Background: The quantification of diabetes-related quality of life (DR-QoL) is an essential step in making Type 2 Diabetes (T2DM) self-management arrangements. The European General Practitioners Research Network (EGPRN) initiated the EUROBSTACLE study to develop a broadly conceptualised DR-QoL instrument for diverse cultural and ethnic groups; high and low-income countries. In 2016 the Diabetes Obstacles Questionnaire-30 (DOQ-30) was introduced. Objectives: The research aimed to study obstacles a patient with diabetes (PWD) may face in everyday life. First, we assessed how descriptive and clinical characteristics and the residential country were associated with the obstacles. Secondly, we calculated the proportion of respondents who expressed obstacles. Methods: Data were collected in 2009 in a cross-sectional survey in Belgium, France, Estonia, Serbia, Slovenia, and Turkey. Multiple linear regressions were computed to detect associations between descriptive and clinical characteristics, residential country, and obstacles. Percentages of respondents who perceived obstacles were calculated. Results: We found that although descriptive and clinical characteristics varied to quite a great extent, they were weakly associated with the perception of obstacles. The residential country was most often associated with the existence of some obstacle. The highest percent (48%) of all respondents perceived ‘Uncertainty about Insulin Use’ as an obstacle. Conclusion: Descriptive and clinical characteristics were weakly associated with perceived obstacles. However, the residential country plays an essential role in the decline of the QoL of PWDs. Education of both PWDs and healthcare professionals (HCPs) plays an essential role in countering the fear of insulin.