Hello there, RockTheTrumpet.
It sounds like you're having issues with importing a particular set of photos from your iPhone's Camera Roll into Photos for Mac. The following Knowledge Base article offers a few recommendations to try:
If you can't import photos from your iPhone, iPad, or iPod touch to your computer - Apple Support
If you enabled iCloud Photo Library on your Mac and iOS device, your photos might already be on your computer. Use these steps to check for your photos in Photos for OS X. You can also go to iCloud.com and open the Photos app to see your entire photo library and choose which photos to import.
You can also use My Photo Stream to access your photos on your computer.
- Check for updates to your photo-management software and iTunes.
- Update your iPhone, iPad, or iPod touch.
- Update your Mac or PC. In Windows, use the Windows Update application.
First, try the steps to import the photos to your computer again. Then try these steps:
- Create a new photo to import. You can save a screenshot on your iOS device by pressing the Home button and the Sleep/Wake button at the same time.
- Connect your iOS device to your computer.
- Try to import your photos again using your photo-management software. You can also try these steps on your PC:
- Mac: Open Image Capture in the Applications folder.
- Windows 8: Move the cursor to the upper-right corner, click the magnifying glass, enter Computer, and press Return. Right-click your device under Portable Devices (if present) and choose Import Photos.
- Windows 7: Choose Start > Computer. Under Portable Devices, right-click the device and choose Import Photos.
- If your computer doesn't see your device, make sure your device trusts the computer.
If you don't see the camera entry in the Device Manager, test your iOS device on a different computer.
Thanks for being a part of Apple Support Communities.
Cheers.