Living with family and friends is a common strategy used to prevent or exit homelessness, but little is known about structural barriers that impede family and friends' ability to provide temporary or permanent housing for older homeless adults. We conducted semi-structured interviews with 46 homeless participants from the HOPE HOME study, a cohort of 350 community-recruited homeless adults age 50 or older in Oakland, CA, who reported having stayed with housed family/friends for 1 or more nights in the prior 6 months. We conducted semi-structured interviews with 19 hosts of homeless participants and 11 stakeholders in housing and homelessness. We found that homeless older adults and hosts perceived staying with family or friends as a form of temporary housing rather than as a permanent exit to homelessness. Structural barriers to family and friends providing housing for temporary stays or permanent exits from homelessness included housing regulations restricting visitors and changing rent obligations; decreased eligibility and priority for shelter and permanent housing; geographic and transportation challenges; and environments inconducive to older adults. We suggest four areas for policy reform: providing subsidies to hosts and homeless individuals, removing disincentives for homeless older adults to stay with family, changing lease regulations, and expanding the supply of affordable housing.