Singapore's technological prowess as one of the most networked city, society and nation is reflected in most statistical data. Indeed, Singapore is relentless in its pursuit of making technological and Internet history/ies. In its latest Intelligent Nation 2015 (iN2015) master plan, Singapore plans to integrate all aspects of info-communications into a single ultra-fast broadband platform that will be capable of delivering ultra-fast Internet. This paper provides a brief update on the extent of technological and Internet deployment. More importantly, it looks at how the Internet has further developed by analysing the events surrounding the 2006 General Elections in Singapore. Each election in Singapore is arguably a key regulatory milestone for the Internet because new rules are either invoked via new or revised legislation or new warnings issued to keep a lid on the effectiveness of new technologies. While Singapore has undoubtedly made 'history' in its regulatory approaches and strategies in managing the liberatory impulses, with outright censorship of racial, religious and pornographic -and, since 11 September 2001 (9/11), terrorist-related -websites making headlines around the world, it has also been able to score impressively in the technological competencies of its citizens. In the discussion that follows, we examine the current state of the Singaporean blogosphere and considers if the regulatory landscape has been altered following pressures brought about by blogs and other alternative websites. It argues that the implementation of both overt and subtle controls of alternative political websites as well as heavy-handed actions by the authorities to rein in on errant Internet users and bloggers, along with the occasional talking-down of the significance of the Singaporean blogosphere, have accentuated the ambivalence that the Internet in Singapore has (re)presented.