Adam, Bug # 2644850 describes a problem with FileView's caching of icons. The problem is that BibDesk does not know that the URL has changed (and has no way of knowing) when a file is renamed on disk. So the FileView is never told to reload, and the _iconIndexMap cache is stale. So how essential is this caching? Would it be possible to simply forgo _iconIndexMap, and use only _iconCache? Or is there another way to do this?
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