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Syncing iPhone photos back to iMac is problematic
#50600 12/06/18 08:13 AM
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Ever since upgrading my Mid-2011 iMac to macOS Sierra 10.12.6 (from Yosemite, I skipped El Capitan), any photos or video taken on my iPhone are very slow to sync back to the Photos app through iCloud, on the order of 2-3 days. Lately it's not happening at all. If I take a photo on the iPhone, if I open the Photos app on the iPhone, all photos and videos sync to iCloud immediately if I'm on WiFi. In Yosemite, that used to also get them to show up in Photos on the Mac quickly as well.

I've taken a few videos and about 25 photos since mid-October and none of them show up in the Photos app on my Mac. It always says "Updating..." at the bottom of the Photos window, but none of the latest ones show up.

I can go into iCloud and see them there, and I download them from there if I need to, but it's a lot more hassle. I've rebooted several times since October, and logging into and out of my iCloud account on the iMac doesn't seem to help either.

Anyone have any ideas how to fix this?

Last edited by Rick Deckard; 12/06/18 08:19 AM. Reason: clarity
Re: Syncing iPhone photos back to iMac is problematic
Rick Deckard #50605 12/06/18 01:19 PM
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  1. Where in Photos are you looking for the images?
  2. What are your specific settings in System Preferences > iCloud > Photos > Options?
  3. What is your setting in Photos > Preferences > General > importing?
  4. What is your setting in Photos > Preferences > iCloud?
  5. Have you run Disk Utility > First Aid (or Drive Genius, TechTool Pro, or whatever) to see ir there is file or volume structure damage on your drive?
  6. How much free disk space is available on your iMac?


If we knew what it was we were doing, it wouldn't be called research, would it?

— Albert Einstein
Re: Syncing iPhone photos back to iMac is problematic
joemikeb #50606 12/06/18 03:26 PM
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Thanks for the reply. Here are the answers:

1. When I open Photos on my Mac, "Photos" is selected in the sidebar so all photos are shown, listed in date order, the newest at the bottom of the main window. There it shows the number of photos and videos synced to the Mac, and below that it says "Updating..." but never really updates.

2. iCloud Photo Library and iCloud Photo Sharing are checked, iCloud Photo Stream is unchecked.

3. Importing has "Copy items to the Photos Library" checked.

4. iCloud Photo Library is checked with "Download Originals to this Mac" selected. My Photo Stream is unchecked and iCloud Photo Sharing is checked. (These settings are identical to what is set in the iCloud system preferences Options section)

5. Disk Utility reports no issues. I have DiskWarrior and can run that as well if you think I need to.

6. I currently have 156GB+ free on my 2TB hard drive. Not as much as I'd like, but I can offload and delete some files if that's the issue.

I'm guessing the problem is with not having the My Photo Stream option checked? Funny thing is, this has been working just fine until recently and I haven't changed that setting, it's been unchecked for well over a year.

Re: Syncing iPhone photos back to iMac is problematic
Rick Deckard #50607 12/06/18 06:12 PM
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I don't see anything obvious that would effect download from iCloud to your iMac. It sounds suspiciously as if there is a "damaged" file somewhere in the system. There are a few things you might try, but not necessarily in this sequence. My advice would be to read and understand all of the options before choosing your first course of action...
  1. Logic would seem to indicate the first image that failed to download has the highest probablility of being damaged so…
    1. Log onto iCloud > Photos and export the first image that did not download to your computer or your iCloud Drive
    2. Delete that image from iCloud Photos
    3. Cross your finger and hope the other images do download. 🤞
  2. Worth a try…
    1. In Photos > Preferences > iCloud > iCloud Photos change "Download originals to this Mac" to "Optimize Mac Storage"
    2. This will replace the images on your iMac with smaller imaged optimized for display on your iMac screen
    3. the full resolution images will be retained on iCloud but the difference will be invisible to you. If you Edit an image on your iMac it will be the full resolution image on iCloud that is changed as well as the optimized version on your iMac and your iPhone.
    4. The whole process will be invisible to you.
    5. This might allow the optimized image to be downloaded to your iMac instead of a damaged full size image
  3. Assuming you have a Time Machine backup:
    1. In Finder Select the folder /Users/yourid/Pictures
    2. CLick on the Time Machine icon on the menu bar
    3. Form the drop down menu select "Enter Time Machine"
    4. Using the Time line on the right side of the Time Machine window scroll back in time to a date when you know the Photos were downloading from iCloud correctly (NOTE: this may take several seconds but watch the date to the right of the Finder window)
    5. Select the Photos Library icon
    6. Click on Restore
    7. This will restore the Photos Library to a point in time that you know it was working. If the problem was a damaged database the new images should be downloaded from iCloud but it may take a few days.
  4. Or…
    1. Follow these instructions from OS X Daily to create a new Photos Library.

Last edited by joemikeb; 12/06/18 06:19 PM. Reason: #^A$% spell checker

If we knew what it was we were doing, it wouldn't be called research, would it?

— Albert Einstein
Re: Syncing iPhone photos back to iMac is problematic
joemikeb #50653 12/11/18 02:23 PM
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Thank you for the detailed reply.

I tried deleting the 5 photos taken immediately after the last imported ones, but to no avail. Same problem.

I have not tried optimizing storage yet and I don't have a Time Machine backup (I use clones instead).

I also have not tried creating an new Photos Library, though I did try repairing it. The repair completed OK, but afterward my Photos window now constantly says "Uploading 74 items" but they never seem to upload.

I'm guessing there is some corruption in my Photos Library of some kind and I'll try creating a new library eventually to see if that fixes it. Since I currently have a workaround by logging directly into iCloud to download photos and videos, I'll let it go for now.

Re: Syncing iPhone photos back to iMac is problematic
Rick Deckard #50654 12/11/18 04:36 PM
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Originally Posted By: RIck Deckard
I have not tried optimizing storage yet and I don't have a Time Machine backup (I use clones instead).

I will spare you my diatribe on why cloning is an inadequate replacement for Time Machine, but I encourage you to switch to "optimized" images on both your iMac and iPhone. They take up a LOT less storage space, which is particularly useful on the iPhone and you can edit the image on either device and that edit will effect all your devices including the full resolution image on iCloud. To my way of thinking it is a real win-win solution.

Originally Posted By: RIck Deckard
I also have not tried creating an new Photos Library, though I did try repairing it. The repair completed OK, but afterward my Photos window now constantly says "Uploading 74 items" but they never seem to upload.

It sounds as if something is crumbling. Don't wait too long to create your new library, Turning it on takes only several seconds, but populating the new library can take a while and if you switch to "optimized" images that can take many hours, even days to completely settle. One thing more, you probably want to designate the new library as the System Library once it is created.


If we knew what it was we were doing, it wouldn't be called research, would it?

— Albert Einstein
Re: Syncing iPhone photos back to iMac is problematic
joemikeb #50681 12/15/18 10:31 AM
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Originally Posted By: joemikeb
I will spare you my diatribe on why cloning is an inadequate replacement for Time Machine, but I encourage you to switch to "optimized" images on both your iMac and iPhone. They take up a LOT less storage space, which is particularly useful on the iPhone and you can edit the image on either device and that edit will effect all your devices including the full resolution image on iCloud. To my way of thinking it is a real win-win solution.

I'm not opposed to using Time Machine, but I would never trust it as sole backup due to reading about too many bad experiences people have had with it. I usually recommend people have both a clone and a TM backup, but right now I don't have enough external drive space right now for a TM one. I will eventually.

Originally Posted By: joemikeb
It sounds as if something is crumbling. Don't wait too long to create your new library, Turning it on takes only several seconds, but populating the new library can take a while and if you switch to "optimized" images that can take many hours, even days to completely settle. One thing more, you probably want to designate the new library as the System Library once it is created.

I will try optimizing storage for photos then and the new library too. Would there be any issue with the optimization process causing issues with a clone backup if files are saved to my photo library while the backup is occurring? I believe SuperDuper does some kind of checking at the end of the backup process to compare against the original, as I had failures occur many years ago when I would leave Safari open and a webpage would change in the background. Guess I can just try it and find out, and turn off backups for a day or two while it's occurring if it causes problems.

Re: Syncing iPhone photos back to iMac is problematic
Rick Deckard #50682 12/15/18 01:56 PM
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The safety net is iCloud always has the full resolution image and is therefore available as a fail safe. But personally I would not run a clone diluting the transition phase. No specific reason other than I would not be comfortable with the resulting clone.

As to the reliability of Time Machine backups, the only issues I have was shortly after The Machine was first released and one other time when a factory rebuilt hard drive failed. I have had zero issues in the last four years.


If we knew what it was we were doing, it wouldn't be called research, would it?

— Albert Einstein
Re: Syncing iPhone photos back to iMac is problematic
joemikeb #50683 12/16/18 01:03 AM
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I think I have solved the issue. I deleted the last shown photo from within Photos on my Mac (the one at the bottom of the window). None of the files in iCloud would download after the date of that last photo, but after removing it, closing Photos, and opening it again a few minutes later, they all appeared.

Just to test, I took a new photo with my iPhone and closed Photos on the Mac. I waited a minute and the photo appeared within Photos just like it should.

Thanks again for all your help!


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