One definition of key polynomials is as the weight generating functions of key tableaux. Assaf and Schilling introduced a crystal structure on key tableaux and related it to Morse–Schilling crystals on reduced factorizations for permutations via weak Edelman–Greene insertion. In this talk, we consider generalizations of both crystals depending on a flag. We extend weak EG insertion to a bijection between our flagged objects and show that the recording tableau gives a crystal isomorphism. As an application, we show that flagged key tableaux have a natural Demazure crystal structure, whose characters recover Reiner and Shimozono’s flagged key polynomials.