My immediate suspicion is that Plex is adding one of the movies as a “duplicate” of another movie. Some Bond movies have similar/identical names as other movies, so if you do not follow proper naming conventions (including release year), Plex may mis-identify one of the movies as another. (For reference, the Naming and Organizing your Movie files article)
However, even with the proper year, Plex still seems to mis-identify a file every now and then. In particular, Casino Royale, despite having the years, the new one might be incorrectly scanned by Plex as a duplicate of the original older movie. So to check, put the bond movie into the folder with the rest, and do a scan. Then, check for duplicates.
To do so:
- Enter the movie library’s “Library” view.
- In the upper left, change the sort method from “All” to “Duplicates”.
- See if one Plex thinks you have a duplicate.
- If you do, click the triple dot
...menu and pick “Split Apart”. - Find the separated files, then click
...and do “Get Info” to identify which file is which. - For the one marked as the wrong year, click
...and pick “Fix Match…” to pick the correct version.
If it’s not a duplicate… well, I dunno. Do a plex dance on the movie to really clear it out of the library, add it in, do a scan, then check your server logs to see if the logs explain why it won’t get picked up.