Freedom Score is an index that reflects the degree of political rights and civil liberties enjoyed by citizens in a given country. It incorporates aspects such as freedom of expression, association, political participation, and the rule of law. In this study, we use the Freedom score as a key contextual variable that may influence how digital development translates into subjective well-being. Happiness Score is a composite indicator derived from citizens’ self-reported life evaluations in the World Happiness Report. It is used as the primary outcome variable to assess overall national well-being from a subjective perspective. Digital Development Index captures a country’s level of digital infrastructure, internet penetration, and technological readiness. It reflects how equipped a nation is to support digital transformation and access to online services. To explore the relationships among these variables, we first selected the relevant indicators (Happiness Score, Digital Development Index, and Freedom score) and removed observations with missing values. Then, we divided countries into four groups based on their Freedom scores using quartiles. This allowed us to compare patterns across varying levels of freedom. We used three types of visualizations: 1. Correlation Plot – This heatmap shows the Pearson correlation coefficients between the three key variables. We find that Happiness Score is positively associated with both Digital Development and Freedom, while the link between Digital Development and Freedom is weaker but still positive. 2. Boxplot of Happiness Across Freedom Groups – This chart reveals that countries in the highest freedom quartile tend to have higher median happiness scores and more concentrated distributions, suggesting both greater well-being and stability under higher freedom levels. 3.Interaction Plot: Digital Development and Happiness by Freedom Group – This scatterplot with trend lines shows how the relationship between digital development and happiness varies by freedom level. In high-freedom countries, the effect of digitalization on happiness appears stronger, with a steeper upward trend. In low-freedom countries, the effect is weaker or flatter. These findings suggest that freedom may amplify the positive effects of digital development on well-being. In other words, digital infrastructure may contribute more to happiness in societies where people are also free to use and benefit from these technologies. Compared to using GDP as the moderator, Freedom captures a different institutional dimension that is more focused on rights and governance. Together, these insights highlight how institutional and technological factors interact to shape human well-being.