The family environment is critical in supporting healthy adolescent development. Following thernopening of technical and preparatory schools in Ethiopia, it has become necessary for studentsrnparticularly of the rural areas to move to the nearby towns for the duration of their training.rnHowever, whether adolescents who come from rural areas (who might lack consistent adultrnsupervision and exposed to a relatively new environment) are having an elevated sexual-riskrntaking behavior and more psychosocial problems remain unanswered.rnIn an attempt to respond to questions posed on these differential vulnerabilities of adolescents, arncomparative cross-sectional study that examined the effect of living arrangement and parent-teenrnconnectedness on sexual risk behaviors and psychosocial problems of students was conducted inrnDessie preparatory school, Ethiopia. A sample of 667 students (512 male and 155 female)rncompleted a pre-tested structured anonymous questionnaire. Qualitative information wasrnobtained from four focus group discussions and sixteen peer-to-peer interviews segregated byrngender and residence.rnWe found that living with friends (OR=2.77; 95%CI=1.47, 5.24), alcohol consumptionrn(OR=1.94; 95%CI =1.24, 3.04), lower perceived family connectednessrn(OR=0.97; 95%CI=0.95, 0.99) and parental monitoring (OR=1.70; 95%CI=1.06, 2.73), older agern(OR=4.37; 95%CI=2.11, 9.04), having peer pressure (OR=1.82; 95%CI=1.20, 2.77) and peersrnwho are sexually experienced were associated with increased odds of sexual activity.rnHaving a depressive symptom was associated with female gender (OR=1.96; 95%CI=1.18, 3.23)rn, lower family connectedness (OR=0.96; 95%CI=0.94, 0.99), lower grade-pointaveragern(OR=1.93; 95%CI=1.01, 3.71), and living with friends (OR=3.16; 95%CI=1.66,rn5.00), relatives (OR=2.52; 95%CI=1.28, 4.95) or alone (OR=2.15; 95%CI=1.04, 4.46).rnThe study revealed that suicide attempt in the past 12 months was linked to having arnhistory of suicide attempt in the family (OR=2.59; 95%CI=1.09, 6.15) or among friendsrn(OR=4.32; 95%CI=1.88, 9.94), female gender (OR=2.60; 95%CI=1.05, 6.48) and sexualrnactivity (OR=3.00; 95%CI=1.27, 7.11).rnviiirnThe overall research finding indicate that living with both biological parents and good parentteenrnconnectedness are related to better psychosocial health and being sexually abstinent.rnThe evidence from this study suggests that parents need to know the continued importance ofrnhaving good relationship with their adolescents. Youth programs should also address the centralrnrole of familial influences (specifically high levels of parental connectedness and monitoring) inrnprotecting boys and girls from unsafe sexual behavior and psychosocial problems. Additionalrnresearch needs to explore the impact of familial influences on adolescent reproductive andrnpsychosocial health and preferably use longitudinal designs to determine the stability of thernobserved association over time.rnKey words: Adolescents, living Arrangements, parental attachment, sexual risk behaviorsrnpsychosocial problems, Ethiopia.