Afghanistan has experienced more than four decades of severe disruption, ever since the communist coup of April 1978 plunged the country into a state of disorder that was then severely aggravated by the Soviet invasion of Afghanistan in December 1979. Despite the high hopes that accompanied the overthrow of the Taliban regime in 2001, Afghanistan’s path in the first two decades of the 21st century has proved to be anything but smooth, and this article highlights a confluence of challenges – political, diplomatic, and societal – that Afghanistan presently faces, challenges that in large measure account for the profound uncertainty that clouds its future. The article is divided into four sections. The first provides some context for the discussion of these three challenges. The remaining sections investigate the particular challenges – intra-elite rivalries, a fragile and defective peace process, and the underreported but grave threat to life and limb in Afghanistan resulting from the COVID-19 pandemic – in more detail. Together, these challenges highlight the dangers of wishful thinking about harsh realities.