The aim of the present study was to provide an inclusive and realistic account of the offense processes of naturally occurring, sexually exploitative interactions between offenders and victims that took place via Internet communication platforms, and develop an offense process diagram of online sexual grooming and abuse. Five case series, comprising 29 transcripts of 22 interactions, were analyzed using the qualitative approach of thematic analysis. Police reports were reviewed for descriptive and case-specific information. The five offenders were men aged between 27 and 52 years (M = 33.6, SD = 5.6), and the number of children they communicated with ranged from one to 12 (M = 4.6, SD = 4.5). Victims were aged between 11 and 15 (M = 13.0, SD = 1.2), and were both female (n = 17) and male (n = 6). Findings revealed that offenders employed either an indirect or a direct approach to conversations with victims and initiating contact with them. The approach offenders employed was also reflected in the types of strategies they used. Only two offenders were found to engage in aspects of sexual grooming as part of an indirect approach; the majority of the interactions by the other three offenders, that lacked features of sexual grooming altogether, were found to be of a direct approach. These findings are discussed in relation to current issues surrounding terminology and definition of sexual grooming, as well as theoretical and practical implications, concluding with suggestions for future research.