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I'm not surprised at him/his having difficulties with the exam

Is it him or his? Why is it so? What is the grammar rule here? What would be some other examples where this rule is used?

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There is no rule: both are correct and both are used. The object form is more common in speech than the possessive determiner.

As Professor Lawler elsewhere notes:

It's one variant, and falutes slightly higher, but with pronouns there are many idioms. Gerund clauses have two complementizers: the normal Acc-ing complementizer (without him telling me), and the Poss-ing complementizer (without his telling me). Both are correct, both are common, but Acc-ing is somewhat more common in practice.

Notice how he calls the accusative one the normal one: that’s the one with him.

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