finding that 28% of top features are dataset-dependent shortcuts whose class signal depends on specific dataset compositions rather than semantic content. We systematically compare production guardrails (PromptGuard 2, LlamaGuard) and LLM-as-judge approaches on our benchmark, finding all three fail on indirect attacks targeting agents (7-37% detection) and that PromptGuard 2 and LlamaGuard cannot evaluate agentic tool injection due to architectural limitations. Finally, we show that LODO-stable SAE features provide more reliable explanations for classifier decisions by filtering dataset artifacts. We release our evaluation framework at https://github.com/maxf-zn/prompt-mining to establish LODO as the appropriate protocol for prompt attack detection research.

LLMs are increasingly used for code generation, but their outputs often follow recurring templates that can induce predictable vulnerabilities. We study \emph{vulnerability persistence} in LLM-generated software and introduce \emph{Feature--Security Table (FSTab)} with two components. First, FSTab enables a black-box attack that predicts likely backend vulnerabilities from observable frontend features and knowledge of the source LLM, without access to backend code or source code. Second, FSTab provides a model-centric evaluation that quantifies how consistently a given model reproduces the same vulnerabilities across programs, semantics-preserving rephrasings, and application domains. We evaluate FSTab on state-of-the-art code LLMs, including GPT-5.2, Claude-4.5 Opus, and Gemini-3 Pro, across diverse application domains. Our results show strong cross-domain transfer: even when the target domain is excluded from training, FSTab achieves up to 94\% attack success and 93\% vulnerability coverage on Internal Tools (Claude-4.5 Opus). These findings expose an underexplored attack surface in LLM-generated software and highlight the security risks of code generation. Our code is available at: https://anonymous.4open.science/r/FSTab-024E.