How to reply with attachments in Outlook

Outlook's Reply and Reply all leave the original attachments behind. There is no setting that changes it. Forward keeps the files, but hands you an empty recipient line — so you retype everyone who was on the thread. The fastest fix without an add-in is to copy the attachments out of the original message and paste them into your reply; the fastest fix altogether is a ribbon button that does it for you.

Why Outlook drops the attachments when you reply

This is deliberate. Microsoft's own support answer says it plainly: when you reply, Outlook assumes the person on the other end already has the files they sent you, so it leaves them out. Reply all inherits the same assumption — and that is where it falls apart, because the people you just added to the thread have never seen those files. Forward was built for passing a message on, so it takes the attachments with it.

That split explains everything below. Every workaround on this page is a way of borrowing Forward's behaviour for a reply.

The three manual ways — and what each costs you

Forward instead of reply

1. Open the message and choose Forward. The attachments come with it.
2. Delete the FW: from the subject line, or the thread breaks in two.
3. Enter every recipient by hand — everyone who was in To, everyone who was in Cc.
4. Send.

What it costs: the recipient list. On a thread with eight people on Cc, this is where mistakes happen — one name missed, and somebody drops out of the conversation without ever knowing it.

Copy the attachments into the reply

1. Click Reply or Reply all, so the recipients are filled in for you.
2. Open the original message in its own window next to it.
3. Select the attachments there, copy them (Ctrl+C, or ⌘C on a Mac), click into the body of your reply and paste.
4. Check the count before you send — inline images can be skipped silently.

What it costs: two windows and a check. It is the quickest of the three when your Outlook build supports it, and the one most likely to behave differently after an update.

Save to disk and re-attach

1. Save the attachments from the original message into a folder.
2. Click Reply or Reply all.
3. Add the saved files back to the reply.
4. Clear the folder out afterwards — this is how confidential files quietly accumulate in Downloads.

What it costs: time, and a copy of the files on disk you never asked for. It is also the only route that works everywhere, every time, which is why people do it three times a day and call it normal.

How to reply all with attachments

Same answer, higher stakes. Reply all drops the attachments as well, and here it actually costs something: the colleagues you are pulling into the thread never received those files in the first place.

Outlook has no Reply all with attachments command. What you will find recommended instead is this setting:

File → Options → Mail → Replies and forwards → When replying to a message → Attach original message.

Read it carefully before you rely on it. It attaches the original email as a message file — your recipients get an email inside an email, and they have to open that before they reach the PDF. It is not the same as replying with the files attached, and to an external recipient it looks like a slip.

So for Reply all, the working options are the three above, applied to Reply all instead of Reply — and the one most people fall back on is Forward, which means rebuilding the recipient list by hand every time. VBA macros and add-on toolkits are the other standing suggestion; macros are blocked outright in most managed tenants, and both are a heavier commitment than the problem deserves.

Keeping attachments when replying — the short answer

No, Outlook cannot keep the attachments in a reply on its own. No setting, no checkbox, no version.

To keep them you have three choices: move the files across by hand, forward instead of replying and rebuild the recipient list, or add a button that does it for you. That is the complete list. Everything else you will read online is one of those three in a different costume.

Does this work in new Outlook, Outlook on the web, and on Mac?

Outlook behaves the same way everywhere: Reply and Reply all leave the original attachments behind in classic Outlook on Windows, in new Outlook, in Outlook on the web and on a Mac. The workarounds differ in the details — the Attach original message setting lives in the classic desktop client, and copy-and-paste of attachments is the least predictable step across builds.

The add-in follows the same rule. It runs in classic Outlook on Windows, in new Outlook on Windows, in Outlook on the web and in Outlook on Mac. It does not appear in Outlook on Android or iOS — the mobile ribbon isn't part of what it installs.

Two things decide whether you see it at all: your mailbox has to be on Exchange — Microsoft 365, or Exchange Server 2016 or later — and your Outlook has to be 2016 or later. That also rules out POP3 and IMAP accounts, which cannot run any Outlook add-in. Neither of those is our choice; it is how Microsoft draws the line, and no add-in on the Marketplace gets around it.

If it runs in your Outlook, it runs the same way in all of them.

The one-click way: two buttons in the ribbon

If you do this more than once a week, the honest recommendation is to stop doing it by hand.

Using the old “Reply with attachment” add-in and the buttons stopped working?

If you installed Reply with attachment — the older one, singular — and its buttons now do nothing at all when you click them, here is what happened.

That add-in works through Exchange Web Services. Microsoft switched off the legacy tokens EWS add-ins depend on: “Legacy Exchange Online user identity tokens and callback tokens are no longer supported and turned off across all Microsoft 365 tenants.” That change began in February 2025, which is why the buttons can fail without an error message — the request is refused before it ever reaches your mailbox. EWS itself is being phased out from 1 October 2026 and switched off for good on 1 April 2027. Mailboxes on Exchange on-premises are not affected.

There is nothing to repair on your side. The replacement is Reply with attachments — plural, a separate Marketplace listing with its own name and logo, running on Microsoft Graph instead of EWS. The buttons you know are still there, now reading Reply with Attachments and Reply All with Attachments — and they work.

Get Reply with attachments →

Rolling this out for a company? Your admins can deploy it centrally via Integrated apps →