We then selected the oldest half by finding the rough middle point and selecting from there backwards in time. With Image Capture, we attached her phone to her Mac via USB, selected it in the app, and then used the Date field to sort images in chronological order. Connecting your iPhone to your Mac with a USB cable may be the easiest way to transfer photos from your phone to your computer, but it isn't the only way. The Photos app on my mac is not importing the photos from my iPhone when connected with USB-Lightning connector. This lets you drill down to the problem, while also accomplishing the task (like importing media) for sections of the overall set you’re working on.
To figure out what the cause of the problem was, I suggested a different tactic: binary troubleshooting, which is where you split a set of whatever you’re working in half, try to accomplish an action and, if it fails, split it in half repeatedly. (She has an encrypted online backup and regular clones of her drives, to ensure we don’t lose her Photos library.) Connect your iPhone, iPad, iPod touch, or digital camera to your Mac with a USB cable. These steps also work for importing images from digital cameras and SD cards. The list of failed imports was so long, it didn’t seem worth the time to try to run each of those down, and she lacked the confidence that her originals were imported correctly besides them that would lead her to delete them from the phone. You can use Photos for OS X to import photos from your iOS device to your Mac without using iCloud Photo Library.
After your selection has been made, click Open option as a confirmation to transfer the photos to the iPhone. You can either import the photos from Mac one by one or import the photo folder in 1 click. Image Capture can import images, but also helps you troubleshoot import problems. Simply select the add photos option that will be available at the top of the screen. (To remove Photos duplicates, the best option appears to be PowerPhotos, which can work with Photos libraries directly for deduplication, merging, and other features.) IDG Image Capture doesn’t have an option like Photos for importing only new images (ones that it’s sure it imported before), but it also didn’t seem like there were rampant duplicates. She tried to import all images, and it would appear to make progress, but then fail with a lengthy error message listing problematic images, and an incomplete state of what was imported. In my wife’s case, however, Image Capture stopped working.
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