Using cross-country data, this note explores the potential impact of selected digital technologies on tax collection and compliance. The analysis makes use of multi-dimensional International Survey on Revenue Administration, Tax Administration Diagnostic Assessment Tool, and Revenue Administration-Gap Analysis Program (RA-GAP) data with results indicating that digital technologies could help enhance tax collection, but with effects that vary by the type of specific digital service or tools introduced. While the results demonstrate a strong association between digital tax administration operations and improved performance outcomes, the realization of revenue gains is heavily contingent on accompanying policy, legislative, and administrative reforms, as well as the availability of adequate digital connectivity and capable tax administration staff. The cross-country approach provides reasonable upper-bound estimates on revenue gains, which, however, need to be carefully validated with country-specific case studies. The note reviews single country case studies from selected micro-economic literature that complement the cross-country results and reveal key enabling factors necessary to reap and sustain the benefits of new digital investments.