You need to turn on the option to preserve file descriptions when copying files if you want that to happen.
It'll happen anyway for some file formats (where the description can be stored in the file itself instead of a separate metadata stream), or when moving/renaming files rather than creating copies of them, but it's needed in some situations.
There will also be filesystems that cannot store the metadata, where it cannot be preserved when copying to them. E.g. Almost no archive formats support it, and many non-Windows NAS devices don't either.
Also, please Ask one question per thread