Pope speaking about fate of someone after death?

If the Pope says that someone is in Heaven/Hell, does that mean that person is in Heaven/Hell 100%?
Does it depend on if he is speaking Ex-Cathedra? and if it does, I guess, there is no point in him making such declarations non-ex-cathedra.

BTW, Has any Pope ever made such statements about a person's fate? (Outside of someone being canonized as saint?)

Thanks