macOS 27.0.1 file delete issue

Since restarting your Mac did not help, see if the problem is present when you boot in safe mode. That process performs some system cleanup and clears caches, and also disables 3rd party extensions that may cause problems.

Start up your Mac in safe mode - Apple Support

Create a new file, then delete it and see what happens.

If that does not correct the issue, test in a new user account. A newly-created user account will have all settings at default, and if the issue does not occur in that new account then it provides guidance on what may need to be changed to correct the issue.

Add a user or group on Mac - Apple Support

Once the testing is complete, the new account can easily be deleted.

Delete a user or group on Mac – Apple Support

Those steps will help to isolate the problem.

It might help to download and run EtreCheck, written by a long-time forum member. The free version is fine. Post the full report using the Additional Text button. No personal information is revealed. 

22Liam22 wrote:

That said, are there some permissions that the “Choose Files to Upload” dialog (or Outlook) does not have, and why has this function changed with the release of the new macOS 27.0.1?

To be clear, since this issue affects but not me (and this is the first report I've seen on 27.0.1 of this), the issue does not appear to be generic to the 27.0.1 update, but rather to your Mac.

I would recommend running Disk First Aid on your internal drive.

How to repair a Mac storage device with Disk Utility - Apple Support

As an updated and as suspected, when macOS 27.2 replaced macOS 27.0.1, the issue related to deleting files from within the dialog "Choose Files to Upload" was resolved.

As an updated and as suspected, when macOS 27.2 replaced macOS 27.0.1, the issue related to deleting files from within the dialog "Choose Files to Upload" was resolved.

As an updated and as suspected, when macOS 27.2 replaced macOS 27.0.1, the issue related to deleting files from within the dialog "Choose Files to Upload" was resolved.

Have you done a shut down and then logged in? Sounds like you are deleting as system administrator for a user not signed in which user is normally you. Under the Apple dropdown menu it is possible to sign yourself out and not shut down. Never done myself, but try and make sure you are signed in as user.

Thanks for the suggestion, and yes, even after the macOS 27.0.1 install, I shut down and restarted. Unfortunately, the issue persists. Note: I am the only user on the system, and I always log in as the Admin. Thus, all files are created by me. For example, as a Professor, I create simple text files when responding to my students with their student ID as the file name. And once I am done creating my feedback, I double check it, post it, and then delete the text (moving to the next student). So, the files that are most often deleted are simple text files created and deleted in a desktop "Feedback" folder.

Thanks for the assist, but this issue persists. That said, as I try to identify specific issues associated with deleting basic files, here's a description of one of the cases:

I used to be able to run Microsoft Outlook, select “Attach a file to this item” and then “Browse this computer”, where I would be presented with the dialog “Choose Files to Upload”. And if I wanted to delete a file shown in the dialog, I could do it without issue. However, since installing macOS 27.0.1, when I try to delete a file, I am asked for a password. And no matter how many times I enter the password and try to delete the file, I cannot accomplish the task. Note: The only way to delete the desired file is to launch Finder, navigate to the appropriate folder (e.g., "Downloads"), and delete the file with the admin password (and 'yes' I am logged in as the admin). That said, are there some permissions that the “Choose Files to Upload” dialog (or Outlook) does not have, and why has this function changed with the release of the new macOS 27.0.1?

Thanks for any ideas or insight.

I appreciate your reply, even though the sentence structure was not entirely clear. That said, as a person with a Ph.D. in Technology Integration and an MS in IT, I am comfortable diagnosing issues/errors and determining system release problems. Accordingly, there is no further need for you to respond to my posts, as I will pursue answers from others who are more familiar with this issue and can offer more than basic suggestions.

Thanks