Observations and theory suggest that core-collapse supernovae can span a range of explosion energies, and when sub-energetic the shockwave initiating the explosion can decelerate to speeds comparable to the escape speed of the progenitor. In these cases, gravity will complicate the explosion hydrodynamics and conceivably cause the shock to stall at large radii within the progenitor star. To understand these unique properties of weak explosions, we develop a perturbative approach for modeling the propagation of an initially strong shock into a time-steady, infalling medium in the gravitational field of a compact object. This method writes the shock position and the post-shock velocity, density, and pressure as series solutions in the (time-dependent) ratio of the freefall speed to the shock speed, and predicts that the shock stalls within the progenitor if the explosion energy is below a critical value. We show that our model agrees very well with hydrodynamic simulations, and accurately predicts (for example) the time-dependent shock position and velocity and the radius at which the shock stalls. Our results have implications for black hole formation and the newly detected class of fast X-ray transients (FXTs). In particular, we propose that a “phantom shock breakout”—where the outer edge of the star falls through a stalled shock—can yield a burst of X-rays without a subsequent optical/UV signature, similar to FXTs. This model predicts the rise time of the X-ray burst, t d, and the mean photon energy, kT, are anticorrelated, approximately as T∝td−5/8 .