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Pa Toad said it was difficult to be Toad Sage for Naruto because of Kurama's chakra before he fought Pein.
Then in the recent chapter Kurama confirmed he didn't want to back then. He didn't wanna seem like he needed help.
But he was fighting 5 bijus and later Madara(who scares Kurama). Why wouldn't he have recommended doing so at that point, or when the juubi was revived?