Shipping rules for group of countries (ex. UK or ITALY)
The OR and AND-groups takes all conditions inside of them with the chosen operator.

Your:

Condition 1: IT
--OR
----Condition 2: FR

Will be converted into ([Condition 1] AND ([Condition 2])).

Try putting both Condition 1 and Condition 2 in the OR-group:

--OR
----Condition 1: IT
----Condition 2: FR

This should be converted into ([Condition 1] OR [Condition 2]).
If that's what you're after.

Edit: Just a couple of minutes too late :)