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My wife and I are also having this issue on iPhone 14 Pros and iOS 16.0.2. While we see each other has known AirDrop contacts sending a file results in a never ending waiting status and no notifications on receiving device. Yet the same device shows under “other” devices and we can send easily to that one.
Same problem here 🙄
 
Go to iCloud under setting. turn off contact. remove from device. then turn it back on. Sorted.
I finally fixed it by doing that after like an hour playing around with it. it must be glitch in the iCloud contact syncing if you happen to transfer from old iPhone to new iPhone using the transfer from old iPhone option and not via iCloud backup.
Can confirm this worked for my phone and my husbands phone. We set up the iPhones from a backup we did via iTunes. When I tried to air drop him he would show up twice under contacts and other (iPhone name). When he tried to airdrop me I would only show up as other (iPhone name). Turned off iCloud contacts and did not keep contacts on phone for both phones. Then toggled it back on and now airdrop works as it should. Thanks!!

Also to note I had two phone lists..one from iCloud and one on my iPhone. Once I did the toggle it fixed it so I just have the one iCloud contact list.
 
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***Airdrop Solution***

The new IPhone has messed up your contacts creating many duplicates or even bringing back some old contacts. “Link” the contact together. Once they are linked the airdrop will work again. This worked for me. Good Luck!
 
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