The condition of long-term homelessness has been demonstrated to affect a far smaller number of individuals compared with those who exit and become housed. It is nonetheless a pressing policy concern because of the high social and economic costs associated with prolonged homelessness. As with much homelessness research generally, gender is not adequately addressed, and frequently ignored, within analyses of ‘long-term’ or ‘chronic’ homelessness. This paper seeks to redress this imbalance and examines the experiences of women who have lengthy homeless histories based on the accounts of 34 women who are participants in a larger biographical study of homeless women in Ireland. Women's movements into and out of homeless service settings are examined in some detail, as are their accounts of the lived experience of prolonged homelessness. Their narratives reveal their mothering roles and identities, intimate relationships and intimate partner violence, and their ongoing interactions with institutional settings, including homeless hostels, as key dynamics influencing their movements and the strategies used by them as they attempt to manage their homelessness. We conclude by highlighting several gender-specific forces driving the women's experiences of unresolved homelessness. A number of key messages for policy are also discussed.