This study invited a pair of participants-a grandmother and her granddaughter-from a double-income family in the northern part of Taiwan to investigated parenting's content and challenges across a 4-year time period. The data was collected via semi-interviews and participant observation which obtained in 2002 and 2006 respectively. The result shows: grandparenting has expanded to supervising pre-school academic work, interpersonal relationships and character shaping apart from caring for childhood basic needs, safety and health care concerns. Even with the assistance from the neighborhood day-care centers or crammed schools to help with the schoolwork and respire, the aid and the support they can count on might be mainly from their own extended family.Grandparenting seems to be considered a close-to-the best option chosen under some inevitable circumstances, even though the effectiveness of nurturing might face daunting problems as the grandchildren grow up. If there's any problem occurred in the grandparent-grandchild relationship, the caretaker might be overwhelmed by the fatigue, powerlessness, and emotional burden. If this is the case, it is possible that the grandparents would ask their sons or daughters to go back to their ”parenting” position and the grandchildren would turn to their parents to seek more substantial security.