Following the development track of so called second-generation internet, legal issues concerning electronic contract also evolve. It seems necessary to extend from the hypothetical study and the electronic trade issues of early stage to the new frontier, especially the challenges derived from the enactment of Electronic Signature Act and the application of contemporary Civil Law. While it is true that the academic review may indicate to us various electronic commerce related legal articles in Taiwan, new issues concerning the application of Electronic Signature Act, which is taken as the foundation for conducting an electronic contract, should be added. Further, it also becomes unavoidable to include the issues that are commingled with both the Electronic Signature Act and Civil Law, for the incompleteness of the Act in covering all the electronic contract related problems. For instances, the relationship between article 3 of the Civil Law and article 9 of the Act in determining the identity of contracting parties; the applicability of agency rules of Civil Law in computerized electronic agent; the applicability of traditional concept of subject matter illustrated under Civil Law in governing the digital merchandise; and the relationship between article 95 of Civil Law and article 7 of the Act in determining the revocability of a non-oral presentation as well as the enforceability of said presentation. For others, the attribution of electronic information among parties and the legal definition of “reconfirm” are similarly deserves our special notice. Basing upon the basic rules governing the civil contract, it’s been this paper’s ideology to follow the pace of norm development model for internet. This paper tried to examine on the challenges that our electronic contract system faced, in line with related international developments. Further, this paper looked into the new issues derived from the enactment of our Electronic Signature Act as well as their differences with international or American development. Finally, the paper reexamined the related contract rules of our Civil Code and proposed a recommendation for our future amendment.