I'm not sure what you mean? I'm just a tech illustrator working mostly in Adobe Illustrator.
In the past, working for various agencies, whenever something like this went down we called in the IT guys within the company, and let them figure it all out. I got up out of the chair, and they sat down and did their thing to fix the problem. I don't have that luxury now working from home. I was warned not to do a system upgrade, but thought it would be painless and easy..."Just upgrade, press the button and voila!" You'd think after all these years that Apple would make this stuff easy for anyone to do. Not so.
This problem is happening randomly with different files and folders when I go to throw them away. Some go into the Trash without login prompts, and some don't.
Explain to me how to check permissions in files and folders for a dummy, LOL. Tell me what I'm supposed to look for, and how to change it if need be...but explain it in very simple terms. I'm NOT a tech guy, I'm an artist.