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Increasing numbers of older couples entering late-life remarriage will face dementia and spousal caregiving. This qualitative study, informed by grounded theory methods, is a first to explore spousal caregiving in the late-life remarried context. Interviews with nine late-life remarried wife caregivers identified complex intergenerational stepfamily dynamics that appear to amplify isolation and stress for this group of caregivers. Most women reported experiencing rejection of remarriage by adult children, minimal family involvement in caregiving, and intergenerational conflict regarding decision making. Nonetheless, caregivers described proactive, strategic approaches toward caregiving. This study examines the construct of boundary ambiguity as it relates to late-life remarriage and dementia caregiving, thus merging the unique challenges of caregiver and stepfamily dynamics. Findings are discussed in light of the potential risks highlighted for remarried couples facing chronic health issues. Future dementia research that accounts for diverse marital and family histories is suggested.