Attachment won't work after uploaded to LMS

I have atached several files to my course using the attachment feature. All the files open in preview and after I publish. However, when I upload the course to LMS one of the files does not open and I get a "Bad Request" error message. I have removed the file, reinserted, previewed and republished the course. The one file still wil not open and I get the "Bad Request" error message. The original is .ppt file. It would not open at all. I then saved it as .pdf and it opened in preview and publish. When uploaoded in LMS is where I am having trouble.

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