Change app to open email attachment

Question

At my company we send files to clients via email. These pdf documents contain maybe 8 pages but the clint only gets 3 of them, so we have to delete some before we send.

This is a feature we have long been able to accomplish by attaching the PDF to the email, right clicking the attachment and opening it using Adobe Acrobat Pro, then deleting the pages that the client does not get. When we edit and save the pdf this way, it does not change the original file in our client files, it only changes the attachment, which is ideal.

We recently updated to the newest version of outlook (previously using 2013) and also updated from physical server holding all of our client files to the cloud. Now there is no option to open with a different app in outlook when we right click, and we can not get the attachments to open in Adobe Acrobat Pro despite monkeying with as many attachment settings as we can find. I have not been able to find the answer to this issue in other threads because this is about opening attachments BEFORE you send the email, not about how they open when you double click an attachment you received or sent already.

TLDR: How do I change the settings in outlook to open my pre-sent attachments in a different program?

Answer 1

Hello Lynn Born, Good day!Thank you for posting to the Microsoft Community. We are happy to help you.Based on the description you have shared; we understand that you have trouble opening attachments in Outlook before you send them. We are sorry to hear that you have trouble with your outlook.

-It's important to know the type of account and Outlook version you're using because each account and Outlook version has a different process and a different support category.

Note: If you have a Microsoft 365 subscription or non-subscription version such as Office Home and Business  2013, in most cases you can't run these versions together on the same computer.

However, to better understand the problem and provide a solution, we need more details from you, please provide us with the following information. Thank you.

1-What type of account is affected? is Outlook.com account, Hotmail account, or professional/educational account example: ******@companydomain.com

2-Are you using a non-subscription version such as 2013 Home and Business or Office 365 subscription?

3- Can you share a screenshot of your Outlook version as in the picture below? What version of Outlook do I have? - Microsoft Support

4-Please, can I know the type of the affected account? Is it an IMAP, POP, or exchange account?   

5- In the latest version of Office 365 or business there is not option to open with another app

Since the option to open attachments with a different app is no longer available in the right-click menu, we can try a workaround using the "Save As" feature in Outlook. Here's what you can do:

1. Start by composing a new email and attaching the PDF file you want to edit.
2. Instead of sending the email, click on the drop-down arrow next to the attachment and select "Save As" to save the attachment to your computer.
3. Browse to the location where you saved the attachment and find the PDF file.
4. Right-click on the PDF file and select "Open With" from the context menu. Choose "Adobe Acrobat Pro" from the options provided.
5. Now you can edit the PDF in Adobe Acrobat Pro, deleting the unnecessary pages as required.
6. After you have made the necessary edits, save the changes using the "Save" or "Save As" option within Adobe Acrobat Pro.
7. Finally, go back to your draft email in Outlook, delete the old attachment, and attach the updated version of the PDF file that you saved.

By following these steps, you should be able to open the attachment in Adobe Acrobat Pro, make the required edits, and attach the updated version to the email.

We look forward to your reply. This requested information will help us narrow down the scenario and find the right troubleshooting. We will continue to assist you based on the information you provide. I sincerely appreciate your patience and cooperation. Sincerely,Eben Ezer Tres | Microsoft Community Moderator

Answer 2

company domain with office 365 subscription