Information technology is essential to today’s manufacturing systems, but it makes them more vulnerable to cyber security threats than ever before. This chapter discusses the challenges to developing automatable configuration checklists for manufacturing environments using the Security Content Automation Protocol (SCAP) family of standards. Increased use of SCAP in manufacturing environments could reduce security vulnerabilities and the likelihood of damaging cyber attacks on manufacturing systems. However, complex relationships and dependencies within and between checklist rules, checking instructions and software result in platform fragmentation. Platform fragmentation makes it difficult to reuse or repurpose existing SCAP-expressed checklist content. Recent research and technological developments can be leveraged to yield potentially promising approaches for mitigating platform fragmentation and improving reuse.