This research paper explores the evolution and challenges of cross-border electronic contracts (e-contracts), highlighting their significance in modern international trade. As digital globalization transforms commercial transactions, e-contracts have emerged as vital tools for facilitating efficient and seamless cross-border dealings. However, their widespread adoption is accompanied by multifaceted challenges. The paper examines legal obstacles, including disparities across jurisdictions and issues surrounding the enforceability of e-contracts, drawing attention to the efforts of international bodies like UNCITRAL to mitigate these through harmonized legal frameworks. Technical challenges such as security, authentication, and interoperability are analyzed, alongside practical difficulties like cultural and linguistic barriers that impact the negotiation and execution of e-contracts. The study also investigates emerging technologies like blockchain and smart contracts for their potential to address some existing challenges, and underscores the role of Online Dispute Resolution (ODR) mechanisms in resolving disputes. This analysis aims to shed light on the complexities of cross-border e-contracts, offering insights for policymakers, legal practitioners, and businesses, while suggesting future research directions for navigating these challenges effectively.