As always in life: It depends…
Inspect the file names of those items. If they’re named unclear or ambiguous, matching may fail. or they may appear under a completely wrong movie name or may appear as duplicate versions of other movies in the library.
A wholly different approach would be to copy the primary database file again from the NAS and then edit it directly. Thus replacing all the Linux-style path names with their Windows counterparts.
This would ensure that every item would keep its original matching. But it is much more involved and requires some knowledge of SQL: [HowTo] Plex database modification - Moving media the right/wrong way - #10 by jelwell
