Despite ups and downs in the relationship, Madeleine Albright - then secretary of state - visited Pyongyang in 2000 and an arms control treaty was agreed.
Mr Obama's trip predictably failed to produce breakthroughs on either issue, though a lengthy joint statement outlined measures to step up co-operation on developing clean energy.
If the confrontation has crystallized in this latest battle, it may already be heading toward a predictable conclusion: In the long run, the tech companies are destined to emerge victoriously.
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