This is a classic problem in American option. Some discussion can be found in Shreve's book Ch 8 (8.4.1)
The problem can be summarized as find an exercise boundary, i.e. For example for a put option, we need to find a exercise boundary L(T-t), whenever the stock price S(t) falls bellow L(T-t), we should exercise. For your problem, it is the probability that lognormal distribution goes below L(T-t).
This problem is a little hard because it needs simultaneously solve PDE with several boundary conditions. So the common practice is to use finite difference (I know you don't like :-( ) to numerically find the boundary. Than you can calculate the probability.
More details, see Shreve's book. I think this is a popular issue. There should be many research papers talking about how to get the exercise boundary more efficiently (perhaps some analytical solutions :-) ).
best,



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