Imagine a simple, non-rotating black hole and a massive rocket that is free-falling past the event horizon of the black hole, linearly towards the singularity. The rocket is massive enough that it carries an appreciable momentum, and the linear velocity of the black hole will be measurably changed by addition of the rocket's momentum to that of the black hole.
An observer outside of the black hole is carefully, continuously monitoring the position and velocity of the black hole event horizon, and is able to detect the change in its motion dynamics caused by the free-falling rocket combining with the black hole.
However the rocket also has very powerful engines, and the captain of the rocket is able to make a decision after passing the event horizon as to whether to engage these engines to accelerate (briefly) at full power towards the singularity. The captain is instructed to only engage the engines in the case that some specific condition inside the event horizon is observed, and the external observer is also aware of this plan.
So my question is, will the dynamics of two cases differ in any way, from the perspective of the external observer? In the first case (no engine), there is a single collision between the rocket and the singularity at a predictable point in time. In the second case the initial collision will take place at a different (earlier) time from both the rocket and the external observer's perspectives, and with higher initial momentum - noting this is a more complex dynamic scenario as the rocket exhaust gases will also interact with the singularity via both gravitational attraction and eventually their own secondary collisions.
If the position of the black hole event horizon in the two scenarios varies at all for any instance, then the observer can accurately detect the signal that the captain of the ship issued and information can be transmitted out of the black hole via momentum signals. Even if the final momentum of the system may be the same in both scenarios, the intermediate dynamics may vary and this can be detectable.
The scenario could be simplified from a rocket to two masses held together with an explosive charge between them, without loss of generality. In this case the decision is whether the explosive charge is detonated or not.
It seems to me that the main transfer of momentum from the falling object to the black hole must happen when it collides with the singularity. So if the timing of the singularity collision(s) can be changed, then the timing of the momentum change(s) of the black hole will also vary and this should be visible to an external observer.
What do I miss in this scenario, that prevents information being transmitted externally?