This study identifies specific social and functional disadvantages associated with living alone during old age in Sweden and assesses whether these associations have changed during recent decades. Data came from repeated cross-sectional surveys of Swedish adults aged 77+ during 1992–2014. Findings indicate that several types of disadvantage are consistently associated with the probability of living alone including financial insecurity and having never married for women and having never married and mobility impairment for men. Also for older men, low education has become an increasing strong determinant of living alone. These findings suggest that older adults who live alone are a subgroup that is particularly, and in some cases increasingly, vulnerable with respect to social and functional status. This has important policy implications related to addressing the needs of this growing subgroup as well as methodological implications for studies on the health effects of living alone.