I think the issue is with Dropbox.
Keeping everything in the same Dropbox folder, I created a jpeg and after making changes and saving, it didn’t update similar to the designer file. As soon as i put the files on my desktop and replaced the link with the new files on the desktop they both updated instantly without me having to force an update. Same publisher file, same ‘placed’ files(except for their location.)
i hope this is something that can be addressed at some point, as i have all of my files on Dropbox and save them locally with ‘make available offline’. It’s the way i have worked for quite sometime now and have never had an issue with links in InDesign.
I was planning on switching the office to this over adobe but will now need to see if this is an issue specific to Dropbox or something that will be an issue on a network setup as well.
On a side note, I was having issues with links being lost on the iPad app, but i use Dropbox there too. I am assuming there is something about how Dropbox works that is causing this now.