The aim of this research was to compare the level of digital competence of future pedagogical staff (students of pedagogical faculties) in Italy and Poland. The research was conducted using original measurement tools and knowledge tests. The triangulation of techniques and research tools made possible the determination of the level of knowledge of the positive and negative features of the development of the information society, as well as the proficiency and frequency of use of the most popular websites and software. The research was conducted in the first half of 2022 using stratified sampling in both countries (N = 1209, IT = 604, PL = 605). Based on the data collected, it was noted that: (1) Pre-service teachers most often use software such as word processors and presentation creation tools; (2) This group very rarely uses software to create web pages, create visual material, or edit video; (3) The least problematic software that students use are word processors and multimedia presentations; (4) Among the typical ICT mediated activities that cause problems are: searching for and installing freeware (PL), installing and configuring parental control software (PL, IT), creating websites (PL, IT), searching for freely licensed images, and identifying plagiarism (PL); (5) Polish students have more theoretical knowledge about e-risks and the possibilities of the digital world than their Italian counterparts; (6) In most domains, the Italian future teachers rate their competences higher; (7) 53.81% of the respondents in IT and 38.68% in PL received lower results in competence tests, and handling ICT in selected areas causes problems for these students; (8) Both in PL and IT the frequency of ICT use and its seamless integration are predictors for assessing the effectiveness of ICT use in education.