There are various ways to upload and insert images and files, but ways shown here is considered as the most effective way to upload and insert materials in the course.
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Uploading images/icons/course files
It is recommended that you go to your own "Files" section to upload everything you need in the course. You can upload images and files spontaneously within the course, but you will not be able to multi-select your files to upload.
Make sure you click on your course folder to upload images/files. Otherwise, you will not see any images/files in your course when inserting.