OS: OS X 10.10.3 (Yosemite) Machine: Macbook Pro (Retina, Mid 2012) iPhone: 5s on 8.2 (12D508)

So I import all photos/videos off of my iPhone to Photos on a daily basis after upgrading from iPhoto and it works well overall, so far.

The problem is that, while Photos does give me the option to "Delete items after import", the option becomes greyed out after some imports and there are some items that get left behind on the iPhone (they are successfully imported but do not get deleted).

iPhoto would let me delete already-imported photos, but Photos does not. I also do not sync Photos using iTunes.

I have two inconvenient workarounds to this:

  1. Select all photos in Photos app, check "Delete items after import" and click "Import Selected" again. This may or may not create duplicates -- I'm not sure.

  2. Manually delete each photo on my iPhone like a cave person

So my question is this-

Is there a more automatic way to do this (without duplicates), since I'm doing it on a regular basis?

  • Does your iPhone participate in any or all of "iCloud Photo Sharing" or "My Photo Stream" or "iCloud Photo Library (Beta)" - the status of each of these has subtle (and mostly undocumented by Apple) implications for how the "camera roll" behaves on iOS 8.2 and later in my experience. Similarly, does the Photos app on Mac participate in any of the above?
    – bmike
    Mar 25 '15 at 19:24
  • I also use your 2 methods. They both lead to errors. [return] I often feel like a "cave person" with Photos.
    – dan
    Nov 5 '18 at 12:46

I'd go for the 'not quite cave-man' approach - though still a bit manual...

  • Launch Image Capture.

  • Plug in iDevice

  • Select any/all photos you wish to delete

  • The Delete button is at the bottom of the window [the 'no-entry' sign]

After comments - the button is still there in Yosemite.

Update Nov 2015 - the button is still there in El Capitan, though it is now black & white, not red.

Picture updated to Image Capture 6.7 after further queries on the button not being there.

Update July 2016, as people are still missing this bit...

If the Delete button doesn't appear, eject & re-plug the phone.

enter image description here

  • 3
    This works but its so lame. Hope apple will release an update soon... But thank you for this tip!
    – neoswf
    May 17 '15 at 2:43
  • 1
    @Tetsujin I can't see this button in Yosemite. Are you sure they didn't remove it?
    – Shmidt
    Jun 16 '15 at 3:00
  • 1
    Using image capture with el capitan, I also do not see the delete button. Oct 12 '15 at 5:27
  • 1
    Delete button highlighted in updated answer
    – Tetsujin
    Oct 12 '15 at 6:28
  • 1
    ImageCapture version 6.7 (OSX 10.11) does not have the delete button which is what brought me here. I just read a blog post where the author claims that Apple wants us to migrate to using their cloud service rather than direct import. I hope it's not the case because I don't want to be forced to depend on a cloud service.
    – user391339
    Jan 9 '16 at 13:33

i noticed that the 'delete upon import' option does not show when plugging in an iphone to a new computer for the first time. a simply eject and reopen seems to fix this

i just ran into this problem with both my partner and i

  • Are you running El Capitan (10.11?) I am having this same issue. I am used to both the delete button and delete upon import option.
    – user391339
    Jan 9 '16 at 13:35
  • Yes I'm on 10.11 and the delete option has become available
    – austin
    Jan 9 '16 at 21:07
  • Interesting. It didn't work for me. Just curious can you check which version of Image Capture you are running (in About Image Capture)? Mine says "Version 6.7 (604)".
    – user391339
    Jan 9 '16 at 21:31
  • I saw this behavior as well. Plugging in iPhone for the first time (trust, don't trust dialog comes up) for some reason hides the button. Replugging the phone showed it.
    – Xealot
    May 30 '16 at 19:54

Your workaround #1 is probably simplest if the photos you’ve already imported are interspersed throughout your camera roll. Full instructions:

  1. In Photos, check the “Delete items after import” box on the import page
  2. Select all the photos in the Already imported section, and import them
  3. Open the “Last Import” album, select all the items, and delete them

Delete items after import checkbox

In step 2, you’re creating duplicates of all the previously imported items. In step 3, you are deleting all those duplicates. Meanwhile, step 2 deleted all the items off your iPhone.

If you don’t see the “Delete items after import” checkbox, refer to Austin’s advice to unplug/replug your device, or restart the app. Also this answer only applies if you do not use iCloud Photos - I don’t know what the particulars are, but it sounds like using that service complicates matters.

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