Admins aren't privledged users in Phabricator, they must adhere to the same policies you've set for any normal user.

Where are you drag and dropping an image onto, specifically?

Hey Chad, thanks for the response.

I'm dragging the images + files onto the text editing boxes, exactly like this comment section here.

Just to clarify the first comment of yours, that's exactly the issue. I was hoping setting the policy would let me not have to manually set files to visible for all users, but it doesn't affect admin accounts I see.

Could this possibly be related to the intended punch through nature of edge policy relationships between files and tasks. I believe when a file is dropped on an issue as the upload mechanism it is a non-default case, and the intended relationship is that policy is more or less inherited from the task. As an example, I upload file.jpg to a task about sensitive things. It will be set as viewable by me, but the file association tab in files app shows the task association and anyone who can view the task can view the file. It is slightly implicit but quite sane for managing policy relationships between applications. In contrast, if I go to the files app and upload a file directly it inherets the default policy of that application only. This is my understanding of the process :). So if you drag a file onto an issue and the issue is set to all users it is essentially available to all users by association.

As @chasemp discusses, this is intended behavior:

• Uploading a file by dropping it onto the home page, or via Files → Upload File will respect the default policy (drag-and-drop) or default to the default policy (file upload).
• Uploading a file by dropping it into an object's comment box (like a task) will make it visible to users who can see the object and to the uploader, but not to users who can not see the object.
• Other file uploads (like profile pictures, Pholio, macros) have special rules which generally make sense in context (for example: all users can see profile pictures).

In particular, if you go to the file page (/Fxxxx) and click "Attached", you can see all the objects a file is attached to. Any user who can see at least one of these objects can see the file. If you click the policy descriptor in the header (under the file name), you'll get an explanation, which includes this:

Files attached to objects are visible to users who can view those objects.

Are you seeing behavior other than what is described above?

Generally, what actual problem are you encountering? That is, what are you trying to do that isn't working?

Wiki pages had been broken for a while. So if you haven't updated in the past month or maybe two there might have been a old issue you were seeing.