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I have a standard owl familiar. While outdoors and flying, how far can it see?

How does this change from daylight to dusk?

How much of this can it recall?

I've seen the DM's guide on Visibility Outdoors and it says

When traveling outdoors, characters can see about 2 miles in any direction on a clear day, or until the point where trees, hills, or other obstructions block their view. Rain normally cuts maximum visibility down to 1 mile, and fog can cut it down to between 100 and 300 feet.

On a clear day, the characters can see 40 miles if they are atop a mountain or a tall hill, or are otherwise able to look down on the area around them from a height.

Does this mean that my owl can fly up a few hundred feet and see for 40 miles? Sure, I can't communicate with it, but it can fly back down to the 100 ft telepathic range and then relay what it saw, can't it?

Reasonably, how large an area could I tell it to go scout while I chill and cast a few rituals?

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This is going to be very DM dependent. The act of scouting will depend on what you expect to find. Is flying up a couple of miles going to detect the bandits sneaking up on your camp? No, probably not. Will it detect the village several miles away, in the valley? Yep. Conversely, a lower altitude, and therefore much smaller sight radius, will probably pick up nearby hostiles but lack information about the surrounding area. But, as a guide to what an animal remembers, the PHB says this in regards to Speak With Animals:

...The knowledge and awareness of many beasts is limited by their intelligence, but at minimum, beasts can give you information about nearby locations and monsters, including whatever they can perceive or have perceived within the past day... (PHB p.277)

So that at least gives a decent starting point in terms of what an animal/familiar could possibly recall after scouting around.

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