How To Include Original Attachments When Replying In Outlook – Original Files Preservation Technique

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Keeping original attachments when replying in Outlook prevents your recipients from losing important files you received. Learning how to include original attachments when replying in Outlook is a simple but powerful skill that saves time and avoids confusion. Many users accidentally remove attachments when they hit Reply, forcing them to reattach files manually. This guide walks you through every method, from default settings to advanced tricks, so you never lose a file again.

Outlook handles attachments differently depending on whether you Reply, Reply All, or Forward. By default, replying removes attachments, while forwarding keeps them. This behavior catches people off guard, especially when they need to share original documents without extra steps.

Let’s fix that right now. You’ll learn the exact steps for Outlook desktop, web, and mobile apps. We’ll also cover workarounds for stubborn versions and common troubleshooting tips.

How To Include Original Attachments When Replying In Outlook

This section covers the core methods. Each approach works for specific Outlook versions, so pick the one that matches your setup.

Method 1: Use The Forward Button Instead Of Reply

The simplest trick is to use Forward instead of Reply. Forwarding always keeps attachments intact. Here’s how:

  1. Open the email with attachments you want to keep.
  2. Click the Forward button (not Reply or Reply All).
  3. In the To field, type the original sender’s email address.
  4. Add your reply text above the forwarded message.
  5. Hit Send.

This method works in all Outlook versions. The downside is you must manually enter the recipient’s address. For frequent contacts, save their email in your address book to speed things up.

Method 2: Enable The “Include Attachments When Replying” Add-In

Microsoft offers a free add-in called “Include Attachments when Replying” for Outlook desktop. It adds a toggle button to your ribbon. Follow these steps:

  1. Go to File > Options > Add-ins in Outlook.
  2. At the bottom, set Manage to “COM Add-ins” and click Go.
  3. Check “Include Attachments when Replying” if it’s listed. If not, download it from Microsoft’s official site.
  4. Restart Outlook. You’ll see a new button in the ribbon when composing a reply.
  5. Click that button to toggle attachment inclusion on or off.

This add-in is reliable for Office 365 and Outlook 2016/2019. Some users report it missing in newer builds, so check your version first.

Method 3: Manually Drag Attachments From The Original Email

If you prefer not to install add-ins, drag and drop works perfectly. Here’s the step-by-step:

  1. Open the original email with attachments.
  2. Click Reply or Reply All as usual.
  3. In the reply window, minimize it so you can see the original email behind it.
  4. Click and hold the attachment icon in the original email.
  5. Drag it into the reply window’s attachment area (the paperclip icon or the message body).
  6. Release the mouse button. The attachment appears in your reply.

This method works in Outlook desktop and web. On Mac, you might need to use Cmd+Drag instead of just dragging.

Method 4: Use The “Attach Item” Feature

Outlook’s “Attach Item” feature lets you attach the original email as a file. This includes all attachments inside it. Here’s how:

  1. Start a reply to the email.
  2. In the reply window, go to the Insert tab.
  3. Click “Attach Item” (or “Outlook Item” in older versions).
  4. Select the original email from your inbox.
  5. Choose “Insert as Text” or “Insert as Attachment.” The latter keeps the original attachments bundled.
  6. Send your reply.

This method adds the entire email as an attachment. Recipients can open it to see the original files. It’s a bit clunky but works universally.

Outlook Web App (OWA) And Mobile Solutions

Web and mobile versions of Outlook behave differently. Let’s cover those separately.

How To Keep Attachments In Outlook Web

Outlook on the web (OWA) removes attachments when replying by default. Use these workarounds:

  • Forward trick: Click Forward, then change the recipient to the original sender.
  • Drag and drop: Open the original email in a separate window, then drag attachments into the reply.
  • Copy and paste: Right-click the attachment in the original email, select “Copy,” then paste into the reply window. This works for images and small files.

OWA doesn’t support add-ins, so manual methods are your only option. For frequent use, consider switching to the desktop app.

How To Keep Attachments In Outlook Mobile (IOS/Android)

The Outlook mobile app also strips attachments on reply. Here’s what you can do:

  • Forward method: Tap the forward icon, enter the sender’s email, and type your reply.
  • Share option: Open the attachment, tap the share icon, and send it via email again.
  • Save and reattach: Download the attachment to your phone, then attach it manually in the reply.

Mobile versions are limited. The forward method is the fastest. If you reply often, use a desktop or web version instead.

Advanced Tips And Customizations

These tricks help you automate or streamline the process.

Create A Quick Step For Attachments

Outlook’s Quick Steps let you automate repetitive tasks. Set one up to reply with attachments:

  1. Go to the Home tab in Outlook.
  2. Click Quick Steps > Create New.
  3. Name it “Reply with Attachments.”
  4. Choose an action like “Reply” and then “Attach Message.”
  5. Assign a shortcut key (e.g., Ctrl+Shift+1).
  6. Click Finish.

Now, when you press the shortcut, Outlook starts a reply with the original email attached. The recipient gets the full message including attachments.

Use VBA Macros For Advanced Users

If you’re comfortable with code, a VBA macro can force attachments to stay. Here’s a simple one:

Sub ReplyWithAttachments()
    Dim olItem As MailItem
    Dim olReply As MailItem
    Set olItem = Application.ActiveInspector.CurrentItem
    Set olReply = olItem.Reply
    olReply.Attachments.Add olItem
    olReply.Display
End Sub

Assign this macro to a button or keyboard shortcut. It attaches the original email as a file, preserving all attachments. Test it on a sample email first.

Adjust Default Reply Behavior In Registry

For Outlook desktop, you can tweak the registry to keep attachments on reply. This is advanced and risky—back up your registry first.

  1. Close Outlook.
  2. Press Win+R, type “regedit,” and hit Enter.
  3. Navigate to HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences (replace 16.0 with your version number).
  4. Create a new DWORD value named “IncludeAttachmentsInReply.”
  5. Set it to 1.
  6. Restart Outlook.

This setting forces Outlook to include attachments in replies. It may not work in all versions, and Microsoft doesn’t officially support it. Use at your own risk.

Common Problems And Fixes

Even with the right method, issues arise. Here’s how to solve them.

Attachments Disappear After Sending

If attachments vanish after you send, check these:

  • Your email server might block large files. Compress them or use a cloud link.
  • Outlook’s attachment size limit is 20-25 MB. Split large files.
  • The recipient’s server might reject certain file types. Rename .exe to .txt as a workaround.

Add-In Not Showing Up

If the “Include Attachments when Replying” add-in doesn’t appear:

  • Check your Outlook version. It works on Office 365 and 2016/2019, not on older versions.
  • Reinstall the add-in from the Microsoft Store or official site.
  • Enable it in File > Options > Add-ins > Manage COM Add-ins.

Drag And Drop Not Working

If dragging fails, try these fixes:

  • Make sure both windows are visible (not minimized).
  • Use Ctrl+C to copy the attachment, then Ctrl+V in the reply.
  • Restart Outlook and try again.

Frequently Asked Questions (FAQ)

Why Does Outlook Remove Attachments When I Reply?

Outlook’s default behavior removes attachments on reply to reduce email size and prevent accidental sharing. Forwarding keeps them. This design assumes you only need the original message text in a reply.

Can I Change Outlook’s Default Setting To Keep Attachments?

There’s no built-in toggle, but you can use the registry hack (described above) or install the “Include Attachments when Replying” add-in. Both methods change the default behavior.

Does The “Include Attachments When Replying” Add-in Work On Mac?

No, this add-in is only for Windows Outlook. Mac users must use the forward trick or drag-and-drop method. Microsoft hasn’t released a Mac version.

How Do I Include Original Attachments When Replying In Outlook Web?

Use the forward method: click Forward, change the recipient to the original sender, and type your reply. Or drag attachments from the original email into the reply window. OWA doesn’t support add-ins.

What’s The Fastest Way To Keep Attachments In Outlook Mobile?

The forward method is fastest. Tap the forward icon, enter the sender’s email, and add your message. Alternatively, save the attachment to your phone and reattach it manually.

Final Thoughts

Knowing how to include original attachments when replying in Outlook saves you from frustrating extra steps. Whether you use the forward trick, an add-in, or manual drag-and-drop, each method works for specific situations. Test a few to find your favorite.

Remember, Outlook’s default is to strip attachments on reply. Don’t let that catch you off guard. Bookmark this guide for quick reference, and share it with coworkers who struggle with the same issue.

If you run into problems, revisit the troubleshooting section. Most issues are easy to fix with a simple workaround. Now go ahead and reply with confidence—your attachments will stay put.