Relinking multiple images in same illustrator document NOT WORKING!

I have been having this problem ever since the update to, i believe either Catalina or Sequoia. I create files with the same jpg image linked multiple times to the same illustration. What i used to do when i needed to link a different file was hide the original file. A window would then come up asking if i wanted to link them one at a time or "relink all", which is what i would always choose. Now with the upgrade i have to navigate to the folder where the new linked file is, and double click on it many many times until all the jpgs are relinked. Sometimes over 40 freaking times! Nothing i've read in these posts has helped and i'm wondering why the heck would Adobe take away a feature that was used and available for years and years, with no workaround! I've been using Illustrator since version 2.5 (somewhere around 30 years!) and have never been so frustrated with this software!  PLEASE HELP!