This chapter measures compliance with self-regulation whilst mapping out the reasons behind non-compliance. It focuses on a checklist of indicators, the Carta dei Valori (CDV) developed by Forum Terzo Settore (FTS) Lazio in 2015 when threatened by critical public opinion as a result of the Mafia Capitale scandal (2014), and while the Italian Government was drafting the Third-Sector Reform (2014–2017). The CDV requests FTS Lazio member organisations to publish information online to improve their accountability performance from a digital transparency perspective. Relying on a set of both quantitative and qualitative data, this chapter advances a new theoretical module to explain the reasons behind non-compliance with self-regulation. It shows that there are many reasons behind non-compliance, which sometimes are not entirely dependent on an organisation’s commitment to comply with self-regulatory standards. In this context, a distinction between objective and subjective reasons of non-compliance is drawn.