This study aimed to examine the opinions of Montessori educators on the digital assessment tool they use in terms of 21st-century teacher skills. The study sample covered 14 Montessori educators working in early childhood classes in public and private preschool educational institutions, located in Barcelona and Istanbul, where the Montessori educational approach is applied. In the study, the experiences of the Montessori educators with the digital assessment tool they use as the assessment tool were examined in terms of the identified 21stcentury teacher skills. To this end, the research was designed with a phenomenological approach in the qualitative research method. The data were obtained through the personal information form and structured interview questions prepared for the digital assessment tool used by the Montessori educators. In the analysis of this data, the phenomenological study of Moustakas (1994) was introduced through the steps of the analysis. The perspectives of the Montessori educators concerning digital assessment, their application experiences regarding the digital assessment tool, and their views on their experiences were discussed in terms of utilization of the digital tool applications, as well as to use and evaluate information, their skills regarding collaborative work and communication, and finally their communication skills with the parents, which are among the 21st-century teacher skills. It was concluded that different factors influenced the opinions of the Montessori educators, where there were positive and negative expressions within the scope of these skills regarding the digital assessment tool.