The aim of this paper is to evaluate the usefulness of educational software among teachers in Italy (N = 559). The evaluation of usefulness was conducted on the latest and most popular web-based software used by European teachers, namely: Quizizz, Mentimeter, Wakelet, Padlet, Canva, Emaze, Answergarden, Jamboard, Coggle, Createley, Wordwall, LearningApps, Prezi, Kahoot, Plickers, Trimino, Dobble, Genial.ly, ClassDojo, Explain Everything, KhanAcademy, and Easelly. Based on data collected in the first half of 2022 using an online survey, it was noted that: 1) The majority of teachers are not able to evaluate modern software because they do not use such teaching resources as those listed; 2) About 9.3% of teachers rate the listed software highly; 3) Most commonly teachers use and also rate highly: Canva, Wordwall, Padlet, LearningApps, Kahoot, Coggle, Jamboard, and Prezi; 4) Seniority and workplace does not always differentiate the evaluation of educational software.