I think its possible for it to happen. I mean what if Dwebble's shell was destroyed and it was put in a Poke ball without being able to make another first.. With Oshawott's shell, if it was impossible for it to be returned to a Poke ball without it, why did they go through all that trouble to find it when it was lost instead of Ash just returning Oshawott to its ball and having it appear there with it.. I think if they get separated from their object and its really close to them, it gets put in the ball with them, but if its destroyed or blasted away to a farther distance, it won't be and it has to be found.
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They'll get a new object if they lose their own or look for it or something, but I'd guess they can.
A Kadabra could probably casually teleport a random spoon to its hand any second if it loses it, or use another item that works if no spoons are available. But pokémon whose belongings are more important like Farfetch'd, probably they'll desesperately try to find the thing and won't accept a random substitute.
Well, in a way, the video games had shown that items could be kept with a Pokemon as held items. It had to be, because once you gave a Pokemon an item, your bag space increased if you used them all up. The only thing is that they can't use the item with them inside.
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I'm more concerned about whether a Poke Ball can hold two Pokemon or not. I mean, it's been shown that it can't but yet it some how can hold a Pokemon that is more then one Pokemon.
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Dwebble's rock shell is hand-crafted, not really part of it. It's like a held item in that sense, especially since it can be broken (Shell Smash)
My headcanon is that there's a certain distance of separation allowed. If Kadabra faints and drops its spoon, the spoon gets recalled with it. Dropped down a large cliff, however, it wouldn't return on its own.
(Actually, that's probably not the best example. Twistedspoon is also a held item, but any spoon ever made probably works all the same.)
I think, however it works in the anime, Oshawott just didn't want to lose its precious shell, so they went to find it instead.