Can't delete files until I put in passoword

Visit The XLab FAQs and read the FAQ on solving Trash issues. You can also try using Trash It! 5.1 to fix the problem. Or you can try this:

Open the Terminal in the Utilities folder and paste the following at the prompt:

sudo rm -Rf ~/.Trash

Press RETURN. Enter your admin password when prompted. It will not echo to the screen. Press RETURN again.

(Should anyone tell you this is dangerous or unnecessary, please ignore the comment.)

Then you may be attempting to delete system files or other files for which you are locked out of access. You will need to try changing the permissions of the file your are trying to delete or determine if you should even delete it.

Are these files located on your Mac or are you accessing it via a network share or some other way?

You may want to confirm the path of the files with us here, if they are system files or files from a Time Machine backup etc you may have issues trying to remove them.

Are you sure that this dupguru tool — I see some open-source named dupeGuru, is that the tool you're working with? — is working and reporting valid data, and not reporting spurious or invalid or incorrect duplicates? (The dupeGuru tool lists a couple of different ways that the tool works, including some sort of a "fuzzy matching algorithm".)

While I'm not familiar with dupguru — or dupeGuru — and the tool may well be working correctly here — some add-on tools have had a history of causing problems and corruptions, unfortunately. If the tool has an error here (if!), then I'd wonder if you're attempting to delete your backups, for instance.

As Drew Reece states, if the files are not somewhere in the /Users/{your short name} path that is your login directory, then you'll want to be extremely cautious about deleting the files.

Without revealing any sensitive data via the filenames, can you post the full paths of some exemplar file pairs?

The problem is we don't know if you have permission to do that & we don't know where the files originated. The system tries to prevent you deleting files that it needs.

You are not answering any of the questions you have been asked, so we are just left hanging…

Have you moved these the files into the trash or are they still somewhere else?

Are these files located on your Mac or are you accessing it via a network share or some other way?

Do you have admin access on this Mac?

You can use various apps to remove files like this and you can gain higher levels of access but it is a risk & we are trying to help you to avoid damaging the OS.

Apologies we seem to be posting at the same time 🙂

Once you have it reinstalled & booting OK…

Try removing the files after the folder with the colon.

e.g. delete the folder inside

users/my name/desktop/ableton/samples/drum rack//kicks/samples:loops/samples

colons are not legal characters & can cause issues in file paths.

You may find Omnidisksweeper to be better…

https://www.omnigroup.com/more/

See Linc Davis's instructions for running the app 'as root'

Apps taking up too much space ???

The key part is quoted below, but read all of his post…

For ODS:

security execute-with-privileges /A*/OmniDiskSweeper.app/*/M*/* 2>&-

You may need to do the thing he mentioned in red text - delete the files as root, just be very very careful (& have a backup).

NOTE: If this 'Server HD' is mounted over the network it will continue to fail, it should be directly attached.

Unix usually has all file systems united, so you might have two physical devices, but you'll have one file system covering both.

Your

users/my name/desktop/ableton/samples/drum rack//kicks/samples:loops/samples/Drum rack/snares

has embedded spaces, which means you'll have to escape those characters or quote the paths.

I'm also not certain whether the double // or the colon is being used as a delimiter? Or is that embedded in the path?

Use the following command to check each of the two files for protection, ownership and status:

ls -ale@ {path}

It's possible that there are links here; that there are two paths to the same file. (I'd wonder if whichever one you're attempting to delete is the canonical and reference copy for the Ableton application, and protected against errant deletions — that'd explain all of what's happening here.)

It would not surprise me to see an audio package store a copy of the sample right in the package, as that would make the resulting audio composition project more portable.

Check with the folks supporting the Ableton audio package, as they'll be able to tell you if there are copies maintained, or if they're using links.

I would not expect much savings from removing samples, either — not without a whole lot of duplication. Audio files just aren't all that big, and they're often compressed. If you do have a lot of data, then bigger disks are a very cheap solution.

It's up to you how to go about it. You can install one of the apps & run that one command I linked to use that app as root, that will remove them all, but does risk doing other damage if you choose to delete the wrong thing.

Another option is to use Terminal to 'rm' the folder as root - but once again that is a risk. The OS tries to protect files & it appears you don't have permission to remove them, so it will require work to deal with that.

One more possibility, try resetting your home folder permissions. It may not help, but it might…

Backup before you begin – just in case.

Boot holding cmd+R. Recovery mode should startup (assuming you have a recovery partition).

Select Terminal from the Utilities menu.

Enter the word…

resetpassword

… & hit return.

The GUI app will open, select the main boot disk.

Select your user account in the popup menu.

Then click the Reset button at the bottom right. It will "Reset Home Folder Permissions & ACL's"

Repeat for the other users.

Quit ResetPassword from the menu,

Quit Terminal

Reboot

Try deleting the files again

The resetpassword tool seems to fail to fix permissions on occasion so the other options would be my first step. Whatever you decide it requires you to do some typing, it's not difficult you just need to take care. It's not clear on how we can help you, to gather more information we would need you to run commands which involves using Terminal…