Outlook 2019 Reply All Does Not Include Original Attachments

Quick Answer

In Outlook 2019, attachments from the original email are not automatically included when you select Reply or Reply All. This is normal Outlook behavior, not necessarily an error with your Outlook installation.

Microsoft's Outlook documentation confirms that attachments are not included when replying to a message. If you need to send the original attachments with your reply, you must manually add them to the reply. [Microsoft Support – Reply to or forward an email message](https://support.microsoft.com/en-us/outlook/reply-to-or-forward-an-email-message?utm_source=chatgpt.com)

Why Are the Attachments Missing When Using Reply All?

Reply All creates a new reply addressed to the original sender and the other recipients on the original message's To and Cc lines. However, Outlook does not automatically copy the original message's attachments into the reply.

This behavior is intentional. Automatically returning the same files to the sender would often be unnecessary because the sender already has the original attachments.

Microsoft documents the same behavior for Outlook 2019: attachments are not included when replying, while attachments from the original message are automatically included when the message is forwarded. [Microsoft Support – Reply to or forward an email message](https://support.microsoft.com/en-us/outlook/reply-to-or-forward-an-email-message?utm_source=chatgpt.com)

How to Reply All With the Original Attachments

If you need to keep Reply All and also send the files that were attached to the original email, manually add the attachments to your reply.

Method 1: Copy the Attachments and Paste Them Into Reply All

1. Open the original email in your Inbox.
2. Locate the attachments displayed with the message.
3. Select the attachment or attachments you want to send again.
4. Copy the selected attachments using Ctrl+C.
5. Click Reply All.
6. If the reply opens in the Reading Pane, select Pop Out to open the reply in a separate window.
7. Click inside the reply message window and press Ctrl+V.
8. Confirm that the attachment names appear in the reply.
9. Write your response and select Send.

If selecting the attachments with Ctrl+A also selects other content, select the required attachments individually instead of using Ctrl+A.

Method 2: Save the Attachments and Reattach Them

If copying and pasting the attachments does not work reliably, save the original attachments to your computer and then attach them to the reply.

1. Open the original email.
2. Right-click the required attachment and select Save As.
3. Save the file to a known folder on your computer.
4. Click Reply All.
5. In the reply window, select Message > Attach File.
6. Browse to the folder where you saved the attachment.
7. Select the file and attach it to the reply.
8. Repeat the process for additional attachments.
9. Verify that all required files are attached before sending the email.

Microsoft's documentation for classic Outlook confirms that files can be added to an existing Reply or Reply All message using the attachment command. [Microsoft Support – Add pictures or attach files to emails in Outlook](https://support.microsoft.com/en-us/outlook/mail/add-pictures-or-attach-files-to-emails-in-outlook?utm_source=chatgpt.com)

How to Keep Reply All Recipients

If it is important that everyone who received the original message receives your response, use Reply All rather than Reply.

Before sending, check the To and Cc fields to confirm that the required recipients are still present. Outlook allows recipients to be added or removed from a reply before sending. [Microsoft Support – Reply to or forward an email message](https://support.microsoft.com/en-us/outlook/reply-to-or-forward-an-email-message?utm_source=chatgpt.com)

Alternative: Use Forward

If your intention is simply to send the original email and all its original attachments to other recipients, Forward may be more appropriate than Reply All.

Unlike Reply All, Outlook automatically includes the attachments from the original message when you forward it. [Microsoft Support – Reply to or forward an email message](https://support.microsoft.com/en-us/outlook/reply-to-or-forward-an-email-message?utm_source=chatgpt.com)

However, Forward changes the purpose of the message and the recipient list. If you need to respond to everyone already included in the original email, use Reply All and manually attach the required files.

Reply All vs. Forward

How to Verify the Attachments Before Sending

Before selecting Send, check the attachment area of the reply window.

• Confirm that every required file is displayed.
• Check the file names.
• Check that the correct versions of the files are attached.
• Make sure the files are not accidentally omitted after editing the message.
• Confirm that the intended recipients are present in the To and Cc fields.

Do not assume that an attachment was included simply because the original email contained it. Outlook does not automatically carry original attachments into a Reply or Reply All message.

Important: Attachment Security

Be careful when opening or re-sending email attachments. Microsoft notes that attachments are a common method of spreading computer viruses and that Outlook blocks certain potentially unsafe file types. [Microsoft Support – Blocked attachments in Outlook](https://support.microsoft.com/en-us/outlook/blocked-attachments-in-outlook?utm_source=chatgpt.com)

Frequently Asked Questions

Is it normal that Outlook 2019 does not show attachments after clicking Reply All?

Yes. Outlook 2019 does not automatically include the attachments from the original message when you use Reply or Reply All.

Can I use Reply All and still send the original attachments?

Yes. Use Reply All and manually add the required attachments to the reply.

Why does Forward include the attachments but Reply All does not?

Outlook treats Forward as a new message intended for other recipients and automatically includes the original attachments. Reply and Reply All are treated as responses, so the original attachments are not automatically included.

Can I copy the attachment from the original email and paste it into the Reply All message?

Yes, you can try copying the attachment from the original message and pasting it into the reply window. If this does not work, save the attachment and use the Attach File option in the reply.

Do I need to download the attachment before replying?

Not necessarily. If copying and pasting the attachment works in your Outlook installation, you can add it directly to the reply. Otherwise, save the attachment locally and attach it again.

Will Reply All automatically include recipients from the original email?

Reply All sends the response to the original sender and the other recipients on the original message's To and Cc lines. Always review the recipient fields before sending.

Should I use Forward instead of Reply All?

Use Reply All when you need to respond to the existing recipients. Use Forward when you need to send the original message and its attachments to other recipients.

Conclusion

The missing attachments when using Reply All in Outlook 2019 are generally expected behavior. Outlook does not automatically include attachments from the original message in a reply.

If the original files must be included, use Reply All and manually copy/paste the attachments or save and reattach them. If you need to send the original message with its attachments to different recipients, use Forward instead.

Sources

• [Microsoft Support – Reply to or forward an email message](https://support.microsoft.com/en-us/outlook/reply-to-or-forward-an-email-message?utm_source=chatgpt.com)
• [Microsoft Support – Add pictures or attach files to emails in Outlook](https://support.microsoft.com/en-us/outlook/mail/add-pictures-or-attach-files-to-emails-in-outlook?utm_source=chatgpt.com)
• [Microsoft Support – Blocked attachments in Outlook](https://support.microsoft.com/en-us/outlook/blocked-attachments-in-outlook?utm_source=chatgpt.com)