Throughout time, type design methods have changed in response to the limitations of various print technologies. In today’s world where digital technologies dominate people’s lives and audiences are more inclined to read on digital devices, every language is trying to publish its information both online and in mobile applications. In accordance with these new needs and limitations, designers began to draw outlines compatible with the pixel-based environment of screens in order to maintain the readability and beauty of letters. Despite the advent of web fonts and the production of new fonts compatible with the web environment in the Persian language, many browsers still use Tahoma and Segoe UI Arabic as a default standard and accepted font families. From the Persian type designer’s perspective, the design of these fonts has not followed the structural and aesthetic principles of the Arabic script. To identify the issues in both fonts, a comparative method is used to compare four important fundamentals of the Naskh style: principle, proportion, baseline, and composition with the structure of Tahoma and Segoe UI. The results show that Tahoma and Segoe Arabic have been following the geometry of Latin letters, which took away their identity and beauty. Accordingly, the design decisions undertaken in these fonts are the result of their designers’ lack of knowledge on the structure of the Arabic script. However, the successful web fonts designed by Persian-speaking designers have proven that the structure of Arabic letters can be well-adapted to the arrangement of pixel-based environments.