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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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".
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.mscand navigate to
User Configuration\Administrative Templates\Windows Components\File Explorer.
Verify the setting of the policy named "Display confirmation dialog when deleting files".
Run
regeditand 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 asConfirmFileDelete. The value data should be1to enable.
Reference (and source of the images): How to Enable or Disable Delete Confirmation Dialog on Windows 10?
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
MIcrosoft Support KB 320031,
HOW TO: Bypass the Recycle Bin When You Delete Files and Folders in Windows XP
Permanently Bypass the Recycle Bin
You can permanently bypass the Recycle Bin by changing the configuration of the Recycle Bin:
- Right-click the Recycle Bin, and then click Properties.
- In the Recycle Bin Properties dialog box,
click to select the Do not move files to the Recycle Bin.- Remove files immediately when deleted check box.
- Click OK.
You can also configure Windows XP to skip the confirmation message whether or not you are using the Recycle Bin. In the Recycle Bin Properties dialog box, click to clear the Display delete confirmation dialog check box, and then click OK.
ps: I moved away from XP some time back; can't confirm this. Note that a permanent bypass might be dangerous.
Tell me if it works for you.
Follow these steps:
- Right click on the Recycle Bin and select
properties. - Uncheck the
Display delete confirmaion dialog box. - Click
Applythen OK.