Remove item and image from a list

I have a DB that I has a field of type List of files. I have a button that is supposed to Delete the file, image from the DB and the image from the file manager. Everything works with the following setup with the exception of removing the file. The image is removed from the DB record and the image is removed from the File Manager. Can someone please explain why the file would not be removed please?

Below you see an image where I have ran the delete workflows which did delete the image but left the file:

If you add the delete button in the repeating group in the form of a trash icon or something then you will not have to save it as a state and can simply say remove “current cell’s file”. I am thinking maybe as soon as the image is removed then you lose access to reference that anymore as something to delete but if you say Current Cell’s file then it may work?

I tried that but unfortunately have the same results.

The good news is that the picture is delete from the Randolm Pictures (image) field with either option therefore it works in the clients view but it leaves behind information that is not accurate in the Random Pictures (file) field and the file in the File Manager.

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