Existing comparative studies suggest Estonia is outperforming many Western European countries in terms of electronic service delivery in the judiciary system. This article provides an explanation for this observation. One crucial element in the explanation is the role of the embeddedness of electronic service delivery in the broader national institutions and subsequent organizational ways of working. In addition, for (digital) innovation it is necessary that there is a certain acceptance of failure, with Estonia having a greater tolerance for failure than The Netherlands. The article also notes that there is arguably a strategic component to the use of benchmarks and comparisons, with compelling stories of frontrunners putting developments in other countries in motion. This may lead to the sometimes confusion situation that Estonia is worldwide successtory, whereas in Estonia itself The Netherlands are occasionally portrayed as a benchmark for digitalisation.