Due to a DC bug, replaced assets doesn't always prompt the "update links" dialog
Sometimes the replace functionality removes the publication to CCC. The CCC can then not see that the links have been updated, and will therefore not prompt the update message.
In some cases, however, you'll still be able to make it "high-res" which then just returns the new image, which the connector didn't have access to (Same environment, same user, two different computers, one returned the new image - the other didn't)
This is (most likely) due to this bug in DC 4.9.1: - DAM-2621Getting issue details... STATUS
The bug should have been fixed for 4.10.0.
Here's the original task I made - it's been put into won't do: