Web Archiving in the National Library of Singapore is one of the fundamental actions to ensure the preservation of national digital heritage. By the year 2006, the National Library of Singapore (NLS) has started a Web Archive initiative called Web Archive Singapore (WAS). This paper analyses the legal and technical issues that act as obstacles for the collection and management of the digital collections established through Web Archiving in Singapore. WAS lacks an adequate copyright framework for its digital records management, including long-term preservation and access. From a technical perspective we analyze the latest international developments and challenges of web archival. In both analysis legal and technical, we emphasizes on users of archives as the main leitmotif when focus on solutions. Our final recommendations and conclusions are underlined by the fact that NLS must encourage research and knowledge creation through the support of digital humanities, implementing technical and legal solutions that foster a Web Archive.