Purpose: Unmet support needs are prevalent in men affected by prostate cancer. Moreover, little is known about the optimal type of social support, or its mechanism effect between coping and emotional outcome in men affected by this disease to identify areas for clinical intervention. This study aimed to empirically test the propositions of social support theory in "real time" within individual men living with and beyond prostate cancer. Methods: Purposeful sub-sample from a larger prospective longitudinal study of prostate cancer survivors, took part in real time data collection using mobile technology. Self-reports were collected for 31 days prompted by an audio alarm 3 times per day (a total of 93 data entries) for each of the 12 case studies. Electronic data were analysed using time series analysis. Results: Majority of response rates were >90%. Men reported a lack of satisfaction with their support over time. Testing the propositions of social support theory "within individuals" over time demonstrated different results for main effect, moderation and mediation pathways that linked coping and social support to emotional outcome. For two men, negative effects of social support were identified. For six men the propositions of social support theory did not hold considering their within-person data. Conclusion: This innovative study is one of the first, to demonstrate the acceptability of e-health technology in an ageing population of men affected by prostate cancer. Collectively, the case series provided mixed support for the propositions of social support theory, and demonstrates that "one size does not fit all".