I finally found the answer to a frustration I’ve had for a while. When you copy multiple files in Windows Explorer the file you click on when you begin the drag is the file that is copied first. It copies all the files below it that are highlighted and then starts at the top of the list. This also applies to right-clicking to affect multiple files. It happened most often to me when playing/enqueuing stuff in Winamp. I would select files, right-click and select enqueue in winamp. It would add them to the playlist, but not sorted correctly. If you right-click on the first file, then it brings them in in the order shown. Do others know of this? I’m surprised I never noticed it before.
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