How To Include Attachments When Replying In Outlook – Reply With Attachments Enabled

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Adding attachments when replying in Outlook is not automatic, but you can enable it with a quick setting change. If you have ever sent a reply and realized the original attachment was missing, you are not alone. This guide covers exactly how to include attachments when replying in Outlook for desktop, web, and mobile versions. You will learn built-in methods, workarounds, and best practices to save time and avoid confusion.

Why Attachments Disappear In Replies By Default

Outlook is designed to keep replies clean. When you reply to an email that includes a file, the program does not automatically carry that file forward. This prevents accidental sharing of sensitive documents or cluttering a conversation with large files. However, many users want the opposite behavior, especially in team projects or support tickets. Understanding this default helps you decide which method works best for your workflow.

Common Scenarios Where You Need Attachments In Replies

  • Responding to a client who sent a contract and needs your signed version
  • Following up on a support ticket where the original screenshot is essential
  • Sharing updated project files while keeping the original email thread intact
  • Forwarding a meeting request or calendar item that includes an attachment

How To Include Attachments When Replying In Outlook

This section walks you through the exact steps for different Outlook platforms. The process varies slightly depending on whether you use Outlook for Microsoft 365, Outlook 2019/2021, Outlook on the web, or the mobile app. Follow the method that matches your version.

Method 1: Manually Attach Files In A Reply

The simplest way is to attach the file yourself. This works in every version of Outlook and gives you full control over which files to include.

  1. Open the original email that contains the attachment.
  2. Click Reply or Reply All.
  3. In the new message window, go to the Insert tab.
  4. Click Attach File.
  5. Navigate to the file on your computer or select it from recent documents.
  6. Click Insert and then send your reply.

This method is reliable but takes extra steps. If you reply often with the same file, consider saving it to a folder for quick access.

Method 2: Drag And Drop The Attachment

Outlook supports drag and drop for attachments. This is faster than the menu method.

  1. Open the original email in a separate window (double-click it).
  2. Click and hold the attachment icon at the top of the email.
  3. Drag the attachment into the reply message body or the attachment area.
  4. Release the mouse button. The file appears as an attachment in your reply.

This works in Outlook desktop and Outlook on the web. On Mac, you may need to hold the Command key while dragging.

Method 3: Use The Forward Option Instead Of Reply

When you forward an email, Outlook automatically includes all original attachments. This is a quick workaround if you want the file to stay in the thread.

  1. Open the email with the attachment.
  2. Click Forward.
  3. Address the email to the same person who sent it (or to the group).
  4. Add your reply text at the top of the forwarded message.
  5. Send the email.

Be careful: forwarding shows the entire original message, which may include extra content you do not want to share. You can delete parts of the original email before sending.

Method 4: Enable The “Include Attachment When Replying” Add-In

Microsoft does not offer a built-in setting to automatically include attachments in replies. However, third-party add-ins can add this feature. One popular option is Reply With Attachment by VBOffice. It adds a button to your Outlook ribbon.

  1. Open Outlook and go to the Get Add-ins button (usually in the Home tab).
  2. Search for “Reply With Attachment” or “Include attachments in reply.”
  3. Select an add-in and click Add.
  4. Follow the installation prompts.
  5. After installation, a new button appears in the ribbon. Click it to reply with attachments automatically.

Add-ins may require a subscription or one-time payment. Check user reviews before installing.

Method 5: Use Quick Steps To Automate The Process

Outlook Quick Steps let you create custom one-click actions. You can build a Quick Step that replies with the original attachment attached.

  1. Go to the Home tab and click Quick Steps (in the ribbon).
  2. Select New Quick Step > Custom.
  3. Name it something like “Reply With Attachment.”
  4. Under Actions, choose Reply.
  5. Click Add Action and select Attach File.
  6. Choose the file you want to attach. This will attach the same file every time.
  7. Click Finish.

This method is best if you always reply with the same file (like a template or signature). It does not dynamically attach the file from the original email.

How To Include Attachments When Replying In Outlook On The Web

Outlook on the web (OWA) works slightly differently. The drag-and-drop method is the most efficient here.

Steps For Outlook Web App

  1. Log in to Outlook on the web (outlook.office.com).
  2. Open the email with the attachment.
  3. Click Reply or Reply All.
  4. In the reply pane, click the paperclip icon (Attach) in the toolbar.
  5. Select Browse this computer or Browse cloud locations.
  6. Choose the file and click Open.
  7. Send your reply.

You can also drag the attachment from the original email directly into the reply area. This works in most modern browsers.

How To Include Attachments When Replying In Outlook Mobile

The Outlook mobile app for iOS and Android has a simple interface. Attachments are not automatically included, but you can add them easily.

Steps For Outlook Mobile

  1. Open the Outlook app on your phone.
  2. Tap the email with the attachment.
  3. Tap the Reply icon (arrow pointing left).
  4. Tap the paperclip icon at the bottom of the screen.
  5. Select Attach File and choose from your phone storage, OneDrive, or other cloud services.
  6. Tap the send icon.

On Android, you may also long-press the attachment in the original email and select “Copy,” then paste it into the reply. This trick works inconsistently across devices.

Best Practices For Including Attachments In Replies

Follow these tips to avoid mistakes and keep your email professional.

  • Always double-check the attachment before sending. Make sure it is the correct file and version.
  • If the original file is large (over 10 MB), consider compressing it or sharing a link instead.
  • Use descriptive file names so the recipient knows what they are opening.
  • When replying to a group, think twice before including attachments. Not everyone may need the file.
  • If you use the forward method, remove any irrelevant parts of the original email to keep the thread clean.

Troubleshooting Common Issues

Sometimes attachments do not appear or cause errors. Here are fixes for frequent problems.

Attachment Not Showing In Reply

If you attached a file but it does not appear, try these steps:

  • Close and reopen the reply window.
  • Check if the file is still in its original location. If you moved or deleted it, Outlook cannot attach it.
  • Make sure the file is not too large. Outlook has a size limit (usually 20-25 MB for attachments).
  • Try attaching the file using a different method (drag and drop vs. menu).

Cannot Drag Attachment From Original Email

Drag and drop may fail if the original email is not in a separate window. Open the email by double-clicking it, then try again. Also, ensure you are not in reading pane mode.

Add-In Not Working

If a third-party add-in does not function, check for updates. Go to File > Office Account > Update Options. Also, disable and re-enable the add-in in File > Options > Add-ins.

Frequently Asked Questions

Can I Make Outlook Automatically Include Attachments In All Replies?

No built-in setting exists for this. You need a third-party add-in or use the forward method as a workaround. Some add-ins like “Reply With Attachment” add a button to automate the process.

Does Outlook For Mac Include Attachments When Replying?

Outlook for Mac behaves the same as the Windows version. Attachments are not included automatically. You can drag and drop or use the Attach File button in the ribbon.

Why Does My Attachment Disappear After I Send The Reply?

This usually happens if the file was deleted or moved after you attached it. Outlook links to the file location. If the file is no longer there, the attachment may fail. Always attach files from a stable location.

Can I Include Multiple Attachments In A Reply?

Yes, you can attach multiple files. Hold the Ctrl key (Windows) or Command key (Mac) while selecting files in the Attach File dialog. Or drag multiple files into the reply window.

Is There A Way To Include Attachments In Replies Without Downloading Them First?

If the attachment is stored in OneDrive or SharePoint, you can share a link instead of attaching the file. Click the paperclip icon, select Attach as copy or Attach as link. Links do not require downloading.

Summary Of Methods

Here is a quick reference table for the methods discussed.

Method Platform Effort
Manual attach via menu All versions Medium
Drag and drop Desktop, Web Low
Forward instead of reply All versions Low
Third-party add-in Desktop only Low after setup
Quick Steps Desktop only Medium after setup

Choose the method that fits your daily routine. For most users, drag and drop or the forward trick works best. If you handle many replies with attachments, consider investing in an add-in to save time.

Final Thoughts

Knowing how to include attachments when replying in Outlook saves you from resending emails or confusing your recipients. While the default behavior excludes attachments, the workarounds are simple once you learn them. Start with manual attachment or drag and drop. If you need automation, explore Quick Steps or add-ins. Test each method on a test email first to avoid mistakes. With these techniques, you can reply confidently and keep your attachments where they belong.