Add media intermittent error

Hi, I run a book review blog so I post multiple times each day and each post are heavy with images.

I get a regular issue where you are trying to add media to the post. Hitting the add media bring up a pop up screen as usual where you can upload or drag your photos in and sometimes even when the image you just added to your media library is showing and selected it wont let it be added to the post. I have to hit the escape button to get rid of the pop-up window and save the draft post then re go into the media library and add the image that I had previously uploaded. This issue does seem to matter about image size, big or small it happens often. It gets annoying if images wont post repeatedly across multiple posts.

This has been an issue for several versions of WordPress for me at least. I dont get any error messages when this happens

Any idea what could be causing it and any workaround suggestions?