Recent advancements in generative AI have enabled ubiquitous access to large language models (LLMs). Empowered by their exceptional capabilities to understand and generate human-like text, these models are being increasingly integrated into our society. At the same time, there are also concerns on the potential misuse of this powerful technology, prompting defensive measures from service providers. To overcome such protection, jailbreaking prompts have recently emerged as one of the most effective mechanisms to circumvent security restrictions and elicit harmful content originally designed to be prohibited. Due to the rapid development of LLMs and their ease of access via natural languages, the frontline of jailbreak prompts is largely seen in online forums and among hobbyists. To gain a better understanding of the threat landscape of semantically meaningful jailbreak prompts, we systemized existing prompts and measured their jailbreak effectiveness empirically. Further, we conducted a user study involving 92 participants with diverse backgrounds to unveil the process of manually creating jailbreak prompts. We observed that users often succeeded in jailbreak prompts generation regardless of their expertise in LLMs. Building on the insights from the user study, we also developed a system using AI as the assistant to automate the process of jailbreak prompt generation.