Families have a strong need to connect with their loved ones over distance. However, most technologies do not provide the same feelings of connectedness that one feels from seeing remote family members. Hence our goal was to understand if a video connection, in the form of a media space, could help families feel more connected and what design factors would be critical for its success. To answer this, we designed a video media space called the Family Window and deployed it within the homes of two families for eight months and four families for five weeks. Our results show that always-on video can lead to an increase in feelings of connectedness by providing availability awareness and opportunities for sharing everyday life. However usage and value of such media spaces hinges on close-knit relationships and control over one's autonomy.