Crossword clues for the word: FLAGPOLESITTING The word FLAGPOLESITTING has appeared as an answer to at least 3 crossword clues on different crossword puzzles. Crossword clues for FLAGPOLESITTING Showing 1 to 3 of 3 results Clue(s) Fad begun in 1924 Fad of an earlier era Undercover operation in front of the United Nations?