Relinking in Adobe Illustrator

Hello I need some help, 

I am currently using Adobe 2024 and V 28.7.5 on Windows 11 - We need to use this because our print software doesnt have the registration marks set up for 2025 quite yet

We create a couple of template files at work with logos placed on different artboards on different items. We have to replace them to reflect the company we are working with. Up until a couple of days ago, I would open the link panel, select multiple links, press relink and one after another file explorer window would pop up so I could replace them all at once essentially. Each time I would select one, the window would close and another file explorer window would pop up.

Yesterday I went to the same template file and selected all of my images I needed to replace and pressed relink though the window only popped up once and only changed one of my selected items and didnt show up again. 

My coworker tried to do multiple links at once and it is still populating the additional windows explorer box to replace image after image but mine stops after only one. 

Is there a setting I accidentally ticked on? Any help is appreciated.