Insight into how pairs JPEG+RAW files? I have full mismatches after import

Hi All, Over the holidays I was working to take my old DSLR photo archive (~30k images, stored as files/folders) and pull it into Photos on the Mac. From using different cameras over the years there were some Nikon RAW files, as well as JPEGs, who’s filenames (DSC_XXXX) would be the same while they were taken at different days/times. They were not shot as RAW+JPEG in camera.

When importing into the app would stack some of these as a RAW+JPEG despite the timestamp mismatch. In an attempt to correct, I “Export and Unmodified Original” the RAW+JPEGs which yields two files per ‘stack’, then used Transnomino to add the capture date/time to the end of the file name and reimported.

This appeared to work initially, but after some time had passed with photolibraryd chugging away the stacks of mismatched RAW+JPEGs would show up again.

Does anyone have any insight as to how Photos determines how to pair RAW+JPEGs and what steps I might take to resolve the mismatched stacks?

A couple few example screenshots are below.

Initial problem identification (right click on photo and select “Use RAW as Original”):
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Attempt to fix with date in file name, same issue:

View of files above in Finder after “Export Unmodified Originals”:

AFAIK Photos doesn’t care what the name of the file is (e.g. it won’t sort your files according to a date in the filename). In fact, when the files are imported they are given a filename with a UUID as the filename and the original filename is retained as metedata. If you want to get two files, like a jpg and a raw file, stored together in the library you have to adjust the date and time of one or both files after they are imported. It works but it’s tedious.

Hope this helps, and welcome!

Thanks for the welcome (long time listener, first time forumer).

It would make sense to me that file names were generally ignored and something like dates/times were used to differentiate or match photos to pair as RAW+JPEGs. But what I’m seeing is that Photos is associating photos taken at completely different dates/times as a RAW+JPEG pair. That behavior is what I’m trying to understand and work around.

Here’s some Finder snips of the Exported example above, with totally different creation times.

Here’s how they were named prior to import into Photos. This is leading me to believe that Photos is renaming them after thinking they are a RAW+JPEG pair, hence the recent ‘Modified’ date above:

Not precisely your situation but does this help at all?

I’m sorry to say this, but I think you went the wrong way. And if you still have your “old DSLR photo archive,” it is not too late to go back. If you keep photos in folders and files in your Mac or PC’s file system, you can use any one of many great photo editors. Affinity Photo and and PixelMator Photo, for example, are strong apps and not expensive compared to what’s out there. And since October of this year, Lightroom 7.0 no longer uses the “dreaded catalog” and permits local editing which makes their cloud optional. Apple Photos is not a strong app for DSLR raw photos, but maybe you shot everything on your DSLR as JPEGs?

I export all my iPhone photos out of Apple Photos as well as all of myDSLR and mirrorless photos to a simple folder and file structure. And I use Adobe Bridge and Adobe Camera Raw to edit them. I expect I’ll move to the new Lightroom one of these days.


That article certainly describes the functionality that I’m expecting, but doesn’t quite get at why the RAW and JPEG images taken at different dates / times are getting paired up together. Thats what I’ve been scratching my head over.

To some of @karlnyhus point, I’m wondering if asking to deal with the RAW files was my misstep. I do still have my old archive as I left it. I was lured to by the appeal of all of the photos synced via iCloud, on my phone, ease of bouncing between Mac, iPhone, etc. If I want to stay this course, I may be better off processing all of the RAWs outside of Photos and just importing JPEGs into Photos.

I’m not a huge editor, so while I have respect for the Lightroom / PixelMator crowd, if I’m honest with myself its not where I spend my time. For me the convenience of my whole library easily accessible on my phone and quasi-backed up via iCloud won out (at least until I hit this snag).

I think you may be on the right track of “just importing JPEGs into Photos.” Your iPhone shots naturally end up in Apple Photos. After processing raw photos from a DSLR, one typically exports the keepers as JPEGs for sharing with others. I keep my JPEGs in a subfolder with the original raw files, but importing them into Apple Photos, if you are willing to do that step, would give you valuable benefits.

Thank you for the help talking this one through. I think the general approach of just pulling JPEGs into is the right path forward to deal with my “archive” of photos to generally make them more available, surface memories and the like with widgets, etc. I was about to check the “Solution” box (foreshadowing), but then had quite the interesting experience with Photos.

Steps performed:

  1. Export “Unmodified Originals” for all RAWs from Photos, which includes all RAW+JPEG pairs.
  2. Delete all RAWs from Photos to wipe the slate clean, including “Delete All” option from “Recently Deleted” album (thinking this removes from iCloud given warnings about unrecoverable, etc.).
  3. De-dupe the exported folder of all RAWs (including JPEGs exported from RAW+JPEG pairs).
  4. Convert NEFs (Nikon RAWs) to JPEG with Nikon NX Studio
  5. Imported converted JPEGs and exported JPEGs back into Photos.

This all seemed to go pretty well and I let Photos chug away syncing back to iCloud for ~48hrs for the ~13,000 items.

Then after a few days of Photos processing through the imports I now see RAW+JPEG pairs showing back up, and RAW photos reappearing in my “Media Types” library! This is after deleting all RAWs and not re-importing any that weren’t converted to JPEG first.

I’m not sure what Photos is doing to bring these RAWs back from the dead. Do I need to repeat all my steps and wait 40 days or something for iCloud servers to really really delete the RAW images? This one is stumping me.

Sorry, I have very little insight into how Apple Photos works its “magic.” :slightly_smiling_face:

I’ve recently run across some photographers who say they rarely or never save JPEGs made from their raw files. Once they have posted such JPEGs, given them to clients, or otherwise shared them, they claim to delete them. Apparently figuring that they still have the original raw photos and associated edits and can re-export the JPEGs anytime they want.

I’m still thinking about whether I will let this practice influence my workflow at all. :man_shrugging:

Just a quick update that I have an Apple Support ticket open for the issue. The support person left me with some steps I’m working through similar to some actions I’ve taken above and I’ll report back if successful.

As a side note I came away pretty impressed with the Apple Support call. I very quickly was transferred to a Photos knowledgeable agent, did a quick screen share to show my problem and troubleshooting steps so far, and have a plan to test going forward. Don’t know if this was unique, but being my first support call in ages with them I came away impressed.

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