How can tax administrations address ambiguity and information frictions in increasingly complex tax systems? This paper examines the compliance effects of introducing a digital Many-to-Many Communication (MTMC) service, a tax assistance intervention through which tax officials respond to taxpayers’ queries in a credible, transparent, and real-time manner. It provides evidence on both the shortand long-run impacts of the MTMC system on tax compliance along the extensive margin. Exposure to a digital tax assistance scheme improves tax filing compliance through the reduced informational friction channel. However, it also provides evidence, consistent with theoretical predictions, that direct revenues remain modest, suggesting that assisted taxpayers did not change their perceived probability of detection and thus reported little to no income. The MTMC intervention also generated indirect benefits in local networks. Tax information spills over local social networks and generates more compliance along the extensive margin, among unassisted taxpayers. These findings shed new light on the potential of real-time communication tools to strengthen compliance with taxes. More importantly, they raise awareness of the potential importance of combined strategies that facilitate tax filing while deterring underreporting.