For all the attention student loans have received in the media and from policymakers in recent years, there is still remarkably little information on why and how borrowers struggle to repay them. Rising college prices and debt levels explain some of the troubles borrowers have with their loans, as does a slow economic recovery that has caused unemployment and underemployment. To seek a broader explanation of student loan struggles, "New America's Education Policy Program" commissioned a series of six focus groups that met between June and October 2014. Groups met in Philadelphia, Boston, Phoenix, San Francisco, Chicago, and Atlanta and included a total of 59 student loan borrowers. Participants were selected based on a range of characteristics regarding their self-reported repayment histories, but all indicated they had at some point struggled to repay their student loans. This paper provides a broad and objective look at struggling borrowers, and spotlights specific explanations and details that participants provided about their borrowing and repayment experiences that may be surprising to the federal policy community. [The New America Education Policy Program's work is made possible through generous grants from the Alliance for Early Success; the Annie E. Casey Foundation; the Bill and Melinda Gates Foundation; the Grable Foundation; the Foundation for Child Development; the Joyce Foundation; the Kresge Foundation; Lumina Foundation; the Pritzker Children's Initiative; the William and Flora Hewlett Foundation; and the W. Clement and Jessie V. Stone Foundation.]