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When backend user want to replace existing image file,there is a way like this:
Click insert image to go to file manager UI,then find the target file and select it,then click delete button,then upload new file.
When i want to produce a page,create or update or both,it may need to replace some files for many times,i can feel that this is not a happy job,file manager was helpless.
My suggestion is,provide user some options to choose,maybe like these:replace(all),rename,cancel,like most OS do.