macOS: Keeper Trash
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Moving Files to Trash on macOS — Keeper Trash
Platform: macOS only
What is Keeper Trash?
Keeper Trash is a small app that adds a policy-aware path to your Mac's Trash. When your organization has set up access controls on certain files or folders, moving them to Trash through Finder won't work — those actions are governed by your organization's security policies. Keeper Trash is how you do that correctly.
It looks and behaves just like normal macOS Trash, with one difference: before the item is moved, Keeper may ask you to confirm your identity or provide a reason. Once that's done, the item lands in your Trash just as you'd expect.
Keeper Privilege Manager must be running on your Mac for Keeper Trash to work. Your IT team handles the installation — you don't need to set anything up.
Four Ways to Move a File to Trash
Pick whichever method fits how you're already working. They all go through the same process behind the scenes.
Right-click in Finder
This is the most familiar approach if you're already browsing in Finder.
Select the file or folder you want to move.
Right-click (or Control-click) on it.
Look for Move to Trash with Keeper… in the menu. On some macOS versions it may be tucked inside a Services or Quick Actions submenu.
Click it and follow any prompts that appear.
Finder Menu Bar
If you prefer using the menu bar:
Select the file or folder in Finder.
Click Finder in the menu bar at the top of your screen.
Choose Services → Move to Trash with Keeper…
Drag onto the Keeper Trash icon in your Dock
If Keeper Trash is visible in your Dock, you can drag files straight onto it — no windows or menus needed.
In Finder, select the file or folder.
Drag it onto the Keeper Trash icon in the Dock.
Release it there and follow any prompts.
Keeper Trash doesn't need to be open or in the foreground for this to work. As long as it's running in the background, the Dock icon will accept drops.
Drag into the Keeper Trash window
If you prefer dragging into a window:
Click the Keeper Trash icon in your Dock to open its window.
Drag files or folders from Finder directly into that window.
Follow any prompts that appear.
What Happens After You Start a Move
Once you've initiated the move using any of the methods above, Keeper checks your organization's policies for that item. What happens next depends on what your IT team has configured.
In many cases, nothing extra is required — the item moves straight to Trash and you'll see standard macOS Trash behavior. There's no separate "success" notification from Keeper Trash itself; your Mac's Trash simply gains the item.
If your organization's policy requires a step from you, one of the following prompts will appear:
Justification — A dialog asking you to type a brief reason. Write a short description of why you need to move the item and click Submit. If you close or cancel the dialog without submitting, the move will not complete.
Multi-Factor Authentication — A dialog asking for your email or username and a six-digit code from your authenticator app. Enter both and click Submit. If you enter the wrong code too many times in a row, you'll be temporarily locked out — the dialog will tell you how long to wait before trying again.
Approval — A dialog asking you to confirm that you'd like to submit a request. Your request will be sent to an approver at your organization (usually your manager or IT administrator). The move won't complete until they approve it. You'll receive a notification once they've responded.
Finishing a Move After It's Been Approved
If your request needed approval, the move doesn't complete automatically once your approver says yes. You'll need to take one more step to complete it.
Open KeeperAgent — you should see it in your Dock or be able to find it in your Applications folder. Inside KeeperAgent, look for your approved request and follow the steps shown to complete the move to Trash.
Your IT team may also have trained you on a specific way to do this — follow those instructions if they differ from the above.
A Few Things to Know
Only one item at a time. If you select several files and use Keeper Trash, only the first item in the selection will be processed. The rest will stay where they are. Move them one at a time, or use regular Finder Trash for items that don't require Keeper.
Where Keeper Trash works. Keeper Trash is designed for typical user and application locations: your home folder and everything inside it, the Applications folder, external drives and volumes, and system application folders. If you try to move something from a location outside these areas, Keeper's policy engine may deny the request.
No separate pop-up for success. After a move completes, you won't see a confirmation window from Keeper Trash. Your Mac's Trash will simply contain the item — that's the confirmation.
If Something Isn't Working
"Move to Trash with Keeper…" doesn't appear in the right-click menu or Services menu
First, check that Keeper Trash is running — look for its icon in the Dock or ask your IT team to confirm it's installed. If it's installed but the menu item still doesn't show, try these steps:
Go to System Settings → Keyboard → Keyboard Shortcuts → Services and check that the Keeper Trash service is enabled.
Quit and reopen Finder: hold Option, right-click the Finder icon in the Dock, and choose Relaunch.
If you've just had Keeper Trash installed, a log out and back in may be needed the first time.
I chose the option but nothing happened
Check that Keeper Privilege Manager is running — your IT team can confirm this. Also make sure Keeper Trash isn't being blocked by security software. If you've never opened Keeper Trash before, try clicking it once in your Applications folder to let macOS register it, then try the move again.
I had my request approved but the file still hasn't moved
This is expected — see the Finishing a Move After It's Been Approved section above. Use KeeperAgent to complete the move.
Something else is wrong
Contact your IT helpdesk. Provide them with the name of the file you were trying to move and what happened (or didn't happen) when you tried. They can check the logs on your machine to see exactly what occurred.
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