The purpose of this case survey was to examine the reasons that students provide regarding why they are on academic probation and the efficacy of discussing the family life cycle among this group. Initially, a pilot population of 93 students on academic probation, who are a part of a multi-cultural community college in New York City, were surveyed during the spring 2005 semester. The pilot survey found that most of the students reported to be on academic probation because of having social problems. The pilot survey satisfied reliability and validity. During the fall 2005 semester, a revised survey was administered to 16 students on academic probation. Six were African American, two were Asian, six were Hispanic, one was West Indian, and one was Hispanic and African-American. These students attended an academic success workshop that was geared to assist them with meeting retention standards. Category variables such as: parental status, caregiver status, personal illness, family illness, employment, poor academic preparation, and mental health status, were used to probe responses. The survey was administered before the workshop, so their responses would not be influenced by the workshop materials. During the workshop, the researcher discussed ways of getting off probation, presented concepts of the family life cycle, and explored how to manage multi-tasking responsibilities for family-life, school, work, and personal needs. After the workshop, students were given a Likert scale to evaluate the workshop. The results of the survey reported that students were on academic probation because of ambiguity with managing multi-tasking role responsibilities in the areas of family life and social life. Fifteen students reported mental health issues, such as depression, anxiety, stress, and attention deficit disorder as impeding factors. The students found the workshop and the discussion of the family life cycle to be very beneficial. College students on academic probation should be educated on the family life cycle, healthy relationships, and how to manage multi-tasked responsibilities. This will help them venture into the first phase of self-efficacy. General systems theory argues that the sum of parts equals a whole. Thus, family life, employment responsibilities, job satisfaction, healthy partner relationships, and educational attainment will be the sum of parts that equals the individual, and in the realm of academia understanding these variables are vital for servicing the contemporary college student. Further research is needed for discussing the family life cycle among college students on academic probation.