Hello @displaced7,
I understand your frustration with the issue you're facing when updating images and their duplicates in Adobe Illustrator. It's definitely frustrating when software behavior doesn't align with your expectations, especially when it involves time-consuming processes.
It seems like the issue you described might be related to a known problem. If it's similar to the issue mentioned in this UserVoice thread (https://illustrator.uservoice.com/forums/601447-illustrator-desktop-bugs/suggestions/47070262--repla), I'd like to let you know that our team is actively addressing this problem. The issue has been resolved in the public beta version 27.10.215, which is a positive indication that it will likely be fixed in the next general release of Illustrator as well.
Your feedback is important in guiding our development efforts. To ensure that your input is taken into consideration, I recommend upvoting the related UserVoice entry and adding your comments, especially after you've had a chance to test the fix in the beta version. This helps us understand the issue's impact and the solution's effectiveness.
Thank you for sharing your feedback and patience as we work on resolving this issue.
Best regards,
Anshul Saini