The Java platform and third-party open-source libraries provide various Application Programming Interfaces (APIs) to facilitate secure coding. However, using these APIs securely is challenging for developers who lack cybersecurity training. Prior studies show that many developers use APIs insecurely, thereby introducing vulnerabilities in their software. Despite the availability of various tools designed to identify API insecure usage, their effectiveness in helping developers with secure coding practices remains unclear. This dissertation focuses on two main objectives: (1) exploring the strengths and weaknesses of the existing automated detection tools for API-related vulnerabilities, and (2) creating better tools that detect, repair, and demonstrate these vulnerabilities. Our research started with investigating the effectiveness of current tools in helping with developers' secure coding practices. We systematically explored the strengths and weaknesses of existing automated tools for detecting API-related vulnerabilities. Through comprehensive analysis, we observed that most existing tools merely report misuses, without suggesting any customized fixes. Moreover, developers often rejected tool-generated vulnerability reports due to their concerns on the correctness of detection, and the exploitability of the reported issues. To address these limitations, the second work proposed SEADER, an example-based approach to detect and repair security-API misuses. Given an exemplar ⟨insecure, secure⟩ code pair, SEADER compares the snippets to infer any API-misuse template and corresponding fixing edit. Based on the inferred information, given a program, SEADER performs inter-procedural static analysis to search for security-API misuses and to propose customized fixes. The third work leverages ChatGPT-4.0 to automatically generate security test cases. These test cases can demonstrate how vulnerable API usage facilitates supply chain attacks on specific software applications. By running such test cases during software development and maintenance, developers can gain more relevant information about exposed vulnerabilities, and may better create secure-by-design and secure-by-default software. / Doctor of Philosophy / The Java platform and third-party open-source libraries provide various Application Pro- gramming Interfaces (APIs) to facilitate secure coding. However, using these APIs securely can be challenging, especially for developers who aren't trained in cybersecurity. Prior work shows that many developers use APIs insecurely, consequently introducing vulnerabilities in their software. Despite the availability of various tools designed to identify API insecure usage, it is still unclear how well they help developers with secure coding practices. This dissertation focuses on (1) exploring the strengths and weaknesses of the existing au- tomated detection tools for API-related vulnerabilities, and (2) creating better tools that detect, repair, and demonstrate these vulnerabilities. We first systematically evaluated the strengths and weaknesses of the existing automated API-related vulnerability detection tools. We observed that most existing tools merely report misuses, without suggesting any cus- tomized fixes. Additionally, developers often reject tool-generated vulnerability reports due to their concerns about the correctness of detection, and whether the reported vulnerabil- ities are truly exploitable. To address the limitations found in our study, the second work proposed a novel example-based approach, SEADER, to detect and repair API insecure usage. The third work leverages ChatGPT-4.0 to automatically generate security test cases, and to demonstrate how vulnerable API usage facilitates the supply chain attacks to given software applications.