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 challenges, such as compatibility issues (e.g., operating systems). Therefore, this work aims to investigate the challenges novice developers face in software development when installing software development tools. To investigate these, we conducted an analysis of 24 live software installation sessions to observe challenges and comprehend their actions, the strategies they apply, and the type of source of information they consult when encountering challenges. Our findings show that unclear documentation, such as installation instructions, and inadequate feedback during the installation process are common challenges faced by novice developers. Moreover, reformulating search queries and relying on non-official documentation were some of the strategies employed to overcome challenges. Based on our findings, we provide practical recommendations for tool vendors, tool users, and researchers.