Opening Attachments in Oultook (Classic) mail items

I have an issue in opening attachments in Outlook (Classic)




I guess it's something in the 'Trust Centre' that is causing this; however, after trying several combinations of settings I can't seem to find the right one.

What I would like to do is when I double-click on an attachment I would like it to open up without going via the pop-up.

Can any one advise what I shoould do?

IanMosley said:

Can any one advise what I shoould do?

Click to expand...

I was going to, but, I see you don't have the ability to uncheck the Always ask before... box!

Courtesy of co-pilot
My question -how to stop attachments in outlook classic from asking if I want to open or save file

You’re running into the “Do you want to open or save this file?” prompt that appears every time you open an attachment in Outlook Classic. That dialog doesn’t come from Outlook itself — it comes from Windows Attachment Manager, and you can disable it per file type.

Below is the clean, reliable way to stop it.

​

​

Windows hides the old “Always ask” checkbox, so you clear the security flag manually.

Steps​

1. Save one attachment of that file type to your computer
2. Right‑click the saved file → Properties
3. At the bottom, look for “Unblock”
4. Check Unblock → Apply

Once you unblock a file of that type, Outlook stops asking for that extension (PDF, DOCX, XLSX, JPG, etc.).

​

Some systems still expose the classic UI.

Steps​

1. Press Win + R
2. Type:
   
   
   
   control folders<br>
3. Go to File Types tab
4. Find the extension (e.g., PDF, DOCX)
5. Click Advanced
6. Uncheck:“Always ask before opening this file type”

​

If the Unblock button is missing, you can remove the security flag directly.

Steps​

1. Open Registry Editor
2. Go to:
   
   Code
   
   HKEY_CURRENT_USER\Software\Microsoft\Windows\Shell\AttachmentExecute<br>
3. Inside, you’ll see subkeys like:
   
   • {0002DF01-0000-0000-C000-000000000046} (IE/Edge)
   • {FFB8655F-81B9-4FCE-B89C-9A6C7D43A315} (Explorer)
4. Under the correct subkey, delete the entry for the file extensionExample:
   
   • Delete .pdf
   • Delete .docx

This removes the “always ask” flag for that file type.

Hi Ian,

Your email address is exposed in your screenshot. I suggest you block it out.

Kind regards,

tecknot

Do not see any problem, attachments are a security risk, it's worth keeping the reminder.
I have an additional warning Red flag for Emails with attachments.

Also it is wise not to expose your Email address in posts as that will result in it being farmed and then spammed.