Infrastructure as Code (IaC) tools have transformed the way IT infrastructure is automated and managed, but their growing adoption has also exposed numerous challenges for practitioners. In this paper, we investigate these challenges through the lens of Ansible, a popular IaC tool. Using a mixed methods approach, we investigate challenges faced by practitioners. We analyze 59,157 posts from Stack Overflow, Reddit, and the Ansible Forum to identify common pain points, complemented by 20 semi-structured interviews with practitioners of varying expertise levels. Based on our findings, we highlight key directions for improving Ansible, with implications for other IaC technologies, including stronger failure locality to support debugging, clearer separation of language and templating boundaries, targeted documentation, and improved execution backends to address performance issues. By grounding these insights in the real-world struggles of Ansible users, this study provides actionable guidance for tool designers and for the broader IaC community, and contributes to a deeper understanding of the trade-offs inherent in IaC tools.