Open source software plays an important role in the software supply chain, allowing stakeholders to utilize open source components as building blocks in their software, tooling, and infrastructure. But relying on the open source ecosystem introduces unique challenges, both in terms of security and trust, as well as in terms of supply chain reliability. In this dissertation, I investigate approaches, considerations, and encountered challenges of stakeholders in the context of security, privacy, and trustworthiness of the open source software supply chain. Overall, my research aims to empower and support software experts with the knowledge and resources necessary to achieve a more secure and trustworthy open source software ecosystem. In the first part of this dissertation, I describe a research study investigating the security and trust practices in open source projects by interviewing 27 owners, maintainers, and contributors from a diverse set of projects to explore their behind-the-scenes processes, guidance and policies, incident handling, and encountered challenges, finding that participants’ projects are highly diverse in terms of their deployed security measures and trust processes, as well as their underlying motivations. More on the consumer side of the open source software supply chain, I investigated the use of open source components in industry projects by interviewing 25 software developers, architects, and engineers to understand their projects’ processes, decisions, and considerations in the context of external open source code, finding that open source components play an important role in many of the industry projects, and that most projects have some form of company policy or best practice for including external code. On the side of end-user focused software, I present a study investigating the use of software obfuscation in Android applications, which is a recommended practice to protect against plagiarism and repackaging. The study leveraged a multi-pronged approach including a large-scale ...