Good afternoon jbensman,
Welcome to the Apple Support Communities!
It sounds like you are having issues transferring photos to your Windows PC from your iPhone 11 Pro.
iOS 14.0.1 was released on Sept 24, the day after you posted this message.
Let's try quitting the Photos app and updating your iPhone.
How to force an app to close on your iPhone, iPad, or iPod touch
Update your iPhone, iPad, or iPod touch
Then, restart your iPhone to refresh it and reestablish a connection to the internet.
What version of the Windows operating system do you have on your PC?
Make your you have the most recent version of iTunes, and restart your computer:
Update to the latest version of iTunes
After the computer has restarted, try transferring the photos again:
Transfer photos and videos from your iPhone, iPad, or iPod touch
If the issue persists, you may need to remove iTunes and related software, then reinstall it.
Remove and reinstall iTunes and related software components for Windows 7 and later.
Using HEIF or HEVC media on Apple devices
"You can set these devices to capture media using the older formats, which are more broadly compatible with other devices and operating systems:
- Go to Settings > Camera.
- Tap Formats.
- Tap Most Compatible. This setting is available only on devices that can capture media in HEIF or HEVC format, and only when using iOS 11 or later.
- All new photos and videos will now use JPEG or H.264 format."
Settings > Photos > Automatic
This will automatically transfer photos and videos in a compatible format like JPEG (photos) or H.264 (videos) for your Windows OS.
If the issue persists, please reply back to this thread and we'll do our best to help you!
Take care.
