Hello, Proffit91.
Thanks for getting back to us on this. Sounds like you're using iCloud Drive: iCloud Drive FAQ Have you tried uploading a new/another video to see if the same thing occurs? If you have a backup copy of that video on your PC, try removing the current one and upload it again.
To help you out, have you seen this article about syncing your iPhone? Sync your iPhone, iPad, or iPod using your computer
Using iCloud Photos is a good alternative too. Using iCloud Photos should still allow you to upload your content, you just need to make sure that the video is downloaded on the device: Set up and use iCloud Photos
"Download your photos and videos
You can download a copy of your original photos or videos on iCloud.com, iOS, iPadOS, or Mac.
- On iCloud.com, click Photos, then select the photos and videos that you want to download. Click and hold the download button
in the upper-right corner of the window. If you want to download your content as it was originally captured or imported, choose Unmodified Original. For JPEG or H.264 format — including edits, and even if it was orginally in HEIF or HEVC format — choose Most Compatible. Click download.
Make sure that you have enough storage
The photos and videos that you keep in iCloud Photos use your iCloud storage and your device storage. And as long as you have enough space in iCloud and on your device, you can store as many photos and videos as you like".
If you turn on Optimize Storage, iCloud Photos automatically manages the size of your library on your device. Your original photos and videos are stored in iCloud and space-saving versions are kept on your device. Your library is optimized only when you need space, starting with the photos and videos you access least. You can download the original photos and videos over Wi-Fi or cellular when you need them. You can use Optimize Storage on your iPhone, iPad, iPod touch, and Mac.
If you turn on Download Originals, iCloud Photos keeps your original, full-resolution photos and videos in iCloud and on your device".
Best regards.