Background and Objectives From the outset of the COVID-19 pandemic, analysts warned that older populations, due to their age, chronic illnesses, and lack of technological facility, would suffer disproportionately from loneliness as they sheltered in place indefinitely. Several studies have recently been published on the impact of COVID-19-related loneliness among older populations, but little has been written about the experiences of already-lonely older individuals; those that had lived with persistent loneliness before the advent of COVID-19. This qualitative study sought to understand how already lonely older individuals navigated and endured the social isolation of the pandemic. Research Design and Methods Twelve semi-structured interviews were conducted with individuals aged 65 or older who scored a 6 or above on the three-item UCLA Loneliness Risk screening tool. Interviews were coded using the constant comparative method. Themes and understandings of loneliness that reoccurred within and across interviews were identified and collected. Results Already-isolated, older interviewees did not necessarily experience the abject loneliness hypothesized by analysts. Most interviewees used long-standing arrangements, in place to mitigate loneliness and endure social isolation, to manage the social deprivation of COVID-19. As a result, their loneliness did not compound during long bouts of mandated social isolation. To the contrary, loneliness during the pandemic appeared to carry a new valence for interviewees, as COVID-19 imbued their isolation with new meaning, rendering their loneliness necessary and responsible. Discussion and Implications Exploring individuals’ subjective perceptions of loneliness can help provide a deeper understanding of what it means to be isolated and alone during COVID-19, and aid in designing strategies to mitigate loneliness.