Are you sure things are executed sequentially in that order? I would expect hypothesis strategies composed together to be lazily evaluated.
In any case, even in the case you describe, I would not expect the strategy to fail with probability 1. Remember that this generates multiple samples, and only one of these need to be valid.
In any case, even in the case you describe, I would not expect the strategy to fail with probability 1. Remember that this generates multiple samples, and only one of these need to be valid.