Diabetes prevalence has steadily been increasing over the last decades and is expected to continue in this trajectory. Diary keeping is considered the central part of any successful therapy. Since paper-based diary keeping is often poor and electronic diaries often challenging for elderly users, we developed Diabetto. Using focus groups and interviews we analyzed the requirements for Diabetto. It uses a LiveScribe Echo pen as a replacement for a regular pen in traditional paper-based diary keeping, while at the same time adds interactive therapy support and access to a nutrition database through pen-input and text-to-speech. By enhancing an al- ready familiar process we managed to achieve a high acceptance of the device. In an experimental evaluation using an extended TAM model we analyzed the influence of user-diversity factors on the acceptance. Interest- ingly typical predictors of acceptance, such as efficiency during use, did not influence ease of use, indicating that the digital pen might not be perceived as computerized technology.