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Linguistically speaking, the prefix "de-" connotes "doing the opposite
"un-" connotes "not."
If this were a hard-and-fast rule, undress, undo, unmask, uncurl, and a
number of other verbs would have quite different meanings. I think the
differences may be more in derivation (un- from Germanic, de- from
Italic) than in connotation. Undoubtedly, "de-" means "to do the
opposite of," but I don't think that would be a good justification for
choosing it over "un-." There may be better justifications.
I find "uninstall" easier to say, so I tend to stick with it. Something
about the consecutive high-vowel sounds just doesn't work well for me
(must be this regional dialect rubbing off on me). I would definitely
not hyphenate "uninstall" since "un" can't stand on its own.
billdb -at- ile -dot- com