The disruption of the biological family unit due to divorce or separation followed by remarriage or re-partnering has a profound impact on every family member, including extended family members. An individual can become a stepgrandparent through later life re-partnering, when an adult child becomes a stepparent, or when a stepchild becomes a parent. In order to gain a greater understanding of the communication influencing the development and maintenance of stepgrandparent roles and identity, an interpretive phenomenological analysis (IPA) method was employed to guide the researcher through interviews with adult stepfamily members across two generations of stepfamily membership: stepparents and stepgrandparents. Interview data from 41 research participants revealed seventeen themes related to the three ways an individual may become a stepgrandparent. Findings indicate the experience of becoming a stepgrandparent as the result of an adult child becoming a stepparent is the most challenging while the experience of becoming a stepgrandparent as the result of a long-term stepchild becoming a parent is the least challenging.