The recycle bin is usually capped Ata a percentage of your HHD space. You're probably hitting that limit, which will permanently delete files you're trying to put in above that limit. But I have to ask, why are you "storing" important files in the recycle bin? That's not at all what it's for. Answer from CajuNerd on reddit.com
🌐
Reddit
reddit.com › r/windows › "are you sure you want to permanently delete this file?" help?
r/windows on Reddit: "Are you sure you want to permanently delete this file?" help?
June 8, 2018 -

For some reason sometimes, for instance when moving a file from my flash drive to the recycle bin, I get a message that says exactly whats quoted above and rather than storing it in the recycle bin the file is indeed permanently deleted. Recently I did this for a very important document and it was a headache using file recovery software to retrieve it. My question is, how can I disable this from happening in the future so that EVERYTHING I move to the recycling bin stays there until I empty it?

🌐
TrueNAS Community
truenas.com › forums › archives › freenas (legacy software releases) › freenas help & support › storage
Annoying warning: "Are you sure you want to permanently delete this file?" | TrueNAS Community
September 11, 2016 - However if I want to delete files on my NAS, I always have to confirm deleting every single file. Is there any setting that could deactivate that annoying message? Click to expand... Are you selecting all the desired files to delete and then doing a "SHIFT + DEL"? Also, you could get around it via command line instead if needed... ... cyberjock's: Hardware recommendations (read this first) dlavigne's: ZFS Primer cyberjock's: Slideshow explaining VDev, zpool, ZIL and L2ARC for noobs!
Discussions

How to Disable the 'Are you sure you want to permanently ...
Hi! Come and join us at Synology Community. A place to answer all your Synology questions. Ask a question or start a discussion now. More on community.synology.com
🌐 community.synology.com
November 11, 2024
Files not going to recycle bin - Windows 10
In Windows 10, when I delete a file in File Explorer, it says 'Are you sure you want to permanently delete this file' then when I delete it, the file doesn't go to the recycle bin. More on forums.digitalspy.com
🌐 forums.digitalspy.com
May 3, 2022
win11 24h2, disable 'Are you sure you want to permanently delete' dialog on network share?
Making changes to your system BIOS settings or disk setup can cause you to lose data. Always test your data backups before making changes to your PC. For more information please see our FAQ thread: https://www.reddit.com/r/techsupport/comments/q2rns5/windows_11_faq_read_this_first/ I am a bot, and this action was performed automatically. Please contact the moderators of this subreddit if you have any questions or concerns. More on reddit.com
🌐 r/techsupport
4
1
March 22, 2025
How do I stop Finder from giving me a war… - Apple Community
This makes it act as a wired keyboard as will insure a successful boot into Safe Mode. ... It looks as maybe the problem has something to do with Dropbox. If you drag a file from another location, not synced to Dropbox, does it give you the same warning? ... Luis - I mean the former... When I drag them into the trash I get a message that stops the process and says "Are you sure you want to delete ... More on discussions.apple.com
🌐 discussions.apple.com
🌐
Dropbox Help
help.dropbox.com › dropbox help center - how to use dropbox › delete and restore › "are you sure you want to delete this file" message
"Are you sure you want to delete this file" error message - Dropbox Help
You may see this pop-up message asking for your confirmation to delete a file or folder when you: Delete shared files or folders from your Dropbox folder on your computer. Move files or folders from a shared folder to a location that other members of the folder can't access (like a private folder or a folder not in your Dropbox account). Move files or folders out of your Dropbox folder. If you want to confirm the delete or move, click Delete or Move respectively.
🌐
Synology Community
community.synology.com › enu › forum › 1 › post › 190545
How to Disable the 'Are you sure you want to permanently ...
November 11, 2024 - Hi! Come and join us at Synology Community. A place to answer all your Synology questions. Ask a question or start a discussion now.
🌐
Windows 10 Forums
tenforums.com › general-support › 16392-disable-permanently-delete-files-confirmation.html
Disable Permanently Delete Files confirmation - Windows 10 Help Forums
Hello isolt, :) Only drives (ex: internal) that have a Recycle Bin that you can set these settings for. Removable media doesn't have a Recycle Bin for them, and will always permanently delete and ask for confirmation first. I'm not aware of any way around this yet.
Top answer
1 of 4
157

This is new behaviour, no?

Well, it's new behaviour since Windows 8.0.

I went through my collection of Mostly Legitimate Windows ISOs and installed all of them.

The option to enable/disable confirmations when sending files to Recycle Bin has been available ever since Windows 95 introduced the feature in general, but it was enabled by default up until Windows 7 (I tried SP1). However, fresh installations of Windows 8.0 and all later versions (8.1 all the way to 10.21H2) have the confirm prompt disabled by default.

Permanent deletion with Shift+Del or files too large for the Recycle Bin will still result in a confirmation dialog regardless of this setting. (Though oddly, if the entire Recycle Bin is manually turned off, prompts still remain disabled even though deletion is now permanent...)

Modern UI design seems to avoid confirm prompts for actions that are easily undone (e.g. restoring from Recycle Bin), so that when a confirmation dialog does show up, it actually means something important – and isn't as likely to get dismissed without even looking (alert fatigue).

For example, if the user gets prompted for all recycled files and habitually click "Yes", they're likely to never notice that sometimes the dialog says "File is too large for Recycle Bin, do you want to permanently delete it".

2 of 4
9

Windows Update is capable of changing settings without prior notice.

If this setting was changed, here are the places to look, where this confirmation could have been disabled.

  • Right-click the Recycle Bin, select Properties and verify that "Display delete confirmation dialog" is set.

  • Run gpedit.msc and navigate to
    User Configuration\Administrative Templates\Windows Components\File Explorer.
    Verify the setting of the policy named "Display confirmation dialog when deleting files".

  • Run regedit and navigate to the key
    HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\Policies\Explorer. Right-click the right pane, select New > DWORD (32-bit) Value and name this as ConfirmFileDelete. The value data should be 1 to enable.

Reference (and source of the images): How to Enable or Disable Delete Confirmation Dialog on Windows 10?

🌐
Digital Spy
forums.digitalspy.com › pc & mac hardware and software
Files not going to recycle bin - Windows 10 — Digital Spy
May 3, 2022 - If you deleted files by mistake ... you sure you want to permanently delete this file' is a warning that the file will be deleted without going into the recycle bin....
Find elsewhere
🌐
GitHub
github.com › microsoft › WSL › issues › 8796
Workaround for "Are you sure you want to permanently delete this folder/file?" · Issue #8796 · microsoft/WSL
September 4, 2022 - Is your feature request related to a problem? Please describe. When using explorer.exe to browse a WSL 2 file system and trying to delete a file you always get the "Are you sure you want to permanently delete this folder/file?" popup. A ...
🌐
Reddit
reddit.com › r/techsupport › win11 24h2, disable 'are you sure you want to permanently delete' dialog on network share?
r/techsupport on Reddit: win11 24h2, disable 'Are you sure you want to permanently delete' dialog on network share?
March 22, 2025 -

Hello, looking like this issue is impossible based on (google, microsoft search), but figured I'd ask here for a second eye, please -

Windows file explorer "Are you sure you want to permanently delete this [file / folder / shortcut]"[yes/no] is displayed when deleting files. This can be disabled by right click Recycle, properties, uncheck confirmation (to disable recycle confirmation) and disable the recycle bin entirely (to disable permanent confirmation). It can also be disabled by regedit hklm/hkcu ConfirmFileDelete:0, and gpedit 'Display confirmation dialog when deleting':disable.

I've done these and local files/folders delete without prompt (my desired behavior) whether delete or shift+del, however network drives(browsed via unc or drive letter mapped) continue to prompt - is there any way to disable the prompt on external/network drives?

(not looking for an alternative file browser, or command line methods, which would likely work and are what I'll use if windows native file explorer doesn't support this)

TIA

🌐
Digital Citizen
digitalcitizen.life › delete-files-temporarily-or-permanently-windows-10
How to delete files in Windows (permanently or temporarily)
October 11, 2025 - The permanent delete shortcut keys ... asked if you’re “[...] sure you want to permanently delete this item/these items?” press Yes....
🌐
Technipages
technipages.com › home › windows 11: disable “are you sure you want to move this file to the recycle bin?” dialog
Windows 11: Disable "Are you sure you want to move this file to the Recycle Bin?" Dialog
April 3, 2023 - Whenever you delete a file, Microsoft Windows 11 gives you a warning message that asks “Are you sure you want to move this file to the Recycle Bin?”. I’m very confident in what I choose to delete, so I don’t need to be warned about what ...
🌐
Apple Community
discussions.apple.com › thread › 254726847
How do I stop Finder from giving me a war… - Apple Community
"giving me a warning ("Are you sure you want to delete ...") ... Click on the Desktop and go to the Finder ➙ Settings menu option. Then · go to the Advanced section and make sure this checkbox is NOT CHECKED. One way to work around this (temporarly) is to give full permissions to evey user ...
🌐
MajorGeeks
majorgeeks.com › content › page › stop_windows_from_prompting_to_delete_a_file.html
Stop Windows From Prompting to Delete a File - MajorGeeks
December 23, 2020 - Name the new DWORD ConfirmFileDelete and confirm the Value data is 0 by double-clicking ConfirmFileDelete. If you'd like to delete a file without using the Recycle Bin, another trick is to hold the Shift key when deleting a file.
🌐
Dropbox Community
dropboxforum.com › the dropbox community › english › help › delete, edit, and organize
"Are you sure you want to delete this file" error message | The Dropbox Community
There is a way to re-enable a file system warning such as this, if you disabled it. Please try these steps. 1. Click on the Dropbox icon in your system tray/menu bar. 2. Click on your initials or profile pic 3. Click on preferences 4. In the Account tab, press 'Option/Alt key' (Mac) or 'Alt + H' (Windows). 5. Click on 'reset file system warning options' Let me know how it goes! ... Solve issues with deleting, editing, and organizing files and folders in your Dropbox account with support from the Dropbox Community.
🌐
Microsoft Community Hub
techcommunity.microsoft.com › microsoft community hub › communities › products › windows › windows insider program
How do I delete files permanently from my computer and make it unrecoverable? | Microsoft Community Hub
September 24, 2024 - Thank you very much for your help! ... Of course! I've totally been there, sweating over some old personal files. These days I swear by Dr-Wiper — it's a pro-level tool that uses some hardcore military-grade wiping to overwrite everything. Once it's done, that data is gone for good. No recovery, no worries. I followed this tutorial: https://www.anywinhub.com/permanently-delete-files-from-pc
🌐
Autodesk
autodesk.com › support › technical › article › caas › sfdcarticles › sfdcarticles › Are-you-sure-you-want-to-permanently-delete-this-file-when-running-CAMduct-in-Batch-Mode.html
"Are you sure you want to permanently delete this file" when running CAMduct in Batch Mode
October 8, 2023 - A prompt dialog appears in the background, and it is not responsive: Delete File Are you sure you want to permanently delete this file? This issue has been resolved in Fabrication CAMduct 2023 and later. Updates are available through Autodesk Desktop App or Autodesk Account
🌐
Eileen's Lounge
eileenslounge.com › viewtopic.php
"Are you sure you want to permanently delete this file?" - Eileen's Lounge
If it is the fact that you were asked to verify that yes you wanted to delete the file, then that is because there is a check mark in the setting pane is checked to ask.Hi Dave. It's not that I'm being "asked", but that I'm being "asked if I want to permanently delete" a file.
🌐
Computer Hope
computerhope.com › tips › tip48.htm
Delete Files Without Getting a Prompt
June 14, 2025 - How to delete files in Windows without a confirmation prompt. This guide provides tips for disabling the prompt temporarily or permanently for file management.
🌐
GitHub
github.com › microsoft › vscode › issues › 80309
The warning about deleting file under version control is too strong / unnecessary · Issue #80309 · microsoft/vscode
September 4, 2019 - When I'm about to delete a file that is version-controlled in my project, I get this warning: Are you sure you want to permanently delete 'some-file.txt'? This action is irreversible! I think it is too strong – in fact, it's technically ...
Author   borekb