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

Question

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

Alex Fogerty 71

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.

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Any ideas how I can make this permanent?

ChristyZhang-MSFT 26,126 Reputation points Microsoft External Staff

2023-08-21T07:00:52.04+00:00

Hi @Alex Fogerty ,

Just checking in to see if above information was helpful. If it is useful, would you mind marking the helpful post as an answer? Which would benefit others who also has similar issues in forum.

4 answers

Your answer

ChristyZhang-MSFT 26,126 Reputation points Microsoft External Staff

2023-08-21T07:00:52.04+00:00

Hi @Alex Fogerty ,

Just checking in to see if above information was helpful. If it is useful, would you mind marking the helpful post as an answer? Which would benefit others who also has similar issues in forum.

Answer 1

Scott Royle 5

I don't really want to change the registry. Shouldn't there be an option for this? It has always come back in the past. I see Outlook got updated, maybe they fixed it. We will see if it comes back again.

Answer 2

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?

Lonnie Best 5 Reputation points

2025-06-17T07:01:58.32+00:00

I wish someone would answer robolovsky. I have the same problem. Users would like to uncheck that disabled checkbox: "Always ask before opening this type of file" to not be prompt each and every time they try to open a PDF from Outlook, but the box is checked and modification is disabled!

If a PDF contains code, that's when a big warning should appear! Most PDFs are safe. If a PDF is trying to do something fancy, that's what needs to be detected and warned about. This practice of make the user endure a warning on every single PDF is just ridiculous. Whoever made this decision, I'd like to put tape over their mouse's sensor. They deserve that.

Answer 3

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.)

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(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.)

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Scott Royle 5 Reputation points

2024-06-03T14:40:04.0133333+00:00

I don't want to change the registry. It has always come back in the past. Shouldn't there be a normal option for this? Maybe the new update changed this, we will see.

Answer 4

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.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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

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