Missing Attachments in Outlook

Question

Whenever I reply to or forward an email the attachments that were shared with me get stripped out. Then the person whom I've sent the email to ends up asking me for the attachment. This is a real waste of time. How do I fix this. The "new" outlook seems much less intuitive than classic.

Answer 1

Hi @Marilyn R Kaufman, 

Good day and welcome to Microsoft Q&A. 

I appreciate you bringing this to our attention, and I understand how important it is to ensure attachments are consistently included when replying to or forwarding emails, especially in the new Outlook experience. This behavior is unfortunately common in the New Outlook experience, but there are a few things we can try to fix it. 

To help streamline your workflow and avoid any confusion for recipients, here are a few options you can use to make sure attachments are preserved: 

Please note: All screenshots below reflect the steps in the New Outlook desktop app to ensure clarity when following along.

Option 1: Use “Forward as Attachment” 

If you’d like to retain the original file, the best approach is to use Forward as attachment, which sends the entire message—including attachments—as a file. 

1. Open the message.  
2. Select the More actions (…) menu in the message toolbar > Other reply actions.  
3. Choose Forward as attachment.  

   This will send the original message as an attachment, preserving the files it contains.  

Option 2: When attachments appear as links  

If the sender attached a file from OneDrive or SharePoint, Outlook may share it as a link by default. If you want to send the actual file:   

1. Right-click the attachment.  
2. Select Attach as a copy.     

This ensures the recipient receives the file itself, not just a link.  

Option 3: Viewing messages in conversation view  

To help you keep track of attachments across replies and forwards, you can enable conversation view:   

1. Select View from the top menu.  
2. Choose Messages > Conversations > Message list > Group messages by conversation.  
3. Pick whether to apply the setting to the current folder or all folders.  

With this enabled, related messages are grouped together, making it easier to track attachments and context.  

Option 4: Switching back to Classic Outlook   

If you prefer the behavior in the classic Outlook, you can easily switch back:  

1. In the upper-right corner of the Outlook window, turn off the New Outlook toggle.  
2. This will reopen your mailbox in the classic Outlook app with the attachment handling you are used to.  

To better understand what’s happening, could you let me know: 

• If this happens with all attachments or just specific ones 
• Whether you’re replying from the inbox, conversation view, or search results 

Once I have a bit more detail, I’ll be happy to guide you through the best solution. 

Note: We appreciate your understanding regarding the scope of support available through this forum. As moderators, our role is to provide general guidance and assist with common troubleshooting steps. While we do not have access to internal systems or administrative tools required to resolve account-specific or backend-related issues but we’ll continue doing our best to support you within the scope of our responsibilities.     

I hope the information provided proves useful. Please proceed with the outlined steps and let me know whether they resolve the issue. If not, I’ll be glad to continue working with you to find a solution. 

Thank you for your patience and understanding throughout this process. Should you have any questions or need further assistance, feel free to reach out at any time. 

 

I look forward to hearing from you. 

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