Anael is, to say the least, surprised to be summoned from her post, by Michael himself, no less—she wonders if she is to be chastised for exceeding her orders by studying humans rather than simply observing them, if she is to receive instruction on how to handle Uriel's recent change of attitude towards her—but no, she was chosen specifically because she has been studying humans, no one knows of this save herself and Michael; obeying this order will likely end with her death, she knows, but she is glad to obey.

Anael whispers her name into Amy Milton's ear, but the influence doesn't quite take; Anna Elizabeth Milton is born and lives and grows and forgets, until Pamela helps her remember, and then Anna babbles a mix of lies and truths while she sorts out her memories and tries to figure out how to resolve Michael's orders with the consequences so far of obeying them; Anael finally settles on defining 'establish yourself as a trusted ally of this man' as including 'seduce this man', in part because Dean's wiring is such that it'll work but mostly because sex and chocolate cake might be acquired tastes but Anna isn't lying when she tells Dean life without them sucks.

She has yet to reconcile Anna and Anael when Castiel sells her downriver, and whatever Michael's plan is, it doesn't include the rescue of one rebellious ex-commander, so when Anna spots a crack in her cage wall, she uses it, but Anael notes the hints of Michael's Grace and wonders; it's Anna's idea to scatter Sam Winchester's remains from here to the Andromeda Galaxy, but when Castiel short-circuits that plan, Anael remembers her standing orders and chooses to ensure Sam's destruction at a time when John Winchester is alive and trusting and vulnerable, rather than a time when John's reaction to the supernatural is shoot first ask questions later or a time when there's no John to worry about, though a shorter journey would be easier; Anna survives the jump better than Anael, but not so well that either remembers Anael's reasoning for her choice of battlefield until Anael sees Michael; Anael dies first, so when she realizes exactly what being a good little covert operative gained her, Anna doesn't even have the chance to tell herself 'I told you so'.