The note for "success" indicates the irony here. Of course, Satan is initiating another war with heaven, one that will be ultimately "in vain." No war with God could succeed. But it seems Satan has been "untaught." He has learned the lesson, and then the lesson has been "unlearned." I am not sure what has untaught him. I suppose, as the text indicates, it is his "proud imaginations" which untaught him.
There seems something psychologically true in that statement. We know today that one definition of insanity is trying the same thing over and over again and expecting different results. Yet, how many of us fall for that trap? We try to succeed in business with the same basic value-structures and methods that we tried the last time, when we failed.
There are many cliches in business about failing your way to success, but this has been shown to be a bias. We only hear the stories of those who have succeeded. Many people fail their way to more failure. Perhaps, that is what is occurring here with Satan. "His proud imaginations" gives him visions of success which will be in vain. Yet he will continue.
There is a kind of admirable quality in that. Pursuing despite the inevitability of failure. If you believe you are correct, this should be the only way to proceed. It is the courage to act on ones convictions.
I think of the play Cyrano de Bergerac, where the lead character will fail in all important realms of his life: productive, love and creativity. Nonetheless, to the very end he will not surrender his convictions.