Elders usually experience high levels of loneliness in the society as they have retired from work and less of a center within the family. There are many interaction design work that target elder’s loneliness and aim to solve the problem by connecting elders with other people through distance. Digitalization’s connectedness is a helpful factor that can combat elder’s communication issues. At the same time, there are many already existing digital services that embed communication functions such as email, texting, and video call. Still, elders find themselves have difficulties using existing technology. The thesis focuses on why current digital technologies cannot help elders connect and communicate efficiently and how to re-design to help elders feel their willingness to communicate by current technologies. Empirical research in the thesis project has shown that elders lack trust towards digital systems due to lack of transparency and findings of specialized contexts. The project is in two parts: qualitative research and prototyping. Through qualitative research, the thesis shows that there is a lack of transparency and control from digital applications that elders experience. Prototyping outcomes suggests enabling personalization within digital services for elders by implementing slow user interactions and simple graphic elements.