I've seen a few posts on the internet which seem to suggest that an observer never seeing a particle crossing the horizon is an idealization for a massless particle. If the particle is massive some mechanism will cause the horizon of the black hole to rise up encompassing the smaller mass within a finite amount of time from a distant observer's perspective. "Kevin Brown" also seems to argue this point in his book (if I interpreted it correctly)
How valid is this interpretation compared to the seemingly more standard one where particles, massless or otherwise, become "frozen" at the event horizon? In the standard interpretation as the horizon expands, the "frozen" material will be "pushed" outwards with the expanding horizon and will never actually be encompassed by it. Meanwhile, Kevin Brown notes that "there is no known mechanism for that to happen."