Outlook gives warning message about opening PDFs, but after unticking Always Ask the message comes back

Question

Hi guys,

An end user is seeing this warning message when they go to open a PDF attachment. If I close Outlook and open Outlook as an administrator I can then untick the "Always ask before opening this type of file" and then close and open Outlook again and the prompt is gone.

The problem is that up to a week later the warning message comes back. I don't know why this is, but given the timing I assume it is Microsoft Office Updates. I have run a repair on Office, both Quick and Full, but the warning message continues to come back. I assume that a registry key is being overwritten.

This seems to have started after the client went to Microsoft 365. This might seem like a trivial thing but the end user processes hundreds of PDF invoices a day and this is killing their productivity.

Any ideas how I can make this permanent?

Answer 1

I have the exact same problem in Outlook 2021 and can only imagine that this is a general issue with Outlook. The warning message appears before certain attachments such as PDF files can be opened. There is specifically a tick box to disable the warning but this is grayed out. If I close Outlook and open Outlook as an administrator I can then untick the "Always ask before opening this type of file" box and the prompt no longer appears. Unfortunately this is not permanent and after a week or so the prompt returns and as before, the option to untick the "Always ask..." box is grayed out. Like others, I suspect that it is an update which resets the prompt.

What I would like to know is, why is the option to disable this warning, grayed out in the first place. What is the point in having the option if the only way you can use it is to run the program as Administrator. I am the admin of my own computer so why do I specifically have to do this. It doesn't make any sense to me.

At the very least if we do go to the trouble of unticking the box, it should stay like that and not keep coming back. Can Microsoft release an update to fix this behaviour please?

Answer 2

Hi @Alex Fogerty ,

Welcome to our forum!

Does this issue occur recently? If so, have you done any specific operations before that?

Considering that you have tried to disable it manually, it's suggested that you could try to disable it by registry. More information: Disable "Always ask before opening" Dialog.

(Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)

(Note: Serious problems can occur if you modify the registry incorrectly. Before making changes, back up the registry to restore it in case something goes wrong.)

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Answer 3

Hi @Alex Fogerty ,

Microsoft Office updates may have overwritten a registry key, resulting in the recurrent warning notice for PDF attachments in Outlook. Consider configuring the registry key with the desired value and then implementing a Group Policy Object (GPO) or script to enforce this configuration, making it permanent for the user, to address this issue.

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Answer 4

Hi Iftikhar Ali

You are quite correct. The Registry key that I created as per the previous post in this thread had been removed by some process that I am unaware of, hence the prompt to Open/Save an attached PDF returned a few days later.

Your suggestion of implementing a GPO or script to enforce this configuration making it permanent is what I would like to do, but I don't know if this can be done on my single user Windows 10 PC that is not on a network.

If it can be done, I would be grateful for some instructions.

Answer 5

Its almost 2026 and I have a user at our company experiencing the same issue. From my research, even the registry entries will be overwritten