Preventing mentor-mentee relationships from ending prematurely is important because an early or unanticipated closure could lead to negative youth outcomes. In this study, the reasons for premature closure of a community-based mentoring program for youth with a visual impairment (VI) are studied. Data from 44 prematurely ended mentor-mentee pairs were analyzed; all mentees (M age = 18.5, SD = 1.92) and 23 of the mentors had VI. Logbook data with two types of transcribed semi-structured interviews were thematically coded line-by-line. Frequencies of coded responses provided insight into the most frequently reported reasons and the most frequently reported problems. Chi-square analyses were conducted to study differences between matches in the two conditions (i.e., matches containing mentors with or without VI). Regardless of the condition, premature closure was primarily initiated by mentees, and the most common cause was reported to be due to deficiencies in mentors' relationship skills. Matches with a mentor with VI experienced more problems within one domain of the International Classification of Functioning (ICF) model. These results show that additional pre-match mentor and supplementary mentee training are needed to increase relationship success in mentoring programs serving youth with VI.