Delete files without entering a password?

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I have a MacBook Pro running High Sierra 10.13.6 with an SSD main "drive" and a backup hard drive. I want to clean up my drives by deleting unneeded files before upgrading to a new MBP. But I've encountered a problem with my backup drive. I have to enter my login password before I can delete files. This is complicated by my wanting to delete duplicate files by running Duplicate Detective (DD). DD states it deletes files but it really doesn't, probably because MacOS is asking for my login password. Neither Apple techs nor DD support could suggest a solution to me. So I wonder if someone in the Mac community may have encountered this problem and has a solution. Note: I can put backup drive files in a folder, move the folder to my SSD, then delete the folder, which deletes the files. But I cannot delete the files under the moved folder without entering my password. I can't do this manual process because I have too many files to manipulate.
Thanks in advance for any help you can provide.
 
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Why is needing to enter your password a problem? I don't fully understand. Is it necessary to enter the password multiple times?
 

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The only reason you'll need to enter your password is because of the mismatch in ownership of files/folders.

For example, the trash can on your Dock is actually backed up a folder in your home directory called ".Trash", the period before the word makes it a hidden folder. If that folder, somehow, isn't owned by you, then every time you want to delete a file or empty your trash, you'll be asked for your password. Since the first account created is the admin user, you are using Admin privileges to delete the files.

I'm shocked that Apple couldn't help you with this, since it seems like a simple permission issue.

Anyway, please describe, step-by-step, what actions you are taking in Finder with the proper references to drives so that we can follow along. Your description is not easy to follow. Take screenshots to better explain what you are doing/seeing.
 
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Also, what kind of backup are you talking about? If it's Time Machine, tools like DD should NOT be used as what looks like files are actually links in a chain. And if you take out the "duplicate" links, the database that TM uses to build/rebuild from the backup will be corrupted and the backup useless.
 
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Why is needing to enter your password a problem? I don't fully understand. Is it necessary to enter the password multiple times?
Entering a password for a few deletions isn't a problem but it is when hundreds of deletions must be made.
 
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Also, what kind of backup are you talking about? If it's Time Machine, tools like DD should NOT be used as what looks like files are actually links in a chain. And if you take out the "duplicate" links, the database that TM uses to build/rebuild from the backup will be corrupted and the backup useless.
My "backup" drive is the original disk drive that I moved to the bay occupied by a CD/DVD drive, and was intended to be used as additional storage and as a place to store Windows apps and files. SSD replaced the original disk drive. Both of these are internal. Time Machine uses a separate external drive. I'm not trying to manipulate Time Machine files.
 
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The only reason you'll need to enter your password is because of the mismatch in ownership of files/folders. . . .
I'm shocked that Apple couldn't help you with this, since it seems like a simple permission issue.

Permissions were reset on both internal drives, twice. After looking at drive info Apple techs could see no reason why this issue was occurring since I was Admin on both.
Anyway, please describe, step-by-step, what actions you are taking in Finder with the proper references to drives so that we can follow along. Your description is not easy to follow. Take screenshots to better explain what you are doing/seeing.
May take some time to do that. I may try to find another duplicate file finder app that will let me do what Duplicate Detective does not, and that is to put duplicate files I want to delete into a folder on my MBP instead of trying to put the files into Trash. Putting the dupe files into a separate folder will allow me to delete them by deleting the folder, which will also delete the files contained in that folder.
 
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IWT


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@bidwin

I'm sorry to say this, but I think your problem, in addition to what the others have said, is your use of Duplicate Detective.

I know you can download it from the App Store, but my guess is that the way it works, it is not intended to be used on any Backup (BU) Drive - and never, ever, if your BU drive is Time Machine.

We really have to know exactly, step by step, what you did.

We are not sitting beside you watching your every move. Please help us to help you.

Ian
 

Rod


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My "backup" drive is the original disk drive that I moved to the bay occupied by a CD/DVD.

If I understand the above correctly that (now external drive) has your previous MacOS on it and should be bootable. Is that the case or did you erase it before using it as a backup?


Sent from my iPhone using Mac-Forums
 
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Images below are in response to requests for more detail about what I'm trying to do, which, simply, is to be able to delete files from a "backup" disk without entering my login password before deleting them. I used Duplicate Detective to find duplicated files which I will delete before moving all remaining files from my "backup" disk to my SSD after which I plan to remove the "backup" drive. My ultimate objective is to keep relevant files then upgrade to a new MBP. I have no easy way to manually find and delete numerous duplicated files.

Image "01 MBP disk drives" shows the "drives" on my MBP. My MBP was slowing down so I maxed memory to 8GB and replaced the original hard drive with SSD (outlined in red) to extend its life. The original hard drive was moved to the CD/DVD bay and named "WinDisk" (outlined in blue). I only use this drive as storage, NOT as a Time Machine backup drive and NOT as a boot disk. The SSD and hard drive are INTERNAL to my MBP.

An EXTERNAL drive is ONLY used by Time Machine and IS NOT manipulated by Duplicate Detective nor by me (outlined in Magenta).

Image "02 WinDisk files" shows some of the files located on my "WinDisk" drive that I want to delete.

Image "03 Selected WinDisk files" shows files located on my "WinDisk" drive that I have selected to be deleted.

Image "04 Delete WinDisk files" shows files located on my "WinDisk" drive that I am about to delete by clicking "Move to Trash".

Image "05 Dialog Box" shows my MBP displaying a login dialog box which requires my entering my login password before deleting the files selected above. It is this requirement to enter a password that I'm trying to eliminate because I believe it's preventing my using Duplicate Detective to delete duplicated files. Note, I have previously used Duplicate Detective successfully. I am not defending it but just stating that it has worked for me in all cases except when using it to delete files from my "backup" WinDisk drive.

I hope the info above and the images below provide enough detail about what I'm trying to do, but if not please ask questions about what is not clear to you and I will respond.

Again, thanks much for your attention to my issue.
 

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Rod


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Thanks bidwin, thats very clear and your notation is great. You did not mention if the Disk has the original MacOS still on it?
 

IWT


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@bidwin

You have gone to an enormous amount of trouble to help us with pictures and dialogue for which you are to be sincerely congratulated.

If you simply swapped out the old Internal HD and now use it as a backup drive named WinDisk, then, as Rod has mentioned, this should contain the original MacOS and if so, again as Rod said, that would make it bootable.

What's in my mind is that if you booted your Mac from WinDisk, it should be much easier to delete anything you want without having to input your Admin PW. You could then reboot your Mac from the new internal SSD and do what you like with WinDisk.

My reasoning about the repeated need to input your Admin PW when deleting from WinDisk is that your Mac "sees" it as a separate system rather than a simple External Hard Drive.

Ian
 

Rod


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Yes, you have followed my train of thought exactly Ian. If that is the case, although it will be very slow I would suggest the same solution.
bidwin, if you can get everything off the HDD, just temporarily you could erase it and put what you want back. That should remove the problem.
 
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When you swapped the drive to install a new one, and then installed the OS on the new drive, did you use Migration Assistant to create your account on the new system and then migrate your desired data from the old drive, or did you manually create a user account on the new drive? If the latter, even if the name of the account is the same, the system knows that it's a different account from the account of the same name on the other drive. Hence, you are trying to delete a file that is "owned" by a different user and have to prove you have authority to do that by providing an admin password. I also see that in your images it says "shared" folder as the location of these files. Is that location a result of the assistance you received from Apple? Shared folders are the way the macOS allows different users to be able to copy documents. Here is Apple's document on that subject: https://support.apple.com/guide/mac-help/share-files-with-others-who-use-your-mac-mchlp1122/mac

Note that it says:
Files in a user’s Public folder or in the Shared folder can be read by all users of the Mac, but edited or deleted by only the owner of the file. If you want to allow other users to edit those files, you need to change the file permissions. See Change permissions for files, folders, or disks on Mac.
 
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Finally got it to work! Don't know what finally did the trick but read the articles in links MacInWin sent and selected Sharing & Permissions for WinDisk under Finder, highlighted my admin name and selected the action pop-up menu
77dd27f9e7f1275209461fdaf84e1137.png
, then chose “Apply to enclosed items" to my admin name. That let me delete files from WinDisk without entering my login password, but Duplicate Detective (DD) still did not work. I then put DD on WinDisk and ran it from there. Success!

Before doing the above I tried to boot from WinDisk but didn't see WinDisk in the list of drives. Another drive was displayed (can't remember its ID but it was a string of numbers) so I selected that one since I know of no other drives on my MBP. Boot failed. I rebooted from my MBP SSD, everything came back OK.

Thanks all very much for your insights and suggestions. Couldn't have done this without you. You succeeded when Apple did not. (y)
 

Rod


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Thanks for getting back to us bidwin, that's great news, well done.
 

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