The Digital Education Action Plan (2021–2027) launched by the European Commission aims to revolutionize education systems, prioritizing the development of a robust digital education ecosystem and the enhancement of teachers’ digital transformation skills. This study focuses on Universidade Aberta, Portugal, to identify the strengths and weaknesses of teachers’ digital skills within the Digital Competence Framework for Educators (DigCompEdu). Using a quantitative approach, the research utilized the DigCompEdu CheckIn self-assessment questionnaire, validated for the Portuguese population, to evaluate teachers’ perceptions of their digital competences. A total of 118 teachers participated in the assessment. Findings revealed that the teachers exhibited a notably high overall level of digital competence, positioned at the intersection of B2 (Expert) and C1 (Leader) on the DigCompEdu scale. However, specific areas for improvement were identified, particularly in Digital Technologies Resources and Assessment, the core pedagogical components of DigCompEdu, which displayed comparatively lower proficiency levels. To ensure continuous progress and alignment with the Digital Education Action Plan’s strategic priorities, targeted teacher training initiatives should focus on enhancing competences related to Digital Technologies Resources and Assessment.