I have a folder containing 18 FLAC audio files. When I copy the entire folder to OneDrive, 12 files transfer normally, but 6 are skipped. If I copy those six files individually, OneDrive renames them using an old 8.3-style filename and changes the extension—for example, "09 Shock me.flac" becomes "09SHOC~1.FLA." Dragging and dropping and using OneDrive's file-upload option produce the same result. I've restarted the computer, compared the files and their metadata in Mp3tag, and checked their properties, but I can't find any difference. What could cause this, and how can I upload the files without them being renamed or skipped?
2 Answers
Compare a checksum or hash of the original files with anything that appears in OneDrive so you can tell whether the contents changed or only the displayed name did. Also verify that the files are genuinely FLAC files rather than files with a misleading extension. Try opening each one in a player such as VLC and inspect the full filename and file type in Windows. The .FLA extension was historically associated with Flash source files, so it’s worth ruling out an incorrect extension or unusual file metadata.
The shortened name looks like the old DOS 8.3 filename format, so something in the copy or upload path may be treating these files as legacy filenames. Check whether the problem occurs only in a particular folder or destination, and look for an error message from OneDrive. It would also help to confirm how the files are being copied, although both drag-and-drop and the upload command appear to give you the same result here.
I’ve tried both drag-and-drop and OneDrive’s upload-files option. Twelve of the 18 files transfer normally, while the same six are renamed or skipped.

I’m not sure how to check a hash, especially for the versions shown in OneDrive. I’ve already compared the properties and tags of the files, but nothing obvious differs.