How to Keep Attachments When Replying in Outlook

Going through an email thread with a client or colleague can be quite frustrating when attachments that were originally included do not appear. Using valuable time to locate the original message with the required attachment may appear to be a waste of time. When forwarding an email, Microsoft Outlook saves attachments, but not when replying. You’ll learn how to keep attachments when replying to an email in Outlook in this article.

1)    Manually copy & paste attachments into the replying message 


When replying to an email, attachments may not automatically be included. However, you have the option to simply copy and paste them into the forwarding mail.


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Step 1: Click on the email you’d like to reply to and right-click on an attachment you’d like to send with your reply.

Step 2: Click “Select All” from the drop-down menu.


Step 3: Copy the attachments with the corresponding key combination or right-click again and choose “Copy” from the drop-down menu.


Step 4: Select the “Reply” button on the “Home” tab or toolbar.


Step 5: Click on the “Paste” button on the “Message” tab. Your attachments will now be kept in your replying message.

2)    Drag & Drop  

Step 1: To open it in an extra window, double-click the message you’d like to reply to and select “Reply” on the Home tab.


Step 2: Minimize the reply message and the original one so that both are shown on the same screen.


Step 3: Select all attachments you’d like to be in your replying message. Then simply drag and drop them in the replying message.

3)    Forward emails instead 

Another easy strategy to reply to an email with attachments is to select the “Forward” instead of the “Reply” option. When forwarding an email, Outlook keeps the attachments automatically. Simply adding the email address of the sender will have the same outcome as using the reply function, but attachments will be included.


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4)    Download Outlook add-in

If the presented workaround strategies are still too much effort to keep attachments when replying to an email, you may want to download an external add-in like ReplyWithAtt by IvaSoft. This add-in integrates with Outlook’s default Reply and Reply All and includes all the attachments when replying without the need to configure anything.

5)    Auto add via VBA macro

You may also want to consider using the VBA macro which will help you reply with the original attachments included. Learn here how to do so.

Note that you’ll have to enable macros in your Microsoft Outlook. To do so, learn here how to disable and enable macros in Outlook.

What is your favorite strategy to keep attachments when replying to a message? Let’s have a discussion in the comment section! 

See you seen!

Aline & the Lookeen team

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