Recall Cadsuane's disdain for how "poorly" she "handled" Rand, how little she "prepared" him to meekly follow Tower guidance. Moiraine tried that tack and found out the hard way it only put his obstinate back up so she did what she should've from the first: She worked her butt off to earn, justify, his trust.

That may have been the first time since Callandor and the Stone that a male and female channeler worked together on anything. First as equals and then with Rand in charge. Mo learned the hard way she had to treat Rand with the respect he'd earned and couldn't hold out on him. She put her cards on the table to an extent that shocked Rand even knowing why, and it paid very nice dividends.

Caddy managed to undo that very nicely and very quickly. Even when she wasn't directly responsible for things that alienated Rand, made him suspicious and harder, when her insistence no one else was competent to lead caused problems because she's fallible (a major recurring theme in WoT) it usually had disastrous results for Rand. She was so sure she knew what both Rand and Elaida's embassy were doing that it took Sulin to figure out he'd been kidnapped, and thus days of torture before he was free. I really can't fault her on the DB, but I can see why Rand does. It's the same old thing: The price of insisting you're perfect is finding out you aren't, and when you're very very good it only makes your rare failures that much more unexpectedly epic.

Mo worked incredibly hard to give Rand a confidant and an ally, which he consciously and keenly misses. Caddy did a fine job of reminding him he can't trust even those most loyal to the Light. I expect this will... perturb... Moiraine.