This study focuses on students' self-assessment during their learning process related to computer programming concepts, taking into account challenges and obstacles both teachers and students face, with the aim to contribute to the development of guiding principles and practices and enhance the teaching process of computer programming in primary education. This is a research area that, to the best of our knowledge, has not been fully investigated, especially in Greek schools, and its originality lies in the application of an integrated approach, which combines the analysis, correlation and triangulation of data from both bibliographic and pilot studies sources. By including data from interviews, questionnaires, researchers' diaries and field notes from two three-week pilot studies with third-grade students, this study addresses the deficiencies of prior research. Past studies rely on limited data sources, such as single-method approaches and small sample sizes, leaving out broader contexts or specific educational settings, such as Greek schools. This study's comprehensive approach offers a more detailed and nuanced understanding of the research problem. The focal point of the research questions in this study, is to identify elements that provide important findings concerning: (a) the enhancement of students' skills alongside the identification of obstacles they may face during their self-assessment process, (b) teachers' challenges during incorporation of modern educational tools in the learning process and (c) the attitude of teachers as well as the role they play in the students' self-evaluation process. Findings of this work serve as an essential tool for students, teachers and researchers, facilitating continual improvements in the educational process and students' programming experience through sharing their experiences, exchanging ideas and proposing possible solutions to the challenges that arise. The research findings generate recommendations for educational authorities, including the Greek Ministry of Education and the Institute of Educational Policy, aiming to enhance the Primary school curriculum.