We present a qualitative interview study that examines what happens when things do not go as planned with digital contraception. Through an analysis of 27 interviews with ongoing users of digital contraception at the time of the study, we convey participants' accounts of their experiences regarding unplanned pregnancies or use of emergency contraception to avoid an unplanned pregnancy. Our analysis considers participants' sense-making processes, and notably how they attended to questions of risk and responsibility. Finally, we depict how these participants came to continue using digital contraception after these experiences. Our study connects to ongoing conversations on technological failures in personal informatics and safety-critical systems. We emphasise that failure and success should not be used as a binary classification of long-term users' relationships with self-tracking technology, which are intimate and critical. Rather, the sustained relation with an intimate technology is composed by several failures' which are interpreted, acted upon, and, ultimately, overcome.