What is the ruling on repeating the expiation for breaking an oath for someone who swore to abandon something, then did it, and was compelled to repeat doing it, knowing that he said "Insha'Allah" (God willing) sometimes after the oath?

If you swear an oath and then break it, an expiation (kaffarah) becomes obligatory upon you. If you repeat the oath and break it again, another expiation becomes obligatory. This differs from the Hanbalis, who only require a single expiation if you have not yet expiated for the first oath. Whoever swears an oath and says "Insha'Allah" (God willing) with the intention of making an exception, no expiation is due from him. Thus, for oaths where you predominantly believe you made an exception, there is no breaking of the oath and no expiation. For all others, expiation is obligatory. If the reason for your oath was curiosity, then expiation is not obligatory if you open Facebook out of necessity. In matters of oaths, one refers to the intention or the reason for the oath and what prompted it.