The promise of pervasive computing applications is to surround peo-ple with affordable, transparent and unobtrusive technology. However, several barriers including usability concerns, a lack of perceived usefulness, and low technology self-efficacy may jeopardize the successful adoption of ambient as-sisted living (AAL) systems, particularly by the elderly. Following the devel-opment of the SocialConnector system, which mediates and coordinates the communication effort of family members with their elders, this paper describes the iterative design process conducted to help improve the acceptance of the system by end-users. This process considered the implicit and explicit concerns and expectations of the intended target users, and it involved three improvement cycles along an action research approach. Through this process, we obtained a set of lessons learned that aim to describe how to unobtrusively introduce sens-ing and monitoring technology at the home of the elderly. Keeping simple yet meaningful interaction metaphors helps increase the learnability and perceived usefulness of AAL technology by the elderly.If older adults perceive the value of having such kinds of tools installed in their homes, then they are prone to as-sume them as part of their lives. Likewise, situational and activity awareness mechanisms, such as visual notification badges and audio-enhanced user inter-faces, can be used to persuade the elderly to approach the system and eventually use it. Finally, the design of AAL solutions also requires active consideration of the needs and attitudes of other family members, particularly those who assume an active role in the caring process of their elders.