Recent advances in large language models (LLMs) have led to increasingly sophisticated safety protocols and features designed to prevent harmful, unethical, or unauthorized outputs. However, these guardrails remain susceptible to novel and creative forms of adversarial prompting, including manually generated test cases. In this work, we present two new test cases in mental health for (i) suicide and (ii) self-harm, using multi-step, prompt-level jailbreaking and bypass built-in content and safety filters. We show that user intent is disregarded, leading to the generation of detailed harmful content and instructions that could cause real-world harm. We conduct an empirical evaluation across six widely available LLMs, demonstrating the generalizability and reliability of the bypass. We assess these findings and the multilayered ethical tensions that they present for their implications on prompt-response filtering and context- and task-specific model development. We recommend a more comprehensive and systematic approach to AI safety and ethics while emphasizing the need for continuous adversarial testing in safety-critical AI deployments. We also argue that while certain clearly defined safety measures and guardrails can and must be implemented in LLMs, ensuring robust and comprehensive safety across all use cases and domains remains extremely challenging given the current technical maturity of general-purpose LLMs.