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My parents use windows and iPhone, and I have to run tech support for them.

The windows photo import tool fails, because the photo's arn't really on the device, and apple lies to windows saying that they are available for import, so it fails halfway.

If I install iCloud for windows, will it sync photos to the laptop via photostream? or will it continue to delete photos after 1000 photos?

If photostream isn't enabled, will it start randomly deleting photos older then 1000 days that my parents take, without them understanding what is happening? or will it give some sort of warning / clean up prompt?

Or is this likely something they are already familiar with as (mildly tech illiterate) users.

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I have the exact same problem. Using on iOS over USB isn't recognized by Windows Photos, and doesn't show up in Explorer, even though the device is detected in iTunes.

I use iMazing. It's a third-party software, but it can open iOS devices when connected with USB. iMazing also can open a backup of an iOS device that is made with iTunes.

iMazing can export photos as .heic, save bursts as multiple photos, and save videos of Live Photos along with the .heic.

I've compared the quality and metadata of the downloaded files with the originals on the iPhone, downloads from iCloud web, and other general file transfer apps. I believe the iMazing versions to be the easiest and best.

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My issue ended up being driver related, what tipped me off was that the iPhone wasn't browseable in 'This PC' with DCIM available, so the photo app must have been using some alternate method of transferring the files.

Downloading the official drivers to make the iPhone show up as a removeable storage media device, allowed Windows Photo's to transfer all of the files successfully.

The files didn't seem to be packaged with iTunes as explained in https://support.apple.com/en-au/HT204095

So I ended up installing iTunes normally, checking for the drivers and not finding them, installing iTunes from the windows store, then following the instructions to update the driver in device manager.

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