In a period strongly marked by constraints and abrupt societal changes, school leaders had to manage the pandemic crisis, guide changes, and find new solutions to respond to the demands of increasingly digitalised schools. Taking this situation into consideration, a study was carried out with the aim of identifying the main challenges faced by school leaders in Portugal related to the teaching and learning processes, platforms and other digital technologies (PDT) used, and lessons learned for a post-pandemic future. From the methodological point of view, a questionnaire with closed questions on digital technologies and open questions on the COVID-19 pandemic issue was submitted to Portuguese school leaders in the period between November 2020 and March 2021. The results, based on a descriptive statistical analysis of the closed questions and the content analysis of the open answers of 145 school leaders, point to aspects related to lack of training, lack of resources, widening inequalities and communication issues. The PDT are the same as used before, mainly office applications, and spaces for storing and sharing school information; however, these PDT were used more frequently. These findings imply the need to invest in continuous training for leaders in how to manage crises and how to optimise the use of PDT in schools; and to capitalise on internal and external partnerships in collaborative efforts and networking to overcome the lack of resources, social needs and inequalities. The lessons learned during the process of finding and evaluating solutions can contribute to improving school management processes in crisis situations.