I have a few photos from one photo “shoot” that are always listed as most recent in the iPhone Photos app even though they were taken months ago. Why do they not sort by date as with other photos?
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Get info on a couple of the photos and tell us what the dates are on these photos. Also if you click on the date in the get info window you can change the date/time. Which is fine if you only have a few, rather than a few hundred... – Steve Chambers Jul 04 '20 at 17:03
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@SteveChambers - how do you change the date from Get Info? – Tetsujin Jul 04 '20 at 17:28
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@SteveChambers - I tried and couldn't change the date. – Natsfan Jul 04 '20 at 17:54
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Maybe your photos have the wrong date and is assumed to be most recent. – Natsfan Jul 04 '20 at 17:56
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There's an app called "A Better Finder Attributes" which is part of a very well-respected utility suite - but a tad expansive for a one-off change. Otherwise, there's this - https://apple.stackexchange.com/questions/99536/changing-creation-date-of-a-file – Tetsujin Jul 04 '20 at 18:21
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Odd, I just clicked on the date in the get info window in photos.app (Mojave) and another dialog popped up offering to let me change the date... In Catalina, not so much. Very strange. – Steve Chambers Jul 04 '20 at 18:55
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I use an app extension called ViewExif to look at the metadata.
If you have a date problem, those photos could be dated September 2021 and will be the newest until that date passes. That seems to be the easiest explanation. If not, then you’ll need to review the database - fix options with Apple or reset your library that stores the ordering of photos.
I would start with checking that the dates aren’t just not what you expect. It’s often a lot easier to change dates - look at this on the Mac Photos app if you can sync via iCloud or perhaps enable iCloud and use the web page to check as well.

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