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In Bag End, Gandalf and Frodo are talking about extremely sensitive topics with the window wide open. Anyone could have listened in to their conversation and ran off to gossip about it all over Hobbiton. Indeed, somebody did eavesdrop! Sam. They were just lucky he happens to be so loyal and non-evil.

Then, not much long afterwards, Frodo appears to have learned nothing. In the Prancing Pony inn, they again (albeit without Gandalf present) sit and discuss extremely sensitive matters, repeatedly referring to Frodo with his real last name, with the window wide open in the parlour.

Strider should have known better, but only after they have already laid out all the information does he shut the window. One of the Black Riders could easily have been lurking outside, even if they don't attack physically in the daytime.

Both Gandalf and Strider (Aragorn) are shown to be extremely intelligent, wise, resourceful and careful in general, except for these two instances. Of course, "the story dictates that it has to happen" with Sam so that he has an excuse to go with Frodo, but in the second example I've just given, there seems to be no reason that they had to sit with the window open in there. In fact, I assumed that it was locked tight until the moment that the book describes to me that Strider finally shut it.

Would I ever bother to ask a question like this for a poorly written book? Hardly. It is only because of the attention to detail and ultra-high quality overall of this work that I do so. I feel as if there's probably an explanation which I haven't thought of.

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    Hobbits are innocent and wouldn't even think of eavesdropping and spying and such things... At least at the start of the tale. And Gandalf is both preoccupied and feeling safe in Shire and has "gone native", catching some of hobbit way of thinking along the way. It takes Gandalf a while to go back from "peace mode" to "war mode". But I don't have my books at the moment so I hope someone else answers it.
    – jo1storm
    Commented Apr 14, 2022 at 10:44
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    I think the idea is to portray that these are not professional spies and infiltrators. Frodo in particular acts very foolishly at the start of the book
    – Valorum
    Commented Apr 14, 2022 at 12:32
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    I haven't read the books for a long time so this is headcanon comment rather than an answer - I'd always assumed Gandalf had known all along that Samwise was outside listening but since Gandalf intended for him to accompany Frodo he let the pretence last until it suited him to 'discover' Sam, with the bonus that it gave Gandalf the leverage to encourage Sam to accompany Frodo to Rivendell. Tldr: Gandalf knew it was Sam outside, if it'd been anyone else he'd have shut the window.
    – Wiggo the Wookie
    Commented Apr 14, 2022 at 12:50
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    Two reasons. (1) They didn't have central heating. Seriously: in a world before furnaces, underground houses would be pretty chilly and windows needed to be open on a summer day. (2) In a rural area, unfriendly lurkers at the window are not exactly common, and unfriendly lurkers at the window would meant he game was already up.
    – Mark Olson
    Commented Apr 14, 2022 at 13:55

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They have great senses, including hearing, and usually would hear someone else around. Plus, as mentioned in comments, they are relatively innocent, not used to having people nearby that they don't know who could overhear something. At The Prancing Pony, Aragorn lets them know something of his abilities:

He got up and went to the door, opened it quickly and looked out. Then he shut it quietly and sat down again. ‘I have quick ears,’ he went on, lowering his voice, ‘and though I cannot disappear, I have hunted many wild and wary things and I can usually avoid being seen, if I wish.

Rural people often don't even lock their doors, since who is going to walk miles and enter without permission? The hobbits may not be used to paranoia, but Aragorn certainly is. Note that he lowered his voice, and we can assume his voice was pitched low enough to make it difficult for eavesdroppers to hear.

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