fiona86

Does your site health page report any issues that need to be addressed?
– No critcal issues. Just some recommendation like removing of inactive plugins and themes.

Are there any errors logged in you browser console after you attempt to insert media?
– There is no error message when I try to insert image from the Gallery Pop-up. However, if I try to copy+paste an image in the editor and try to upload, there is no way I could publish the update. It will direct my to an error page that says “Oops! That page can’t be found. Nothing was found at this location. Try searching, or check out the links below.”

Are there any errors logged in you browser console after you attempt to insert media?
– No error message will appear.

@bcworkz If you have view the videos I included in my post, you will know I created a fresh new WordPress installation specially to test on this issue. That new wordpress site has no third party plugins. This is a new video that I took to show you it’s really a new site with no third party plugin: https://thedailymedley.com/wp-content/uploads/2020/12/VID_20201221_101223.mp4

The old site of mine that runs on WordPress 5.53 has much more plugins and yet it is not faced with the issues that I am facing for my site that runs on 5.6.

I only used Storefront theme for all my sites. I had also previously switched to Twenty-Twenty / Twenty-Twenty-One themes but I will still face the same problem

I tried to install Enable jQuery Migrate Helper plugin and it doesn’t help. https://thedailymedley.com/wp-content/uploads/2020/12/VID_20201221_102304.mp4