Background and Objectives While research on loneliness in later life has increased during the COVID-19 pandemic, we still lack diverse qualitative approaches capturing lived experiences of lonely older adults. Approaches to research with older adults instead of on them are also scant in gerontological literature on loneliness. Through solicited diaries, this study aimed to explore how older Australians who were already lonely before the pandemic managed lockdowns (stay-at-home orders) in Victoria, Australia, which lived through one of the longest lockdowns in the world. Research Design and Methods This article is based on qualitative diaries completed by 32 older adults (aged 65+). Diaries provide a ‘live’ document where participants become active research partners, recording and sharing their perceptions and experiences. This method is useful to capture sensitive issues, but to our knowledge has not been employed in loneliness studies. Data were thematically analyzed through identification of themes within and across diaries. Results Loneliness was defined by participants as a detrimental absence of companionship and meaningful social interactions. For most, lockdowns exacerbated loneliness, presented new triggers, and upended coping strategies. The disruption of the ‘emotion work’ involved with managing loneliness led to a reconfiguration of response strategies, including through digital technology, which brought both challenges (e.g., digital ageism) and opportunities (e.g., novel communication forms). Discussion and Implications Understanding how older people living alone define and respond to loneliness in diverse contexts – for example, before and during a pandemic that restricted social interaction – provides critical insights to inform interventions to tackle loneliness.