In this symposium talk, we will draw on insights from our qualitative research and digital ethnography study, DELVE, to explore the ways individuals experiencing self-harm and suicidal feelings engage online over a 6-month period. We recruited 14 participants to this study, conducting one-to-one interviews with them at baseline, 3-month, and 6-month timepoints. In between interviews participants were asked to complete a daily structured diary which collected data on their online and offline behaviours, mood changes, and any significant life events. Our trajectory analysis of this data took a novel approach to examining the lived experiences of users, revealing shifts in their emotions and behaviours over time, and the underlying reasons for these changes. We also used thematic analysis to capture user perspectives on moderation and moderators in self-harm and suicide online spaces. Our findings highlighted the importance of a balance between cognitive flexibility - the capacity to adapt behaviour and consider different perspectives - and cognitive rigidity - the tendency to stick to established behaviours and thought patterns - amongst individuals engaging with self-harm/suicide content online. We recommend the development of tailored interventions that integrate metacognition and digital literacy skills, such as our diary template, empowering users to have greater control online during periods of cognitive flexibility. Additionally, we recognise the pivotal role of online industry leaders and policymakers in developing effective moderation procedures, and we provide practical recommendations for keeping vulnerable users safe.