Let A, B ⊂ M be inclusions of σ-finite von Neumann algebras such that A and B are images of faithful normal conditional expectations. In this article, we investigate Popa's intertwining condition A M B using their modular actions. In the main theorem, we prove that if A M B holds, then an intertwining element for A M B also intertwines some modular flows of A and B. As a result, we deduce a new characterization of A M B in terms of their continuous cores. Using this new characterization, we prove the first W * -superrigidity type result for group actions on amenable factors. As another application, we characterize stable strong solidity for free product factors in terms of their free product components.