Digital home assistants (e.g., Amazon Echo) hold great potential to support older adults across a wide range of abilities to improve or maintain their quality of life. However, these devices and other related environmental control applications are not equipped with sufficient support for successful technology adoption among older adults. Without useful and usable information for guidance during the initial and continued use of these technologies (i.e., facilitating conditions), older adults may not sufficiently learn how to best utilize them, which is a primary barrier to technology adoption among this population. Our goal was to iteratively develop and test an instructional suite to support set up and use of an Amazon Echo Show and related connected technologies by older adults. Our human factors approach provides a roadmap to inform future instructional development for older adults to learn smart and connected technologies.