It would seem to me that you would hear nothing from the probe. The probe and all the information is was sending got sucked into the singularity very shortly after crossing the event horizon. Even if the event horizon shrunk to a diameter smaller than the probe itself, that information was destroyed by the singularity.
Well, even in the classical case (no Hawking radiation, black holes can only grow) we should be able to hear a
little more - we could hear the probe come closer and closer to the horizon, although we would have to wait ever increasing periods of time to collect ever shorter pieces of transmissions. The question is how much more we would hear when the consequences of Hawking radiation are added in the picture.
The probe and all the information is was sending got sucked into the singularity very shortly after crossing the event horizon.
Possibly, but for an outside observer, the probe hasn't crossed the event horizon, and will never have crossed it, no matter how long we wait. For the classical case, this would be the end of the story - the portion of the probe's flight below the horizon would simply lie beyond infinitely distant future for us, the remote observers. We couldn't hear transmissions from inside as we couldn't wait longer than infinitely long. For us, nothing could get out because nothing could get
in, in the first place.
But Hawking radiation screws everything up. First and foremost, as all the mass that ever fell in, including the mass of our probe,
will eventually be radiated out in a long but finite amount of time (at least in our thought experiment where we got rid of CMBR), this means that whatever we perceived as the horizon, can't really have been an event horizon to begin with.
As I hinted in my earlier set of questions, I can think of a couple of plausible scenarios what we might observe if we waited long enough. One thing we seem to be able to rule out is that the probe would simply continue to hang frozen above the shrinking horizon, as in the classical case. Eventually, the mass of the black hole will be less than the mass of the probe, by which time it will be obvious that the probe can no longer be hanging there. Thus the question is what will have happened to it by then.
First seemingly consistent possibility is that almost all of the infalling matter is still hanging above the horizon at the time we throw in our probe, and if we look
really well as we wait, we will see first the core of the original star and then more and more surrounding matter disappear at or near the central singularity, which for us lies exactly at the location of the apparent horizon (so we can't
really see the singularity itself) and reappear as Hawking radiation, which somehow escapes through all the outer layers of infalling stuff (possibly via some quantum tunnelling?). Eventually, we will see (in super slow motion) our probe get crushed by tidal forces and fall into the singularity as well. This would imply that the probe, from its viewpoint, wouldn't encounter significant amount of Hawking radiation as it falls in. It would just see the horizon recede in front of it due to general-relativistic effects until it is destroyed by the ever-increasing gravity.
Another seemingly consistent possibility is that the probe will never fall into the singularity, but will be blasted to pieces by the Hawking radiation of all the matter that had fallen in earlier, which gets converted to energy and hurled back at the probe before it has a chance to fall in itself. This would have been made possible by the fact that the horizon is not a real event horizon (as evidenced by black hole evaporation) and so it's not really the case that all paths must inevitably lead into the singularity. This would imply that the probe, from its viewpoint as it falls, would see the black hole under it accelerate in time and its Hawking radiation increase, until the probe sees the black hole for the explosion that it really is and becomes part of the explosion, instead of reaching the singularity.
Since both can't be true, I think theory should be able to rule out at least one of these possibilities. But I can't really tell which. Perhaps some of the experts here know more. And maybe this isn't even theoretically resolved yet and nobody knows. I wonder.