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
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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?

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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....
Discussions

Annoying warning: "Are you sure you want to permanently delete this file?"
When deleting files stored on my Windows PC drives, I don't get any warning message when deleting files since I deactivated that in the recycle bin options. 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... More on truenas.com
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September 11, 2016
How do I delete files permanently from my computer and make it unrecoverable?
Hi everyone, I was organizing my computer recently and found some old files and sensitive data that I want to completely delete. I don't want these files to... More on techcommunity.microsoft.com
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September 24, 2024
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
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Files are permanently deleted, even if dragged to the recycle bin
Hi, where are the files located? If deleting files from USB or a network location then they don't go to the recycle bin. More on reddit.com
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February 17, 2022
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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.
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Digital Citizen
digitalcitizen.life › delete-files-temporarily-or-permanently-windows-10
How to delete files in Windows (permanently or temporarily)
October 11, 2025 - When asked if you’re “[...] sure you want to permanently delete this item/these items?” press Yes. Are you sure you want to permanently delete these items? Every selected file is gone from your Windows 10 or Windows 11 PC without being ...
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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".

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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?

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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 - I do know that it's there to remind you that the files don't end up in the recycle bin when deleted from network shares (though they can be protected by ZFS snapshots, so the message is probably reasonably safe to deactivate). You'll probably have better luck in a Windows-centric forum.
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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 - Hi everyone, I was organizing my computer recently and found some old files and sensitive data that I want to completely delete. I don't want these files to be restored, and I feel that ordinary deletion methods, such as right-clicking to delete or emptying the Recycle Bin, may still leave traces of data.
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AVG
avg.com › en › signal › delete-files-windows
Windows: How to Permanently and Securely Delete Files
December 10, 2025 - Here’s how to permanently delete files on Windows 10. Select the file you want to permanently delete and press Shift + Delete together. Windows will ask you to confirm. Click Yes.
Find elsewhere
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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 - Windows will protect you from accidentally deleting a file by prompting you before you delete a file to the Recycle Bin. Here's how you can easily disable the prompt before deleting a file. For example, Windows will show you a prompt that asks, "Are you sure you want to move this file to the Recycle Bin?"
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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 ...
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Computer Hope
computerhope.com › tips › tip48.htm
Delete Files Without Getting a Prompt
June 14, 2025 - Delete files faster by removing the "Are you sure you want to delete" Microsoft Windows confirmation box for all files by right-clicking the Recycle Bin icon on the desktop. In the pop-up menu, click Properties and uncheck Display delete ...
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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

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Reddit
reddit.com › r/windowshelp › files are permanently deleted, even if dragged to the recycle bin
r/WindowsHelp on Reddit: Files are permanently deleted, even if dragged to the recycle bin
February 17, 2022 -

Strange problem:

Whenever I delete a file on my Windows 10 -laptop, the pop-up window asks "Are you sure you want this file to be permanently deleted" (or something along those line, my system language is finnish).

However, the settings in my recycle bin are set so that the files should first go there, and be permanently deleted upon emptying the bin.

Even if I drag a file to the bin, the same window appears, saying "Are you sure you want this file to be permanently deleted".

What could be the problem? Thanks in advance!

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Reddit
reddit.com › r/synology › windows mapped drive - disable delete confirmation
r/synology on Reddit: Windows Mapped Drive - Disable Delete Confirmation
March 26, 2024 -

I have a Synology NAS with a Windows mapped drive that is configured to reconnect at logon. Any time that I attempted to delete a file from this mapped drive within Windows File Explorer, I was presented with a dialog box that asked "are you sure you want to permanently delete" the file.

My desired action is that the file be completely deleted and not moved to the Recycle Bin.

Most answers that I found on the internet incorrectly identified the solution as something that uses Group Policy, a registry change, or the additional step of using SHIFT+DELETE (which may work, but was not an answer to the problem). Some answers suggested modifying the properties of the Recycle Bin, and choosing "Don't move files to the Recycle Bin". This was not a solution for a mapped drive because a mapped drive did not appear in the list of Recycle Bin Locations; only my local drives (and Google Drives) showed up there.

I found the solution on an archived forum from several years back; the usernames were no longer with the post so I cannot thank OP for the solution that they provided.

To make a mapped drive show up in the list of Recycle Bin Locations so that you can configure it's behavior in the Recycle Bin properties, you can move one of the folders from your user profile to the mapped drive; this will make the mapped drive then show up in Recycle Bin Locations.

Under C:\Users\[yourUser]\, move one of these folders by right-clicking the folder, choosing properties, and then choosing the "Location" tab. Click "Move" and browse to the root of your mapped drive, and click "Select Folder."

I chose to move the "Searches" folder; I've never known anyone to use it. If you do use it, I would love to know how you utilize it.

Open the properties of the "Recycle Bin" and untick the "Display delete confirmation dialog" option for the mapped drive.

I hope that this helps someone get to a similar solution faster than I was able to!

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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 I’m deleting.
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Avast
avast.com › c-permanently-delete-files
How to Permanently Delete Files on PC | Windows 10 & 11
December 16, 2024 - If you’re looking to keep certain ... that people can use to steal your identity, then you need to make sure these files are permanently deleted and wiped from your drive....
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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.
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Super User
superuser.com › questions › 1357437 › windows-10-disable-the-permanently-delete-file-option
Windows 10: Disable the permanently delete file option - Super User
September 12, 2018 - Unfortunately I was addicted to permanently deleting files using the "Shift" key. And obviously I regret it from time to time. Is there a way to disable this option - meaning to be able to ONLY s...