At times, instructors and students have trouble uploading files into Blackboard. Normally, this error is caused by the creation of illegal filenames. In fact, MOST systems have trouble with special characters or symbols in the filename, or exceptionally long filenames. Examples of illegal filenames are as such:
 
     * periods.do.not.work.well.at.all.in.a.file.name.doc
     * This-doesNot-work_well-either.doc
     * Some Systems Have trouble with spaces.doc
     * Adding-creative-dates1-12-2007.doc
 
 The best way to create a legal and meaningful filename is to use this naming convention:
 
     * MyWork.doc
     * HomeworkI.xls
     * QuizAnswersI.doc
 
 The *.doc is a file extension. In this particular case *.doc is a Microsoft Word document, where *.xls is a Microsoft Excel spreadsheet, *.ppt is a MS Powerpoint, etc, etc.

Another common cause is corrupted cache/cookies.  Clearing the browser's cache and cookies often fixes the issue -- https://www.wikihow.com/Clear-Cache-and-Cookies