Preventive healthcare services require consumers to coordinate and manage several healthcare activities with multiple service providers. In this paper we set out to understand what challenges people face in managing personal healthcare requirements. We conducted a qualitative study of consumers who participate in a preventive care program called the Health Enhancement Program in the State of Connecticut. Data from the interviews of 15 participants of this program highlighted several challenges faced by participants in scheduling and managing their healthcare requirements. While some of the challenges were due to lack of communication between several stakeholders of the process, others provide implications for design of technology that can support management of personal healthcare requirements.