Family Achievement Guilt (Piorkowski, 1981) is a term that refers to the guilt first-generation college students experience leaving their family behind during the transition to academia. Though family achievement guilt has been examined critically by scholars (Covarrubias & Fryberg, 2015; Covarrubias et al., 2020), little research exists examining family achievement guilt, and further, support for first-generation college students during their transition to academia through a clinical lens. The aim of this study was to examine the experience of family achievement guilt through a Contextual Family Therapy lens (Boszormenyi-Nagy, 2013). A mixed-methods approach was used to examine family achievement guilt in relation to measures representing the four dimensions of contextual family therapy theory: facts, transactions, individual psychology, and relational ethics. 121 first-year students from a large, research institution in the Midwest completed a survey examining family achievement guilt (Covarrubias et al., 2020), depressive and anxiety symptoms (Kroenke et al., 2003; 2007) and additional family relationship-oriented variables of interest. Additional variables included relational ethics (Hargrave et. al, 1991), family distance regulation (Draper & Lee, 2001; Levine, Green & Millon, 1986) and attachment (Fraley et al., 2006). Phase one survey results indicated a positive relationship between two domains of relational ethics--trust/justice and entitlement, and family achievement guilt, as well as first-generation status and family achievement guilt, as expected. In addition, depression and anxiety scores were found to be positively related to family achievement guilt and mediated by family achievement guilt in their relationship with trust/justice, entitlement, and first-generation status. Phase two case study analysis added depth to survey results by highlighting themes of family achievement guilt from a focal student perspective and examining them in conjunction with focal student scores on variables of interest. A focal parent interview was also conducted to explore the parent perspective on family achievement guilt. Though additional research is needed to provide a more comprehensive picture of family achievement guilt through a contextual lens, these results provide evidence for addressing family achievement guilt and depression/anxiety symptoms through a contextual lens clinically, as well as making parent-child relationships a focus in interventions at the collegiate level during the adjustment to academia for first-generation college students. [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.]