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3 results for CAULKED from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Fri Mar 26, 2021	38D	Filled in some gaps	Daniel Larsen	Shortz
Sun Nov 3, 1996	53D	Made watertight	M. Nosowsky	Shortz
Wed Jan 24, 1996	40D	Applied oakum to	J. Hess	Shortz

1 result for CAULKED from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Mon Sep 12, 1955	1A	Patched cracks with oakum.	H. L. Risteen	Farrar

Anagram:

22 ms