Organizations are at varying stages in their accessibility journey with design systems, and while accessible components are beneficial, they do not automatically ensure accessible designs. Annotations play a crucial role in bridging this gap by providing explicit notes that convey design intent, helping to prevent accessibility issues and enhance the usability of digital experiences. The GitHub Annotation Toolkit, inspired by CVS Health's open-source kits, aims to streamline the annotation process and reduce overhead by integrating accessibility details into design components. Despite the benefits of design systems and annotations, accessibility is not a binary attribute, and ongoing refinement is necessary. GitHub has developed Preset annotations for their Primer components to document often-overlooked accessibility details, linking them to technical documentation to assist developers. This initiative underscores the importance of continuous testing and user feedback, particularly from those using assistive technology, to create truly accessible digital products.