For me, it was the same problem, it didn't ask me if I'm sure. But I unchecked the checkbox in settings and clicked OK, then opened settings and checked it again and now it is working.

@Vit Hauptman: Thanks for your suggestion.
We will see, if more people ask for this.

Hello,
please is it possible to change default selected button?
Just now is by default selected YES so that, when by mistake is pressed DEL and ENTER the file is deleted :-(

Martin, sent you an email with some screenshot attachments to illustrate.
Look forward to hearing. Thx

Can you send me an email, so I can send you back a debug version of WinSCP to track the problem? Please include link back to this topic in your email. Also note in this topic that you have sent the email. Thanks.

Martin, actually, the screenshot did include the (Environment/Confirmations) settings and you're right, I failed to select the Moving files to Recycle bin box there. However, Local >> Delete files to Recycle bin was checked off as the screenshot shows.

The problem is that, although that option was checked, it didn't move deleted local files to the local recycle bin. I now did check the Confirmations >> Moving files to Recycle bin box but unfortunately, even though I am now asked to confirm the delete to the Recycle bin, the deleted (local) file still does not show up in my notebook's recycle bin so it seems like I am still no further ahead.

The question therefore stands, what other setting(s) have to be changed to delete local files to my local recycle bin.

BTW, the delete confirmation box for Windows 10 is activated

Looking forward to a solution to this. Thanks

OK, you are not using WinSCP "Delete" command in 5.1.2. You are using system "Delete" command from system context menu. The delete confirmation is Windows Explorer confirmation. For this confirmation, the Windows Explorer setting applies (which is off by default in recent version of Windows, btw), not WinSCP settings.

In 5.7.6, WinSCP uses its own context menu for local files, instead of the system context menu. So you use WinSCP "Delete" command in 5.7.6. For this, the WinSCP setting (Confirmations) Moving files to Recycle bin applies. That confirmation is on by default. You must have turned it off. But you didn't show us the screenshot for this.

Attached are screen prints from both versions. 5.1.2 had the delete confirmation box included that does not show up with the settings shown for 5.7.6

So can you help me resolving this?

In you current 5.1.2, what is the state of (Confirmations) Moving files to Recycle bin and Delete local files to recycle bin? Can you attach a screenshot of the confirmation window and the preferences?

If you upgrade to 5.7.6, what is the state of the same options? Screenshots?

Martin, in that case something does not work as you indicate. NONE of edited html files I have worked on and deleted since upgrading to the latest version are in the recycle bin. They appear to be lost forever. This makes me extremely nervous. Next time I highlight a file for deletion by mistake it will be gone for good.

Just to confirm, I logged on remotely to my main development PC where I am running version 5.1.2 (build 2816) and it does ask confirmation of removal on the local directory as well. It is very unfortunate that this confirmation is not offered for local files in the latest version I am running on my laptop 5.7.6 (build 5874), especially after just having made a donation!

Will have no choice but to roll back to 5.1.2 until this major issue is fixed. Very disappointed.

The confirmation of deleting file is on by default.

On local panel, the files a not deleted by default, but moved to recycle bin:
https://winscp.net/eng/docs/ui_pref_panels_local

So the Moving files to Recycle bin option applies. Which is on too by default anyway.

Actually deleting remote files will get the dialog box, just not the local files.

I recently upgraded to version 5.5.5 (Build 4605) and found that, even though the checkbox in preferences to confirm deleting files is on, the file deletes without a confirmation dialog.
Also noticed that, after clean install, this option is NOT checked by default, although it states that use of this option is "recommended".
Love to hear how to get the confirmation dialog back.
Thanks