Five years of experimenting with Personal Health Records has not yielded the results that big companies like Google and Microsoft expected. Whereas Google pulled the plug on its product offering, Microsoft struggles to reach sufficient critical mass. This study adopts a user perspective (51 interviews) in conjunction with grounded theory, to offer explanations why Google Health failed and predictions relative to Microsoft's ability to reach a tipping point with respect to product/service viability. Noteworthy, vendors ignore relevance, or perceived usefulness when designing PHRs. Moreover, low trust and high risks do not bode well for long-term success, with the widely used information systems success models often neglecting the latter two critical dimensions.