The Lana'i Community Health Center (LCHC) like other health care organizations, is striving to implement technology-enabled care (TEC) in the clinical setting. TEC includes such technological innovations as patient portals, mobile phone applications, wearable health sensors, and telehealth. This study examines the utilization of communication technology by members of the Lana'i community and LCHC staff and board members in the home and in their daily lives and evaluates the community's electronic health literacy. Quantitative surveys and qualitative focus groups were utilized. These revealed that members of the Lana'i community and LCHC staff and board members regularly utilize technology, in the form of smart cell phones, WiFi, and internet texting. This community has integrated technology into their daily lives, even though they live on an isolated island with 3,102 people; however, despite this integration, the electronic health literacy of this population appears insufficient for proper understanding and utilization of TEC, limiting the potential of patient portals or remote monitoring of patient generated data for chronic disease prevention and management without additional education and mentoring. It is therefore in the best interest of the LCHC and other health organizations wishing to implement TEC in a rural community such as Lana'i to include a strong educational component with use of TEC, and perhaps establish a mentor/partnership program for the highly-challenged patient.