Turkmenistan is slowly emerging from decades of darkness. President Gurbanguli Berdymukhamedov has vowed to modernize the country by encouraging the uptake of new technology for economic development and more efficient governance. Hundreds of thousands of Turkmen citizens are now online. However, the country faces serious challenges as it prepares to go digital. Infrastructure is primitive, and public access is fully controlled by a stateowned monopoly. Slow speeds, exorbitant pricing, and technological illiteracy all constitute major hurdles. Authorities are moving to address the capacity problem, but Turkmenistan's repressive regime is unlikely to relinquish its stranglehold on cyberspace access and content. All media -- including the internet -- are closely controlled. State censorship and surveillance are significant, as are intimidation tactics that encourage user self-censorship. This study highlights the ambivalent policies and practices that have left Turkmenistan mired in the digital doldrums, torn between its desire to join the worldwide web and its compulsion to control cyberspace.