<p>As the world of technology advances, so do the tools that software developers use to create new programs. In recent years, software development tools have become more popular, allowing developers to work more efficiently and produce higher-quality software. Still, installing such tools can be challenging for novice developers at the early stage of their careers, as they may face issues such as compatibility problems (e.g., with operating systems) and unclear instructions. Therefore, this work aims to investigate the challenges novice developers face when installing software development tools and the strategies they employ to overcome them. To investigate these, we conducted an analysis of 24 live software installation sessions to observe the difficulties developers encounter, the strategies they apply, and the types of information sources they consult when facing obstacles. We also conducted a validation survey with 144 students to support and expand our findings. Our results reveal recurring challenges such as unclear or dysfunctional documentation, complicated installation processes, version incompatibility, and lack of feedback during installation. To address these, participants used strategies such as reformulating search queries, reading instructions more carefully, and searching for alternative sources of documentation. These sources included community platforms (e.g., Stack Overflow), video tutorials, blog posts, and official documentation. Based on these findings, we provide practical recommendations for tool vendors, tool users, and researchers to improve the installation experience for novice developers.</p>