Background: The digitalization and integration of data are increasingly relevant for hospitals. Several methods exist to assess and structurally develop digital maturity. However, it is notable that German hospitals lag behind the European average with respect to digitalization. Objective: We hypothesized that: (a) the perspective of hospital managing directors regarding the state of digitalization in German hospitals plays an important role in the investigation of barriers, and (b) the Hospital Future Act in 2020 may help to surmount those barriers. Methods: Aligned with the Checklist for Reporting Results of Internet E-Surveys (CHERRIES), two online surveys were conducted, one in 2019 and one in 2021. Results: The first study covered 184/344 hospitals and the second, 83/344. The responsibility for deciding on the implementation of digitalization lay with the management (115/184; 62.5%). About 54.9% (101/184) of the managing directors desired digitally supported workflows, together with employees or users. In total, 74.7% (62/83) of hospital managing directors expressed an increase in digitization compared to 2019, with a percentage increase of 25.4% (SD 14.41). In some cases, we analyzed the data using an ANOVA, chi-squared test and Pearson’s correlation, but there was no significant relation identified among the variables. Conclusions: This online-based survey study demonstrated that the development of a digitalization strategy is still strongly tied to or dominated by the attitude of the management. One could assume a lack of acceptance among employees, which should be surveyed in future research. The Hospital Future Act, as well as the COVID-19 pandemic, has positively influenced the digital maturity of hospitals.