Considering Elrond, Cirdan and Gil-Galad refused Annatar entry into the Grey Havens (despite disguising himself as an emissary of the Valar) and that Galadriel also didn’t trust the “Lord of Gifts”, why wasn’t that very same mistrust from the high Elves applied to the Istari once they arrived in middle-earth, as well?
Fascinating question! Some possibilities:
it was, actually, but the Istari proved themselves over time and by the end of the third age, the initial trust issues were no longer relevant enough for Bilbo and Frodo to put them in their book (likely, since after the whole Annatar thing the elves would have been even less likely to trust Maiar who were like "hi, I was sent by the Valar and I'm here to help")
Elrond and Galadriel have a sense for when Maiar are who they say they are (Galadriel because of exposure to Melian, Elrond because part-Maia nonsense) and their instincts aren't screaming at them with the Istari the way they were with Annatar
Glorfindel showed up at the same time as the Istari and vouched for them (idk how plausible that is, my grasp on canon timelines is a bit shaky tbh)
that's the explanations I can come up with off the top off my head. Probably other people have other headcanons. Thanks for asking!













