Images placed in Ai file do not show when the Ai file is placed in Ps?

I am a package designer working on a presentation. The past week or so, I’ve been having issues where a package image doesn’t show up when its Ai file is placed in Ps. In order to keep my presentation Ai files as small as possible, the placed images are PNGs, sometimes JPG, but I prefer the transparency of the PNG. (Not sure if that’s relevant, but possibly.)

In my workflow, I start by making label layouts in Ai on the supplied dieline. In another Ai file, for the presentation, I place my layouts on top of images of, let’s say a bottle of cranberry juice, to simulate what my label would look like on the bottle, and save the presentation file. To make a shelf render (a picture of the new cranberry juice label on shelf in the store), I place the appropriate page, linked, from my presentation document into an image in Ps, masking out the unneeded content. Then I place that PSD file into the presentation file. Then save the presentation file, and make it a PDF for distribution to the appropriate parties. 

TLDR: layout file > placed into presentation Ai file > placed into PSD file > PSD placed into presentation Ai > Presentation file saved as PDF for distribution. All files are saved with PDF Compatibility turned on. See attachment for a visual of this.

Everything is linked so that if I make a change in my layout file, I only have to update the links in the subsequent files. This has been working very efficiently for me for years. I love that I don’t have to update concepts manually when they are in my presentation file multiple times. just update the links.

As I said earlier, I’ve been having issues lately where the package image doesn’t show up when its Ai file is placed in Ps. Is this a bug, or something with saving Ai with PDF Compatibility, or ?? Any thoughts are appreciated, I’m stumped for a fix. 

Ai 30.2.1, Mac OS 26.3, MBP M3 Max with 64 GB RAM. 

Thanks!