Prompt leakage in large language models (LLMs) poses a significant security and privacy threat, particularly in retrieval-augmented generation (RAG) systems. However, leakage in multi-turn LLM interactions along with mitigation strategies has not been studied in a standardized manner. This paper investigates LLM vulnerabilities against prompt leakage across 4 diverse domains and 10 closed- and open-source LLMs. Our unique multi-turn threat model leverages the LLM's sycophancy effect and our analysis dissects task instruction and knowledge leakage in the LLM response. In a multi-turn setting, our threat model elevates the average attack success rate (ASR) to 86.2%, including a 99% leakage with GPT-4 and claude-1.3. We find that some black-box LLMs like Gemini show variable susceptibility to leakage across domains - they are more likely to leak contextual knowledge in the news domain compared to the medical domain. Our experiments measure specific effects of 6 black-box defense strategies, including a query-rewriter in the RAG scenario. Our proposed multi-tier combination of defenses still has an ASR of 5.3% for black-box LLMs, indicating room for enhancement and future direction for LLM security research.