In truth... Uchiha Madara was overthinking it.
Emiya Shihara did not care at all about the Ten-Tails that might be resurrected in the future of the Shinobi World, and he had already told Uchiha Madara everything that happened after his own resurrection.
For instance... Uchiha Obito, in his scramble to seize control of the Eye of the Moon Plan, had ordered his subordinates to kill a Tailed Beast, causing their plan to capture the beasts to be delayed indefinitely rather than starting early.
Chapter 186