Ten years after the popular birth of the internet, it is time for advocacy organizations to take stock of the lessons they have learned from experiments in using digital technologies to engage members and encourage activism. This paper reports on the results found from case studies of three advocacy organizations; the research reveals that staff members are conducting practical assessments of the benefits and drawbacks of new media use for cultivating a large and loyal membership. Though technologies such as email, the internet, Facebook, and Twitter enable groups to claim a large membership based on small actions, staff members understand that such tools can also potentially dilute what it means to be a member and what can be asked of members. To reconcile these trade-offs, advocacy organizations are crafting engagement plans that integrate on- and offline tools and strategies.