From your description it seems that you are importing books from Kindle for PC into calibre and then later sending them from calibre out to a Kindle device.
Kindle DRM is specific to each app or device and books cannot just be copied from one to another even if they belong to the same Amazon account. DRM removal is needed to make that possible, so it is likely that something is going wrong with DRM removal during import of the books into calibre.
Assistance with DRM removal is not allowed here on MobileRead. I suggest asking for help at either Apprentice Alf's Blog or Apprentice Harper's GitHub.
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