Online self-disclosure is perhaps one of the last decade's most studied communication processes, thanks to the introduction of Online Social Networks (OSNs) like Facebook. Self-disclosure research has contributed significantly to the design of preventative nudges seeking to support and guide users when revealing private information in OSNs. Still, assessing the effectiveness of these solutions is often challenging since changing or modifying the choice architecture of OSN platforms is practically unfeasible. In turn, the effectiveness of numerous nudging designs is supported primarily by self-reported data instead of actual behavioral information. This work presents ENAGRAM, an app for evaluating preventative nudges, and reports the first results of an empirical study conducted with it. Such a study aims to showcase how the app (and the data collected with it) can be leveraged to assess the effectiveness of a particular nudging approach. We used ENAGRAM as a vehicle to test a risk-based strategy for nudging the self-disclosure decisions of Instagram users. For this, we created two variations of the same nudge and tested it in a between-subjects experimental setting. Study participants (N=22) were recruited via Prolific and asked to use the app regularly for 7 days. An online survey was distributed at the end of the experiment to measure some privacy-related constructs. From the data collected with ENAGRAM, we observed lower (though non-significant) self-disclosure levels when applying risk-based interventions. The constructs measured with the survey were not significant either, except for participants' External Information Privacy Concerns. Our results suggest that (i) ENAGRAM is a suitable alternative for conducting longitudinal experiments in a privacy-friendly way, and (ii) it provides a flexible framework for the evaluation of a broad spectrum of nudging solutions.