With USB cable connection (no cloud) to import from updated iPhones (11 Pro Max, 12 mini, and 13 with their updated iOSes) into macOS (Ventura v13.x, Big Sur v10.11.x, and Mojave v10.14.x)'s Photos app, I noticed imports show already imported medias and missing brand new medias. Is there another annoying bug with local USB connection without cloud? 
Thank you for reading and hopefully answering soon. :)
@Ant Dude - this doesn’t sound like quite the same problem, but it does involve iPhones, images and the Photos app, so here goes 
I have tried importing photos, via cable, from my 3 family members iPhones into MacOs photos on my Mac (they all have their own separate Apple IDs). Far less than half the photos show up in the photos app on my Mac (desktop). In fact on my daughter’s phone only about 10% of her > 5000 images showed up in the photos App!? After several attempts, I gave up on that . I have also given up on using Apple apps to transfer the photos.
Instead, I have used machines associated with each family members own Apple IDs (their individual MacBook Air(s)) and downloaded all their images (cloud and otherwise) via their machines to an external SSD. From there I’ve transferred the images to my own disk and imported them into my Lightroom library and catalogue.
For some reason, perhaps connected to the amount of memory on the different MacBook Airs (?), I wasn’t able to transfer more than about 1000 images at a time without the process crashing. Anyway, it wasn’t too difficult, and I now have an extra 15k or so images in my LR library (about 90% of which are junk). Nonetheless, sorting, cataloguing and deleting junk in Lightroom is infinitely easier than in the Photos App - and with the added benefit of having all my and my family members photos in one place…
In iPhone 11 Pro Max, it has almost 20K medias. 13 has like hundreds. 12 mini has maybe 50. I don’t think it is a memory issue. Also, why would older macOS versions also have this issue too? Did Apple change something in its iOS? Is Lightroom free? Apple’s QA is really bad these days. :(
In respect of the memory, I was talking about the MacBook Airs “freezing / crashing" when I was transferring the images from them to the SSD (nothing to do with the iPhone). FWIW, this is only a guess …
No, unfortunately Lightroom is not free. For a photographer, Adobe has a really good-value subscription package which gets you Lightroom and Photoshop. However, unless you are cataloguing and/or editing plenty of photos it is probably not worth it (and there’s a bit of a steep learning curve).
Thanks. I’m just a basic/simple guy. Don’t need a fancy setup. Just want it to work!
Does anyone have problems importing iPhon… - Apple Community shows another user with this problem in his Sonoma. It seems Apple did something in its iPhone’s iOS since Mojave v10.14.6 has the same problem. What’s up? Grrr.
I’m running Mojave (10.14.6) and use an iPhone SE3 (iOS 17.4.1) and can successfully import photos from the phone to the Mac via USB2–Lightning cable and Apple’s Image Capture. No Apple ID or iCloud is involved.
I do not use Photos so I import to a folder rather than the app. I then import into Lightroom.
Just another data point.
I’ve been meaning to post about this for a while now but…
Yes. I’m having similar problems. I think I started noticing it when sometime during io
OS16 but it still happens on 17.3.1
The Mac in question is a Mini running 10.12.6 the the photos library is on an external disk. iCloud is not used.
Every time the phone is plugged in the Mini shows all the photos on the phone - even those that have been imported over a year ago.
The ‘recently imported’ display across the top does show pix that are recent imports. It does also put up a ‘this image already exists’ window when trying to import an image that has already been imported.
However. the biggest issue I am having is that importing new images is very hit and miss.
e.g. I select 12 images to import. It will import 1 or 2 and then (after a considerable pause) puts up a window saying that either the other files are corrupt, or nul, or in an incorrect format.
It has got so bad recently that I now use iMazing to access the photos on the phone and import them that way.
None of the above applies when importing from SD cards!
OK, I am not alone. Good. We need to let Apple know about this via its Feedback (Product Feedback - Apple) and bug report (Bug Reporting - Apple Developer). Apple has too many bugs. :(
I have been using Image Capture for several years now - I forget how long.
I want to put pictures into dated import folders, rather than directly into Photos anyway.
I think there might have been issues with importing into Photos, but I forget that, too! 
MY import to the Photos app broke over the last weekend. I see all of the images to be imported and this looks right (about 500 now), but clicking Import All New Photos just throws me back to the Library list without importing anything. No OS or iOS changes that I know about over the last weekend either. MacOS 14.4.1, iOS 17.4.1.
Interestingly Lightroom Import still works fine (yes, I use both).
Since Apple broke this Photos app’s import, is there a free alternative macOS app that is easy to use?
“Since Apple broke this Photos app’s import, is there a free alternative macOS app that is easy to use?”
It’s not free, but Photosync is worth every penny. It can transfer photos to/from pretty much anywhere to anywhere. There’s a desktop companion app (free) that lets you set up what you want to do with them on the mac end, such as into Photos, into specific folders, by date or album and much more. I’ve been using it for years to dump iThing photos into device/dated folder hierarchies for import to Aperture. The premium version will backup new photos in the background, talk to real cameras over wifi or usb, and some other features. Cross platform including linux. Perpetual or subscription. Perpetual is $6 or $25.
Just for kicks. I deleted my macOS Ventura v13.6.7’s Photos app’s ~/Pictures/Library.photolibrary, relaunched Photos app, started a new library filename to be in clean/new state, imported all of my 99 images (small collection) from my iPhone 12 mini (iOS v17.4.1), again saw most of them and a few missing recent ones, exited Photos app, relaunched it, went to import my iPhone’s images, and again still see some of the already imported images. Yeah, Apple broke something its Photos import from iPhones. :( I left feedback and bug report to Apple about this issue. I hope they will look and fix it. We all need to do this.
Just so you know, you don’t need to delete your library. If you hold down Option when launching Photos, you will be presented with a dialog that will let you create new libraries and select the library to open (from a list of previously-opened libraries):
Once a library has been created, you can also double-click it to open Photos with that library. Launching the Photos app normally (from it’s app icon) will cause it to open whichever library it used on your previous session.
So if you want to perform a test with a new library, you can just create a new library and use it for your testing, leaving your pre-existing library unchanged.
It was suggested earlier in this thread to use Apple Image Capture and import from the iPhone to a folder on your Mac. This is one way to determine if the problem is the Photos import. Have you tried this?
Yeah, I did involving extra works. :(
Did it work?
Catching up here with a few thoughts:
As others have mentioned, I’d absolutely try Image Capture.
It seems like there’s a lot of mixing of old versions of macOS and new versions of iOS. That feels to me like a place where there could be a mismatch since Apple is less likely to test with obsolete versions of macOS.
iMazing might also be useful here.
Yes, Image Capture worked but it is more work to manage instead of directly in Photos app unless there’s a way to have it import directly into Photos app by itself. Randy said he had the same problem in his updated macOS Sonoma. I don’t want to upgrade macOS to make Contacts’ sync break (still works in my Ventura). Apple’s QA is really crappy. :(
I haven’t used USB syncing in many years, but I seem to remember that the idea was that you’d import from your iPhone into Photos, deleting the copies from the iPhone in the process, and then you’d sync the desired albums back to the iPhone. That way, you’d only be importing new photos on every pass, which would keep the number to process and import much lower. And it should avoid issues with knowing what has already been imported.
I can’t tell from what people have said so far if doing that (or not doing it) plays a role in what’s going on here. Certainly, if you leave every photo you ever take on the iPhone, there will have to be a lot of intensive comparison against what’s new and what has already been imported on every pass.