The COVID-19 pandemic had a significant impact around the world and has drastically changed the field of education. In addition to instructional materials, new technologies enabled access to new learning environments. However, the COVID-19 pandemic has highlighted some significant disparities between conventional information and communication technologies (ICTs) included in teacher training curricula in Greece and the new software required for remote learning and teaching. Thus, the study presented here aimed to examine the mobilisation of in-service teachers and their readiness to address teaching challenges while delivering online lessons. Online questionnaires were distributed to 110 in-service preschool teachers. The study aimed to answer four research questions about teachers' ICT knowledge and the ways in which they used technology for work purposes, as well as the difficulties they encountered while teaching online. Evaluation of the data resulted in three main findings: (1) holding an ICT training certificate did not have a significant impact on the implementation of new technologies in distance education; (2) support from local education authorities was an important factor of the transition to online teaching; and (3) Greek teachers did not feel fully prepared to teach online.