OS: Windows 10
InDesign Version: 14.0.3
Folder: Our folders are saved on Dropbox using desktop app
Who has the problem: My whole team at work.

My team runs static banner ads in automotive. The auto brands have event logos each month. We have several vehicles in running. Each file contains one vehicle and five different ad sizes. To update the logos faster we have them linked to a single InDesign file. That way we only have to relink the logo images in the one file. On original setup the links naturally are direct links, but since we archive each month and copy them over to the new month it breaks the direct links and InDesign auto finds new local links by searching the folder the files are in. I had done this a year ago and was training everyone in on how to do it. When we got to the second month in we noticed InDesign had recognized had properly search in the local folder and even relinked without any notification to us but the problem was it wasn't actually updating the logos. The path was right in the other files leading to the main file we made the changes to for updating the logos but the logos weren't actually updating in the files. The only way to get them to show properly was to manually re-link to the one file they are all attached to. This didn't occur every single time but it did occur most of the time.

Note: The logos are in all kinds of formats but we never change the container box size in InDesign.