"Grey" image boxes causing bug splat

[BTApostolo]

First time posting and I'm not sure where to drop this so starting here.

I'm having issues with image entities that are not loading into my model. I'll have a few different images dropped into my model and at a later date I'll open it and the images will not load but rather show grey boxes in place of the images. I'm using JPEG and PNG specifically and all images are under 800x800 so I can't imagine they are too large.

When my model has the grey boxes, if I try to reload, replace, or import to fix it, it causes a bug splat. I can't determine what is causing this at random but it has been happening for a couple of months sporadically. On one occasion my model turned all the images to grey boxes and at a later date I opened it and they "reloaded" by themselves. I'm not sure if something is de-linking or what.

Thanks in advance for any help!

[TIG]

Have you tried adjusting various combinations for your Graphics Card's settings in SketchUp's Preferences > OpenGL ?
What is the card and what are its settings ?
Has the card's driver updated recently ?
What is your MAC's OS ?
Has that updated recently ?