Online contracting has witnessed some remarkable developments since the internet became a tool for commerce. Mainly in Iraq, such increased practices of online contracting in the cross-border context have not been accompanied with a parallel development in the law. Against this background, this thesis argues that certain rules found in contracting theory and conflict of laws, especially in the Iraqi law, are not adequate enough to govern the legal obligations and disputes arising out of concluding online contracts on websites. A comparative analysis of the legal systems in three different jurisdictions will be used to consider the issues in this thesis: the EU, the US, and Iraq. The rationale behind choosing the aforementioned jurisdictions was to evaluate how successfully each of these jurisdictions have been in dealing with online contracting cases and disputes. Furthermore, the ultimate goal is to examine the possibility of adopting the harmonised laws of the EU and the courts-based approach of the US in proposing a proper reform of Iraqi law in the context of jurisdiction and applicable law matters. In the EU, although substantial harmonisation of rules has been implemented by the European legislature to ensure an effective application of the rules governing contractual obligations in both offline and online practices, some rules are still questionable in terms of their application to internet activities. In the US, despite the fact that courts have been challenged by an abundant number of online contracting cases, the application of US personal jurisdiction rules and the validity and enforceability of online choice of court and law agreements remain unsettled. In Iraq, the application of certain rules of traditional conflict of laws is outdated and the rules are not fit to govern the disputes arising out of online contracts concluded on websites. This thesis concludes that certain reforms of the law, especially Iraqi law, should be more realistic, feasible and appropriate for governing the online contracting process rather than proposing new specific rules for on-line transactions. More specifically, Iraqi legislature should pay more attention to update the Electronic Signature and Transactions Act (IESTA) to provide more legal certainty for contracts concluded on websites. Furthermore, jurisdiction and applicable law rules laid down in articles 14, 15 and 25 of the Civil Code should be also reformed taking into account the special characteristics of the contracting process over the internet.