The purpose of freshmen orientation is "bridging the gap to college" (Tinto, 1993, p. 159). All college orientation programs have three objectives: provide information, set expectations, and provide social integration (Greenfield, Keup, & Gardner, 2013; Schofield & Sackville, 2010). Research supports a positive relationship between orientation and retention (Mullendore, 2014; Pascarella, Terenzini, & Wolfle, 1986; Perigo & Upcraft, 1989). There are students who do not attend traditional orientation and they perform less well academically at both the high school and college level (Abreu-Ellis, Knight, & Ellis, 2008). There is a lack of qualitative and mixed methods research regarding first-year students' transitions in relationship to orientation attendance. The purpose of this study was to investigate first-year students' transition to and future persistence in higher education related to their orientation attendance. This study was guided by theories of integration, involvement, and transition (Astin, 1977; Schlossberg, 1995; Tinto, 1975). An explanatory sequential mixed methods design was utilized. Participants included Fall 2016, Fall 2017, and Fall 2018 first-year students at a Midwestern, medium-sized, public four-year institution. These students reflected three types of orientation attendance: traditional, two-day orientation; non-traditional, one-day orientation; and no orientation. The quantitative findings replicated previous research. Students who attended traditional orientation did better academically than those who attended shortened orientation or did not attend orientation. Three themes were identified in the qualitative interviews: advanced high school opportunities were preparatory for college; connection is an important factor in college transition and success; and high school and college are different. The integration of how the qualitative themes informed the quantitative findings led to the following conclusions: (1) connection with friends, peers, and resources can aid the college transition. Students who do not attend traditional orientation, or do not connect with others at orientation, need to build connection in other ways; (2) advanced high school opportunities and orientation were helpful in the transition to college but neither adequately prepare students for college; and (3) first-year students will struggle and it is their ability to deal with the struggle that determines their success. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]