Hi there @sbrooks1375,
Thanks for reporting this, and sorry for the trouble!
Can you tell me more about the errors you got? If you right-click with your mouse and select “Inspect”, what do you see in the “Console” tab?
Can you also share more details about the videos failing to upload, for example, their size and file format?
Have you tried adding a video with a different file format and smaller in size to see if it gets uploaded?
Can you confirm that you’re uploading your videos via WordPress.com? You can do that here: https://wordpress.com/media/yoursiteurl
Uploading the videos to the media library via WordPress.com tends to be more successful. You can upload videos via the WP Admin, but we don’t recommend this method because your host may have upload limits in place that will prevent the video from being processed.
You can learn how to upload to Jetpack VideoPress via WordPress.com can be found here.
All this information will help me better assess your issue and go ahead with the investigation ??
Lastly, could you please post your site URL here so that we can have a look? If you want it to remain private, you can also contact us via contact form. If you choose to reach out directly, please include a link to this thread.
Hope that’s all clear! Let me know what you find out.
