How to Reply With Attachments in Outlook (Classic, New Outlook, Web, Mac and Mobile)

When you click Reply or Reply All in Outlook, the files from the original email do not come with it. Forward keeps them, but then you lose the people in To and Cc. In this guide, I’ll show how to reply with attachments in Outlook on each client: classic Outlook for Windows, new Outlook, Outlook on the web, Mac and the mobile app.

Quick Answer: Outlook never adds the original attachments to a reply. Click Reply, pop the reply out into its own window, then drag the files from the original message into it (or use Attach File). Classic Outlook can also attach the whole original message to every reply. Forward keeps the files, but you have to copy the recipients over.

Why Outlook Drops Attachments When You Reply

This is by design. A reply goes back to the person who sent you the file, so Microsoft leaves it out. Forward keeps attachments because it goes to someone new. Microsoft explains this on its reply and forward support page.

The problem starts when you reply to a group and some of them never got the file, or when you add a new person to Cc halfway through the thread. Then you need the attachments back in the reply.

Here is an email with attachments that we want to keep in the reply.

After clicking Reply, the draft has the full mail trail but no attachments.

No Outlook client has a built-in “Reply with attachments” button, so pick one of the methods below.

Method 1) Reply, Then Add the Files Back

This keeps all the recipients, the RE: subject and the thread. It is the method I would use most of the time.

Classic Outlook for Windows

1. Select the email and click Reply or Reply All.
2. If the reply opens inside the Reading Pane, click Pop Out so it opens in its own window. Now you can see the original message and the reply side by side.
3. Drag each attachment from the original message into the reply window.
4. Or right-click one attachment in the original, choose Select All, press Ctrl+C, then click in the reply and press Ctrl+V. This copies all of them in one go.
5. If the files are saved on your PC, use Message > Attach File > Browse This PC in the reply instead.

When dragging and pasting both fail, read why copy and paste fails in Outlook. It is usually a clipboard or add-in problem, not the attachment.

New Outlook for Windows and Outlook on the Web

The two work the same way here.

1. In the original email, open the attachment’s menu and choose Download all, or Download for a single file. Save to OneDrive is there too.
2. Click Reply or Reply All.
3. In new Outlook, select Attach File on the Message tab and pick the saved files with Browse. In Outlook on the web it is Attach > Browse this computer.
4. You can also drag the files from File Explorer into the reply. Outlook shows a “Drop files here” hint.

If you saved the files to OneDrive, pick them from the OneDrive option instead. Outlook then asks whether to share a link or attach a copy. A link keeps the email small, but check who it gives access to before you send.

Method 2) Forward, Then Copy the Recipients Back

Forward keeps every attachment, so this is the quickest route when there are many files.

1. Select the email and click Forward.
2. Add the original sender, then copy the addresses from the original email’s To and Cc lines and paste them into the same fields of the forward.
3. If you want it to look like a reply, change FW: to RE: in the subject.

Two downsides. You can miss a Cc person on a long thread, and the recipients see a forward header, not a normal reply. For a thread with 10 or more people, I would use Method 1 instead.

Method 3) Attach the Whole Original Message (Classic Outlook Only)

Classic Outlook has a setting that attaches the full original email, with its attachments inside, to every reply.

1. Go to File > Options > Mail.
2. Scroll down to Replies and forwards.
3. Change When replying to a message from Include original message text to Attach original message.
4. Click OK.

Now each reply carries the original as an attached Outlook item. The recipient opens it to see the earlier message and its files.

Be careful with this one. It applies to all your replies until you change it back, and the mail trail no longer shows in the body. The attachment is an Outlook message file, so people on other mail apps may not open it easily.

Each round of replies also nests one message inside another. Microsoft lists all the options on its change how the original message appears page.

New Outlook and Outlook on the web do not have this setting. The nearest thing is Forward > Forward as attachment (click the drop-down arrow next to Forward), which attaches the original email to a new forward. Classic Outlook has it under More Respond Actions > Forward as Attachment.

Outlook for Mac

Outlook for Mac has no option to keep the attachments in a reply either.

1. Double-click the original email so it opens in its own window.
2. Click Reply or Reply All. The reply opens in a separate window.
3. Drag the attachments from the original window into the reply.

To add files from your Mac, click Attach File and choose Browse this Mac, OneDrive or Recent Files. You can also drag a file from Finder. In legacy Outlook for Mac, Attach File is on the Message tab. Microsoft says support for legacy Outlook for Mac ends in October 2026, so the new Outlook for Mac steps are the ones to learn.

Outlook for iPhone and Android

The mobile app also drops attachments on reply, but you no longer need to save the file to your phone first.

1. Open the email with the attachment.
2. Tap the three-dot menu in the message and copy the attachment.
3. Tap Reply, then paste the attachment into the reply.

This works for normal attachments, not for OneDrive or SharePoint links. To send the whole original email instead, tap the paperclip in the reply and choose Attach email.

Add-ins for Reply With Attachments

If you reply with attachments every day, an add-in saves these steps. Check which Outlook you use first.

• COM add-ins (the old desktop type) only work in classic Outlook for Windows. New Outlook does not run them. For example, IvaSoft’s ReplyWithAtt adds the original files to every Reply and Reply All, but its own page says it does not support new Outlook.
• New Outlook and Outlook on the web only run web add-ins from More apps > Add apps. In classic Outlook the store is under Home > All Apps (older builds show Get Add-ins).

On a work account, admins decide which add-ins users can install. If the store option is missing, ask IT before looking for a workaround.

When the Reply With Attachments Will Not Send

Adding the files back can push the email over the size limit. In Exchange Online the default is 35 MB to send and 36 MB to receive. Admins can raise it up to 150 MB. Outlook on the web allows about 25% less than the configured limit, because files grow by roughly a third when encoded for sending. The Outlook mobile app stops at 33 MB per message. All of this is on Microsoft’s Exchange Online limits page.

So if a reply with three large PDFs bounces with a non-delivery report, share them from OneDrive as links instead of attaching copies. Remember that every attachment you send also stays in your Sent Items. If your mailbox is getting full, here is how to see your Outlook mailbox size.

Other attachment problems have their own fixes:

• The Attach File button does nothing or gives an error: see can’t attach file in Outlook.
• Outlook hangs when you add a file: see Outlook freezes when attaching files.
• You want to send a whole folder: here is how to attach a folder in Outlook.

If you only need one or two files in a reply, Method 1 is enough. Use the Attach original message setting only if your recipients also use Outlook, and switch it back when you are done.