Since the end of the 1970s, we have seen enormous progress in our understanding of the polar ionosphere and its structuring. With this benchmark issue of Radio Science it is appropriate to reflect briefly on that passage and some key questions that lie ahead. The discussion here will concentrate on the winter hemisphere, in keeping with the conditions under which most of the data studied to date have been gathered. The polar ionosphere alternates between two states, depending on whether the interplanetary magnetic field (IMF) is southward or northward. The former site is characterized by ~100--1000 km islands of enhanced F region plasma, originating in sunlit upper midlatitudes, entering and traversing the polar cap. They become highly structured and produce severe scintillation. Despite much progress on the source, evolution, and ultimate fate of this polar plasma, we remain challenged by the process(es) which chop entering plasma into such islands. For northward IMF we have learned much about the near-Earth processes determining the character of polar cap arcs, velocity structure and electrodynamics, and energetics. A remaining challenge is to relate these structures to the topology and driving physical processes in the magnetosphere and solar wind. Here we sketch the principles behind the progress and the context of several key problem areas ahead.