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This paper aims to report on signs of public awareness and empowerment among the general public that are presumed to determine the viability of the smart contracting (SC) approach and identifies prevailing concerns regarding individual transactional experiences.

A mixed approach was followed to explore perceptions of self-regulation and transaction friendliness by using an interpretative multiple case study method and by presenting a descriptive summative analysis of the data.

On self-regulation, the study reveals spread awareness, empowerment, contractual competences and responsibility. Regarding transaction friendliness, subject matter influences transaction experiences the most, and trust and engagement are the most problematic factors. The findings support the viability of SC, endorsing the application of proactive perspectives in legal and managerial practice.

The study confirms the foundational assumptions of SC, identifies key transactional issues that should be further addressed to improve the functionality of digital trade environments and contributes to the consolidation of the legal design research field on transaction usability.

The findings point to the viability of SC. Organizations and practitioners are given indications on transaction upgrade priorities and invited to adopt and help disseminate the proposal.

The expansion of a collaborative transactional culture can reduce legal disputes, improving the legal environment of business and strengthening private governance regulatory models.

This is the first empirical study on the viability conditions of the SC-approach, identifying transactional usability testing and intervention priorities.