What is one of the world's most prominent advocates of Internet freedom doing in a country where unregulated access to information is generally either impossible or criminal?
Google chairman Eric Schmidt's "private" visit to North Korea raises many questions, not least because he embodies what regimes in Pyongyang have spent decades resisting with all the considerable power at their disposal.
For the vast majority of North Korea's 24 million people, the global information revolution may just as well never have happened, especially when it comes to communication with the outside world.
In a country where radios are hardwired to tune exclusively to state-run broadcasts, surfing the Internet is, for most people, an entirely alien concept.
So while many observers puzzle over Schmidt's motives, just as many are asking what lies behind Pyongyang's courtship of the Google chairman.
Schmidt is part of a "private humanitarian mission" led by former New Mexico governor Bill Richardson, which is ostensibly focused on the case of a detained US citizen awaiting trial for alleged crimes against the state.
But state media has made North Korea's spin on the visit very clear.
"Delegation of Google Corp. of US Arrives" was the headline used by the official Korean Central News Agency (KCNA) in announcing their arrival Monday.
While North Koreans live in probably the most isolated and censored society on the planet and one that comes bottom of any media freedom survey, the country is not a complete IT desert.
Cell phones were introduced in 2008 through a joint venture with the Egyptian telecom firm Orascom, a domestic Intranet was launched in 2002 and some state bodies have their own websites.
It's a natural progression for an impoverished country desperate for investment, but in North Korea the economic imperative is always weighed against the potential for social disruption.
Thus the estimated one million subscribers to the sole cell phone system provider, Koryolink, can call each other, but not outside the country.
The domestic Intranet is similarly cut off from the rest of the world, allowing its very limited number of users to exchange state-approved information and little more.
Access to the full-blown Internet is for the super-elite only, meaning a few hundred people or maybe 1,000 at most.
For 95 percent of the population, none of the above are available.
Nevertheless, analysts like North Korea security expert Scott Bruce believe the expansion of IT access to five percent of the population is an unprecedented and highly significant development.
"North Korea has made a fundamental shift from a state that limits access to information technology to ensure the security of the regime, to one that is willing to use it as a tool, at least among a certain privileged class, to support national development," Bruce wrote in a recent policy brief for the East-West Centre in Hawaii.
This, Bruce concluded, opened a new policy option for the United States to engage with the North Korean IT sector and encourage its development in "an operation with the potential to transform the state over the long term".
Washington though has been vocally unenthusiastic about the Richardson-Schmidt trip, saying it was ill-timed in the wake of Pyongyang's widely condemned rocket launch last month.
Stephen Haggard, a North Korea expert at the Peterson Institute for International Economics, admitted to being flummoxed by Schmidt's visit, especially given Google's difficult history with China's censors.
"Google was forced into complex compromises, and faced substantial criticism, for efforts to sustain its China presence in the face of government censorship," Haggard said.
"We don't fault them for giving Pyongyang a try. But the information giant has more than met its match.
"Can you imagine (North Korean leader) Kim Jong-Un's response to a Schmidt PowerPoint on the liberating power of Google?" he added.
For all the regime's efforts, the information barrier erected around North Korea has, in recent years, begun to lose some of its prophylactic power.
Smuggled Chinese mobile phones allow people near the border to connect with Chinese servers and make international calls, while re-wired TVs allow access to outside broadcasting.
Smuggled DVDs, MP3 players and USB flash drives bring in everything from news to South Korean TV dramas that can't be shared on the Internet, but are passed from person to person despite the inherent dangers.
"North Koreans today are learning more about the outside world than at any time since the founding of the country," according to a recent study by the consultancy group Intermedia.
"Although the regime can and will likely continue to crack down on the influx of outside information, it seems true retrenchment is not possible," the study said.