How to Set Automatic Replies in Outlook Online (Out of Office)

Last week I was getting ready for a few days off, and I almost forgot the one thing that saves me the most stress: an out-of-office reply. Two minutes in Outlook, and nobody wonders why I’m quiet.

In this tutorial, I’ll show you how to set automatic replies in Outlook Online, schedule them for the exact days you’re away, write one message for coworkers and another for customers, check that it works, and turn it off again.

I tested every step in my test work mailbox for my made-up business, Bluebird Landscaping Co.

Method 1: Turn on automatic replies in Outlook on the web

Automatic replies live in the Account part of Settings now, not under Mail like older guides say. If you haven’t poked around there before, it’s the same area where you check your storage space in Outlook Online.

1. Open Outlook on the web and click the Settings (gear) icon at the top right. In a narrow window, the gear moves into the … menu next to the bell.
2. Select Account, then Automatic replies.
3. Switch the Automatic replies toggle on.

Before you flip the toggle, the page says “Turn on automatic replies to let people know you’re away.” The options below it stay greyed out until the toggle is on.

How does this work?

The middle column lists Email account, Shared with me, Automatic replies, Signatures, Categories, and Storage. Once the toggle is on, Outlook answers incoming mail with your message. Nothing is sent until you click Save at the bottom, so you can set everything up first.

Method 2: Schedule your out-of-office dates

I like a start and end date, so I can set the reply days ahead and forget about it. Microsoft says that if you skip this, the reply stays on until you turn it off yourself.

1. Check Send replies only during a time period.
2. Pick a Start time date and time.
3. Pick an End time date and time.

For my test, I picked a start of 10/25/2026 at 12:30 AM and an end of 10/30/2026 at 5:00 PM. Each date opens a small calendar, and the time list moves in 30-minute steps.

How does this work?

Right under the dates, a During this time section has three checkboxes: Block my calendar, Automatically decline new invitations, and Decline and cancel my meetings. I left them unchecked in my test. If you’d rather keep the event details to yourself, you can mark an event private in Outlook Online.

Pro tip: Set the end time to the evening before you’re back, not the morning you return. That way, people who write on your first day get a real answer instead of an “I’m away” note.

Method 3: Write different messages for coworkers and outside senders

This is the part that makes a reply useful. In my work mailbox, Outlook shows two message boxes: one for people inside my organization and one for everyone else.

1. Type your message in Send automatic replies inside your organization. This box is required.
2. Leave Send replies outside your organization checked if customers and vendors should get a reply. It was checked by default for me.
3. Check Send replies only to contacts if you only want people in your contacts to get it.
4. Type the outside message in the second box.
5. Click Save.

Here’s what I wrote for my coworkers: “Hi, thanks for your email. I’m out of the office Monday, October 26 through Friday, October 30, 2026. For this week’s crew schedules, please check the shared Crew schedules folder. I’ll reply when I’m back on Monday, November 2.”

Customers got a shorter one: “Thanks for contacting Bluebird Landscaping Co. I’m away until Monday, November 2, 2026, and will answer your message when I’m back. For quotes and scheduling, please call our office during business hours.”

How does this work?

The inside message can mention internal folders and names. The outside one shouldn’t. Both boxes have a formatting toolbar, so you can add bold text or a link. If you want to pick a different look, you can also change the fonts in Outlook Online.

Pro tip: Microsoft warns that replying to everyone outside your organization also answers newsletters and junk mail. If that bugs you, turn on Send replies only to contacts.

Method 4: Check that your automatic reply actually works

I never trust a setting until I see it work. After I clicked Save, a notice showed up that said “Automatic replies are currently turned on,” with a Turn off link. It came back each time I opened the mailbox, which is a nice reminder.

Next, I started a new email to the mailbox that had replies on. Before I even sent it, a banner above the Send button showed the start of my automatic reply, with a Show more link.

Then I sent a test email to myself called “Crew schedule question – week of Oct 26, 2026.” Within seconds, the conversation showed “sent an automatic reply” with my inside-organization message.

How does this work?

The banner is handy for coworkers, because they know you’re out before they hit Send. I only saw it for an address in my own organization. While you’re away, an inbox rule in Outlook Online can also sort the mail that piles up.

Method 5: Turn off automatic replies when you’re back

If you set an end time, the replies stop on their own. If you didn’t, turn them off by hand. There are two ways:

• Click Turn off in the “Automatic replies are currently turned on” notice.
• Go to Settings > Account > Automatic replies and switch the toggle off.

I used the Turn off link. When I opened Settings again, the toggle was off and the time period had reset to its defaults.

Set up automatic replies in new and classic Outlook for Windows

I didn’t test these, so here are the steps Microsoft lists. In new Outlook for Windows, go to the View tab, select View settings, then Accounts > Automatic Replies. The toggle and options match the web.

In classic Outlook, select File > Automatic Replies, then Send automatic replies. Add an optional date range, write your messages on the Inside My Organization and Outside My Organization tabs, and click OK.

To stop, select Turn off in the bar under the ribbon. You can also download emails from Outlook before a long trip.

Things to keep in mind

• Work vs personal accounts. Microsoft lists the same Settings > Account > Automatic replies steps for Outlook on the web and Outlook.com. The inside and outside organization options are for work or school accounts.
• Gmail and Yahoo accounts. Microsoft says automatic replies aren’t supported for Gmail, Yahoo, or other POP or IMAP accounts added to Outlook.
• One reply per person. Microsoft says the message goes once to each person who emails you while you’re away. I didn’t test repeat emails.
• Calendar options. Block my calendar and the two decline options can change your meetings, so read them before you check them. I didn’t test them.
• Keep it short. Say when you’re back and who can help. Skip personal details like travel plans. For a sensitive handoff, you can make an email confidential in Outlook Online.

Want to tidy up more of your Outlook mailbox? Start here

• Block a sender in Outlook Online
• Set calendar reminders in Outlook
• Forward multiple emails at once
• All Outlook Online tutorials

An automatic reply handles incoming mail while you’re away, but it won’t send anything new for you. For that, learn how to schedule an email in Outlook so your message goes out at the time you pick.

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