National System of Transactions Monitoring of Executive Organizations is one of the electronic monitoring systems of General Inspection Organization (GIO), which this organization has been faced with some kinds of problems and successes on its deployment path. It is clear that the detection of these obstacles and constraints can enhance the electronic monitoring efforts in all over the country. Therefore, this research aims to leverage a case study in South Khorasan province to do pathology and eliminate the socio-cultural barriers of this system. So we used a combinational research method (qualitative and quantitative). It means we initially developed a qualitative conceptual model based on a broad literature review, and using Delphi technique. Based on this model, 9 hypotheses related to socio-cultural obstacles and constraints of electronic monitoring systems were designed. These hypotheses were assessed quantitatively by designing and running two questionnaires and interviews with managers and experts of General Inspection and executive organizations of province and consequently, 5 cases of them were proved. The research results show that the main socio-cultural constraints of the mentioned e-monitoring system includes the belief on solemnity in user interface design, users> satisfaction ignorance, staff enforcement to use system, the risk of lessening responsiveness and responsibility of executive staff, and the diversity and inconsistency of mentioned staffs behavior and culture. Finally, our suggestions to overcome the current obstacles were discussed and the future research opportunities were proposed.