Why does it care Because it's a superintelligence that wants all sentient beings to flourish, presumably, this isn't actually confusing.
"Because I Gated you to Velgarth?" he says, wearily. "I - am pleased, about that."
His instinctive response here is to leave it at that, not give Sing any more information on his internal state, but - why? It can probably infer enough, and this shouldn't have to be adversarial, and...well, Sing is the one entity who isn't going to judge him, because it's alien, it doesn't do human moral judgement.
"I wish it had not needed to be so hasty; I am quite sure now that I gambled right, but - it is not the kind of decision one ever wants to gamble on. I wish it had happened two thousand years ago. Or - that I had known, at least, that I could somehow have guessed this outcome and planned toward it, and not..." He waves a hand vaguely. "Not so much waste."
He lets his breath sigh out. "And I am very tired. I am not sure why."