As part of Vision 2030, the Kingdom of Saudi Arabia (KSA) has begun implementing broad economic and legal reforms to improve its tax environment and create an amicable setting for international investors. However, there are challenges to this endeavour, which are not limited to Saudi rules. Digitalization is one such challenge in income taxation at the global level. This study investigates the challenges in taxation arising from digitalization that can potentially affect base erosion and profit shifting (BEPS) mechanisms both internationally and in Saudi Arabia. One major problem in the Saudi tax judiciary is the interpretation of international tax treaties to determine the existence of a permanent establishment (PE) for the purpose of Saudi income tax for a non-resident providing remote services within Saudi territory. By examining contradictory decisions related to two typical digital services, namely online travel companies (OTCs) and international telecommunication, this study highlights the complexity involved in digitalization, withholding tax, and PE. By analysing Saudi practices against the context of international rules, this research also highlights the need to clearly define the meaning of a ‘permanent digital establishment’. Finally, it underscores the necessity of establishing a permanent higher chamber in the tax judiciary, which will make decisions on stable judicial tax principles. This will improve the Saudi legal tax environment and ensure its consistency with international practices.