Is the filename in your library in Calibre the same each time?
First, Calibre libraries include one set of metadata, the individual files may include another. You can select the items or select all, and "embed metadata" in Calibre to sync the file's metadata with the library's.
Second, there are export options under tweaks to change how Calibre names files when it exports them.
Third, there's always the possibility of exporting to a tranfer folder on your computer, renaming them there, and sideloading them to your Kindle.
I hope one of these things helps.
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