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I have the following file input box that allows for multiple upload:
<input name="filesToUpload[]" id="filesToUpload" type="file" multiple="" />
My users pick their files and they appear in a list. But say after picking their files a user wishes to add more files without overwriting the existing files chosen. Is it possible to add on to the list of existing files or would I need a new file input element?
No, you should make new input element (perhaps by insert a new input element in onclick event handler).
This is reference link from Mozilla Developer about FileList object.