Can I AirDrop multiple attachments and messages from iPad to iMac?

on my iPad I have more than a hundred attachments to Messages. I want to send them to my iMac. How do I Airdrop multiple attachments? Or must I Airdrop them one-by-one?


[Re-Titled by Moderator]

Original Title: airdrop multiple attachments from iPad

iPad, iPadOS 17

Posted on Aug 1, 2025 11:02 AM

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Question marked as Top-ranking reply

Posted on Aug 1, 2025 12:56 PM

You would need to save them from the Messages App into the Files App for instance and from there you can select. multiple files to AirDrop.


With that said, is your Mac not getting the messages from your iPad?

iMessages on your iPad should appear directly on the Mac if both devices are using the same Apple Account.


Or are you using a specific App on the iPad for these messages?


4 replies
Question marked as Top-ranking reply

Aug 1, 2025 12:56 PM in response to dougieboy

You would need to save them from the Messages App into the Files App for instance and from there you can select. multiple files to AirDrop.


With that said, is your Mac not getting the messages from your iPad?

iMessages on your iPad should appear directly on the Mac if both devices are using the same Apple Account.


Or are you using a specific App on the iPad for these messages?


Aug 1, 2025 4:14 PM in response to Phil0124

Phil0124 wrote:

You would need to save them from the Messages App into the Files App for instance and from there you can select. multiple files to AirDrop.

With that said, is your Mac not getting the messages from your iPad?
iMessages on your iPad should appear directly on the Mac if both devices are using the same Apple Account.

Or are you using a specific App on the iPad for these messages?

Could zip the files.

Aug 14, 2025 5:46 AM in response to LotusPilot

Thank you LotusPilot

There are a few dozen GB of attachments to Messages. I use only the free 5GB version of iCloud. I back up my data up on some hard drives, including one for Time Machine.

I am having to Airdrop a couple of hundred attachments to Messages from the iPad to my iMac so I can give the iPad away. It would be handy to do that all in one action or perhaps 50 attachments at a time, instead of one by one.


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Can I AirDrop multiple attachments and messages from iPad to iMac?

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