The authors examine the roles of social connectedness in mediating the relation between the loss of loved ones and life satisfaction in older residents living in a retirement community. Data were collected through a mail survey on a random sample of 734 older residents (M age = 67 years, SD = 9.6 years) in a retirement community in the Southwest. Analyses were conducted using SPSS macros for estimating the indirect effects through multiple mediators. Participants who experienced the loss of loved ones in life reported statistically significantly higher life dissatisfaction scores than those who reported no such loss. The effects of loss on perceived life dissatisfaction were partially mediated by individual connectedness and satisfaction with received social support but not by support network size or collective connectedness. Interventions with older adults who experienced loss in life need to help alleviate their loneliness and increase their satisfaction with social support.