Large Language Models (LLMs) are increasingly deployed in finance, where unsafe behavior can lead to serious regulatory risks. However, most red-teaming research focuses on overtly harmful content and overlooks attacks that appear legitimate on the surface yet induce regulatory-violating responses. We address this gap by introducing a controllable black-box multi-turn risk-concealed redteaming framework (CoRT) that progressively conceals surface-level risk while exploiting regulatory-violating behaviors. CoRT contains two key components: (i) a Risk Concealment Attacker (RCA) that generates multiturn prompts via iterative refinement, and (ii) a Risk Concealment Controller (RCC) that predicts a turn-level Risk Concealment Score (RCS) to steer RCA’s follow-up style. We also build a domain-specific benchmark, FinRisk-Bench, with 522 instructions spanning six financial risk categories. Experiments on nine widely used LLMs show that CoRT (RCA) achieves 93.19% average attack success rate (ASR), and CoRT (RCA+RCC) further improves the average ASR to 95.00%. Our code and FinRisk-Bench are available at https://github.com/gcheng128/CoRT.