Little information exists about the daily lives of women who are grandmothers, and the differences in daily stresses based on caregiving status to grandchildren. This content analysis examines the stresses of 64 grandmothers as grouped by caregiver status (grandmothers raising grandchildren, grandmothers living in multigeneration homes, non-caregivers to grandchildren) as recorded in three-week diaries. The nature of salient issues and stressful interactions differed by caregiver groups. Grandmothers raising grandchildren reported more stresses related to grandchildren's routines, activities, and school progress, more time pressure, and difficult interactions with grandchildren. The diary entries of grandmothers in multigenerational homes reflected their supplemental role in childcare, and sometimes stressful interactions with other family members. Grandmothers with no routine caregiving to grandchildren reported more involvement with those outside the immediate family. Many general concerns about the well-being of the family represent commonalities in grandmothers despite differences in current caregiving roles to grandchildren.