"Microsoft.. has adopted some clueful strategies.." Here's a word I should have known about, having to come up with crossword clues every day. Clueful means 'having the mental facility to figure something out'. As opposed to clueless, clueful is still a few clues short of making it into the dictionary.
WAIF, a homeless child, is a word which started life as 'weip' meaning 'tremble'. It later transformed into the meaning of something loose and floating about in the wind