Check and set permissions on the Synology NAS. It is not common, but Synology NAS have been know to mess up access permissions occasionally.
There is an SMB bug in MacOS causing Plex to not find all media files. The missing files are not tied to a certain date, but you might still be affected.
See Plex Files Unavailable but they’re not missing - #638 by Bat_Mang.
In Plex Media Server Settings → Library, enable Scan My Library Automatically then restart PMS.
At startup, Plex will write to the log files the media directories it scans.
Look in Plex Media Server.log and its rollovers, .1.log to .5.log.
Edit: Here’s some sample log entries. This is from Plex running on a Synology NAS. The log files from a Mac should be similar.
Plex Startup
When Plex Media Server starts, it rolls over the log files (they also rollover when they hit a size limit).
BPQ: [Idle] -> [Starting] at the top of a Plex Media Server.log (or .x.log) file is an easy way to tell when Plex Media Server was started.
Jul 28, 2025 13:54:56.734 [140448255281976] INFO - Plex Media Server v1.41.9.9961-46083195d - Synology DS918+ x86_64 - build: linux-x86_64 synology-dsm72 - GMT -05:00
Jul 28, 2025 13:54:56.735 [140448255281976] INFO - Linux version: DSM 7.2.2.72806-3, language: en-US
Jul 28, 2025 13:54:56.735 [140448255281976] INFO - Processor: 4-core Intel(R) Celeron(R) CPU J3455 @ 1.50GHz
Jul 28, 2025 13:54:56.735 [140448255281976] INFO - Compiler is - Clang 11.0.1 (https://plex.tv 9b997da8e5b47bdb4a9425b3a3b290be393b4b1f)
Jul 28, 2025 13:54:56.735 [140448255281976] INFO - /volume1/@appstore/PlexMediaServer/Plex Media Server
Jul 28, 2025 13:54:56.077 [140448257870480] DEBUG - BPQ: [Idle] -> [Starting]
List of folders which have been added to Plex libraries. Search for LibraryUpdateManager.
Jul 28, 2025 13:55:08.536 [140448216017720] DEBUG - LibraryUpdateManager will start watching /volume1/media/tv
Jul 28, 2025 13:55:08.536 [140448216017720] DEBUG - LibraryUpdateManager will start watching /volume2/media2/tv-4k
Jul 28, 2025 13:55:08.536 [140448216017720] DEBUG - LibraryUpdateManager will start watching /volume2/media2/tv-scifi
Further down the log file you’ll see the folders for each movie/show/music/etc. folder that Plex Media Server is watching. Search for [Notify] or [Now watching].
Jul 28, 2025 13:55:33.551 [140448155458360] DEBUG - [Notify] Now watching "/volume1/media/tv/The Beverly Hillbillies (1962)"
Jul 28, 2025 13:55:33.552 [140448155458360] DEBUG - [Notify] Now watching "/volume1/media/tv/The Beverly Hillbillies (1962)/Season 01"
Jul 28, 2025 13:55:33.553 [140448155458360] DEBUG - [Notify] Now watching "/volume1/media/tv/The Beverly Hillbillies (1962)/Season 02"
Jul 28, 2025 13:55:33.560 [140448155458360] DEBUG - [Notify] Now watching "/volume1/media/tv/The Munsters (1964)"
Jul 28, 2025 13:55:33.561 [140448155458360] DEBUG - [Notify] Now watching "/volume1/media/tv/The Munsters (1964)/Season 00"
Jul 28, 2025 13:55:33.574 [140448155458360] DEBUG - [Notify] Now watching "/volume1/media/tv/The Munsters (1964)/Season 01"