How to set up automatic replies in Outlook (2026 guide)

First, know which Outlook you are in

Microsoft currently ships several Outlooks: new Outlook for Windows (the redesigned app with a "New Outlook" toggle), classic Outlook for Windows (the long-standing desktop app, including Outlook for Microsoft 365, Outlook 2024 and Outlook 2021), and Outlook on the web / Outlook.com in your browser. The menus differ in each, and one whole method (rules that reply with a template) is documented only for classic Outlook. Steps below are labelled accordingly, so check which app you have before you start clicking. Using Gmail instead? See our matching Gmail auto-reply guide.

Method 1: Automatic Replies (out of office)

This is the classic vacation responder: the mail server sends one message on your behalf to anyone who emails you while it's switched on. Microsoft notes that this kind of auto-reply is "sent only once to each person who sends email to you while you're away", and that it is an Exchange Server service, so it works for Microsoft 365, Exchange and Outlook.com accounts even when your computer is off. It is not supported for Gmail, Yahoo or other POP/IMAP accounts added to Outlook (per Microsoft's automatic replies guide, retrieved 25 July 2026).

In new Outlook for Windows

1. On the View tab, select View settings.
2. Select Accounts > Automatic Replies.
3. Turn on the Turn on automatic replies toggle.
4. Optionally tick Send replies only during a time period and enter a start and end time, so the reply switches itself off.
5. Type your message under Send automatic replies inside your organization, and optionally tick Send replies outside your organization with a separate message for external senders.
6. Select Save.

In Outlook on the web and Outlook.com

1. Select Settings (the gear icon) > Accounts > Automatic replies.
2. Turn on the Turn on automatic replies toggle.
3. Optionally set a time period; during it you can also have Outlook block your calendar and decline new meeting invitations.
4. Enter your message, and tick Send replies outside your organization if external contacts should get a reply too.
5. Select Save.

One warning straight from Microsoft's Outlook on the web article (retrieved 25 July 2026): sending replies outside your organisation "will send your automatic reply to every email you receive, including newsletters, advertisements, and potentially, junk email".

In classic Outlook for Windows

1. Select File > Automatic Replies.
2. Select Send automatic replies, and optionally set a date range so it disables itself.
3. Type your message on the Inside My Organization tab (and the outside tab if you want external replies), then select OK.

If you don't see File > Automatic Replies, your account type doesn't support the feature and Microsoft points you at rules instead, which brings us to Method 2.

Honest limits: Automatic Replies is one static message per audience (inside and outside your organisation). It announces that you are away; it answers nothing. A customer asking about pricing, availability or a refund gets the same "I'm back on Monday" as everyone else, and their question is still sitting there when Monday comes. Our auto-reply email guide covers what a good holding message can and cannot do.

Method 2: a rule that replies with a template

Classic Outlook can auto-reply to incoming mail with a saved template via the Rules Wizard. Microsoft documents this for Outlook for Microsoft 365, Outlook 2024 and Outlook 2021 (see Use rules to create an out of office message, retrieved 25 July 2026); it is not documented for new Outlook or Outlook on the web.

Step 1: save a reply template

1. Start a new email and write the reply you want to send.
2. Select File > Save As.
3. In the Save as type list, choose Outlook Template (*.oft), name it, and save.

Step 2: build the rule

1. Select File > Manage Rules & Alerts, then New Rule on the E-mail Rules tab.
2. Under "Start from a blank rule", select Apply rule on messages I receive.
3. Pick conditions (for example sent only to me), or leave them blank to match every message.
4. Under actions, select reply using a specific template, click the underlined a specific template link, choose User Templates in File System, and open your saved template.
5. Add any exceptions, name the rule, tick Turn on this rule, and select Finish.

Two caveats Microsoft states plainly. First: "you must leave Outlook running" for the rule to send replies, so this method stops working the moment your PC sleeps. Second, per Microsoft's Out of Office Assistant emulation article (retrieved 25 July 2026), the rule "is designed to send the reply only one time to each sender during a session" to prevent repetitive replies; Outlook remembers who it has answered, and restarting Outlook wipes that list and starts again.

Honest limits: the matching is crude (sender, subject keywords, recipients), everyone who matches gets the identical template, and a broad rule happily fires at newsletters and automated notifications. It is best treated as a stopgap for a narrow, predictable case, not as a way to answer customers.

Method 3: automatic replies on a shared mailbox

If the address that needs an auto-reply is a business inbox like info@ or sales@ running as a Microsoft 365 shared mailbox, the setting lives in the admin center, not in Outlook. Per Microsoft's shared mailbox settings documentation (retrieved 25 July 2026):

1. In the Microsoft 365 admin center, go to Teams & groups > Shared mailboxes.
2. Select the mailbox, then select Edit under Automatic replies.
3. Tick Send automatic replies to senders inside this organization and enter the replies for people inside or outside your organisation. Microsoft notes you can't add images, only text.
4. Select Save.

Because this runs on the server, it replies whether or not anyone has Outlook open, which makes it the sensible built-in choice for a business address.

Honest limits: it needs admin access, the message is plain text, and the settings panel offers no conditions and no schedule: one static acknowledgement for every sender until an admin switches it off. "We received your email" buys goodwill for a few hours; it does not shrink the pile waiting inside the mailbox.

Method 4: an AI reply agent

Everything above sends a message about your email instead of a reply to it. The fourth option is a different category: an AI email agent that reads each incoming email, answers it from your business knowledge, and leaves anything it can't answer for a human. The sender gets their actual question addressed (opening hours, pricing, availability, next steps) rather than a promise that someone will read it later.

InReply (our product, so weigh accordingly) is built for exactly this on a business inbox. It connects to your existing Outlook or Microsoft 365 inbox via OAuth: nothing to install, no add-in, no new app for the team to adopt, no helpdesk to migrate to. Replies are grounded in a knowledge base you control, playbooks set the tone, behaviour and routing, and an actions list flags what needs a human, with urgent items called out. On every plan it starts in Ghost Mode: it only writes drafts, and you approve each send. When a playbook has earned your trust, you can enable Autopilot for it and replies go out automatically. It works like an email answering service that lives inside your own inbox, and our guide to AI email assistants for Outlook compares the wider field.

Honest limits: it is a paid tool (plans from £39/month with a 14-day free trial, no card required), it needs a knowledge base worth answering from, and it is aimed at business inboxes with real inbound volume, not at covering one person's week off. For a fortnight's holiday, Method 1 is free and fine.

Which Outlook auto-reply should you use?

The short version: use Automatic Replies for personal absence, the shared mailbox reply for a simple acknowledgement on a team address, a rule only when the other two aren't available or you need a narrow trigger, and an AI reply agent when the goal is answered customers rather than notified ones.