The Internet has played important roles in driving political changes around the world. Why does it help to topple political regimes in some places but improve the quality of governance in others? We found Internet usage in general leads to citizens’ distrust in political institutions. Different political environments, however, can condition such trust-eroding impacts of the Internet in significantly different ways. A democracy enables citizens to connect their online behaviors and offline expression and organization, releasing political discontent while facilitating state–society communication. On the contrary, by restricting various forms of off-line expression, authoritarian regimes drive Internet-active citizens' discontent and distrust to higher levels. We use the World Values Survey data to establish these different mechanisms across democracies and authoritarian systems. Entropy balancing shows our findings to be highly robust.