Discussing the legal doubts in the context of Iranian law shows that there are a number of legal uncertainties in the Iranian legal system hindering, or at least putting in doubt, the development of electronic commerce in both national and cross-border electronic transactions. Despite the fact that some of them have been addressed by the Iranian Electronic Commerce Act 2004 indirectly, however a detailed legal work is still definitely needed to elaborate the questions and provide solutions developing and modernizing Iranian law in the context of electronic contracts. The author in the current work tries to analyse the questions by a horizontal comparative study of the UNCITRAL Model Laws, the Convention on the Use of Electronic Communications in International Contracts 2005, the EU law, English law, American law and Iranian law. Also, a three-stage roadmap that acts as the guiding principle of this research is employed to develop the Iranian legal system in the context of e-commerce. The first stage focuses on whether the exact application of Iranian traditional law or its expansion can address the emerging legal doubts; the second introduces legal presumptions or rules; and the third theorizes new rules. The research concludes that the Iranian legal system may be modernized and developed in the context of electronic contracts by adopting the legal policy and solutions of other legal systems by both scholarly legal doctrines and legislation.