The human social system is facing complex social issues and (new) initiatives coming from different social actors are born to try to tackle these complex social issues. Social innovation is the field where these initiatives function, so it is also a complex field to identify and frame. Thus a new theory, the Transformative Social Innovation Theory (TSI), was developed in order to frame and bring more clarification on the social innovation field to contribute to societal transition and transformation. The five TSI tools were developed from the TSI theory and they are training tools. All the TSI tools aim to (dis)empower the social innovation initiatives, actors and networks in the process of transformative social innovation. Transformative Social Innovation is the process of changes in social relations involving challenging, altering and/or replacing dominant institutions and structures which are considered to be the roots of systemic errors. This study sought to explore the Transformative Social Innovation tools from the perspective of the Strategic Sustainable Development (SSD). In this regard, the Framework for Strategic Sustainable Development (FSSD) was adopted as it provides a principle-based and scientifically-proved definition of sustainability as well as a systems thinking approach regarding the complexity of global sustainability challenges. This research project tried to identify the potential contributions of the TSI tools to sustainability and the entry points of the tools where relevant SSD features could complement them so that they can contribute to strategically move the society towards sustainability. A qualitative research approach was selected. The methodology included four research methods, namely document content analysis, interviews, the FSSD analysis and prototyping. The results of this research indicated three main contributions of the TSI tools that could help to strategically move the society towards sustainability. Five entry points where the tools could be complemented with SSD features and a set of add-ins from SSD that could complement the current TSI tools were identified. The add-ins were sent to the TSI theory authors for the expert consultation.