From an outside observer, presumably you shoot a laser at a black hole and if your photons don't hit anything on the way to the horizon, they never hit it either but just approach asymptotically as time goes to infinity.
As, a photon though, you don't "notice" crossing the horizon and in a measurable amount of time you go from being emitted to hitting the singularity.
Black holes don't last until infinity though, they evaporate in a large but measurable time. (let's say 10^100 years, it depends on time and how the universe dies and how big the black hole is, but whatever, presuming it happens it is some extraordinarily large number of years)
So... as something falling into a black hole an outside observer will watch you infinitely slowly approaching a growing horizon until at some point the growth goes negative and you watch the horizon falling away from your friend the photon until at last the horizon disappears entirely and releases the photon to go about its merry way to hit something sometime around the heat death of the universe.
In other words, if you are a conscious very resilient little particle doomed to fall into a black hole... do you really appear from the outside to be falling in until the black hole evaporates? Do you experience going through the event horizon like it's nothing and hit the singularity in a few hours by your own watch...
Or is a black hole sort of a time machine to the end of the universe where in the short process of falling in you get to watch the whole history of existence pass you by and you come out at the end having never crossed the horizon in what was for you a very short ride.
Or is there some third option where from the outside it takes an infinite amount of time for you to fall in, but that infinity "for math reasons" actually takes place and passes in a Zeno's paradox kind of way at some distinct point in your timeline and you meanwhile pass the horizon and hit the singularity in short order and are no more?
I don't really know anything but these are questions and vague thoughts I have had. The central question is reconciling the outside apparent infinite time to watch something cross an event horizon with the finite lifespan of evaporating black holes.