Hope serves as an overarching concept for a range of engagements that demonstrate the benefits of a positive outlook for coping with chronic conditions of ill-health and disability. A dominant engagement through medicine has positioned hope as a desirable attribute and its opposite, hopelessness, as pathological. In this engagement hope is individual, internally located and largely cognitive and able to be learned. Attaining hope reflects a process of coming to terms with the losses associated with long-term conditions and of imagining new meanings and purposes for the future ahead. This process is characterised by a set of linear temporal stages, from loss and denial to acceptance and reappraising the life-course, by an emphasis on the morally desirable exercise of self-care and by a desired outcome that, in the absence of cure, is hope. Through interviews, we aim to unsettle the privileged status given to a positive outlook through examining the expressions, contexts and negotiations of hopelessness of people living with multiple conditions of ill-health and/or disability. These narratives of hopelessness disclose the ways in which realistic imagined possibilities for the future are constrained by external structures of time and function that demand complex negotiations with places, bodies and other people. As a situated and relational narrative, hopelessness draws our attention to the need to rebalance the exclusive attention to individual, internal resources with a renewed attention to contexts and settings. Moreover, hopelessness can be generative for those living with multiple conditions in shaping alternatively framed priorities with respect to their temporal and interpersonal relations.