Need help setting up an Out of Office reply in Outlook

General
1

I’m going on vacation soon and want Outlook to automatically send an Out of Office reply, but I’m confused by the settings and different versions (desktop app vs web). I’d like step-by-step guidance on how to set this up correctly so that coworkers and clients get the right message while I’m away.

2

Here is the short version so you can set it and go on vacation.

First, figure out which Outlook you use:
• Outlook desktop on Windows (connected to Exchange or Microsoft 365)
• Outlook on the web (OWA in a browser)
• Outlook desktop with a simple POP/IMAP account like Gmail

I will hit all three.

  1. Outlook desktop, Microsoft 365 or Exchange account
  1. Open Outlook.
  2. Go to File, then click Automatic Replies.
  3. Select Send automatic replies.
  4. Turn on Only send during this time range if you want a start and end date.
  5. In the Inside My Organization tab, type your internal message.
    Example:
    Subject: Out of Office
    Message:
    I am out of the office from Feb 10 to Feb 20. I will not check email. For urgent issues contact John Doe at john.doe@company.com.
  6. Click the Outside My Organization tab.
  7. Check Auto-reply to people outside my organization if you want external replies.
  8. Type a simpler external message.
  9. Click OK.

Your server handles these replies even when your PC is off.

  1. Outlook on the web (Office 365 / OWA)
  1. Open a browser and go to outlook.office.com.
  2. Sign in.
  3. Click the gear icon in the top right.
  4. Click “View all Outlook settings” at the bottom.
  5. Go to Mail, then Automatic replies.
  6. Turn on Automatic replies.
  7. Check “Send replies only during a time period” if you want start and end dates.
  8. Enter your message in the box.
  9. Check “Send replies outside your organization” if you want external replies.
  10. Optionally use a shorter message for externals.
  11. Click Save.
  1. Outlook desktop with POP/IMAP accounts like Gmail

This part is annoying.

Outlook does not send server-side automatic replies for POP or standard IMAP. Your computer must stay on with Outlook running.

Steps:

  1. Create a template:
    1. New Email.
    2. Type the OOO text.
    3. Click File, then Save As.
    4. Save as Outlook Template (*.oft). Name it OOO.oft.
  2. Create a rule:
    1. File, Manage Rules & Alerts.
    2. New Rule.
    3. Start from a blank rule, select “Apply rule on messages I receive”.
    4. Next.
    5. Do not pick conditions if you want all mail. It will ask you to confirm. Click Yes.
    6. Under “What do you want to do”, check “reply using a specific template”.
    7. Click “a specific template”.
    8. Choose “User Templates in File System”.
    9. Pick your OOO.oft template.
    10. Next.
    11. Add exceptions if needed. For example to skip mailing lists.
    12. Next.
    13. Name the rule, for example Out of Office.
    14. Check “Turn on this rule”.
    15. Finish.

Leave Outlook open while you are away. If Outlook closes, replies stop.

Good practice for the auto reply text:

Internal:
• Clear dates
• Availability of email and phone
• Backup contact with name and email

External:
• Clear dates
• Short and neutral
• Optional contact address like info@company.com

Example internal:
I am out of the office from Feb 10 to Feb 20 with no email access.
For urgent issues contact Jane Smith at jane.smith@company.com.
I will respond after Feb 21.

Example external:
I am out of the office until Feb 20 and will respond after I return.
For urgent matters email support@company.com.

If you use both desktop and web with Microsoft 365, set it in one place. The setting syncs to the other.

3

Couple of extra angles to add on top of what @kakeru wrote, since Outlook loves to be confusing:

1. Quick way to tell WHICH Outlook you’re actually using

Before touching settings, check this, or you’ll be hunting in the wrong place forever:

  • If you open Outlook in a browser and the address bar says outlook.office.com → Outlook on the web.
  • If it is a program on Windows and the top-left says “File” and has a green/blue Outlook icon → classic desktop Outlook.
  • If your company just pushed “New Outlook” on Windows:
    • There is no “File → Automatic Replies.”
    • You have a simplified UI and a toggle at the top-right that says “New Outlook.”
    • Automatic replies are usually under
      Settings (gear) → Mail → Automatic replies, very similar to Outlook on the web.

I don’t totally agree with the idea that you need to set it separately on desktop and web for Microsoft 365. In most orgs, if your account is Exchange Online / Microsoft 365, the setting is stored on the server, so changing it in either place updates the other. I usually tell people: pick the UI you like better and do it there once.

2. Things people forget that bite them later

  1. Start & end times
    If you’re leaving at noon on the 10th but you set it to start on the 11th, anyone emailing the first day gets no OOO. I usually:

    • Start: the morning of my last working day or the actual time I leave
    • End: the morning I’m back, not midnight, to avoid that weird “I’m back but my OOO is still on” half-day.

  2. Different internal vs external behavior
    @kakeru suggested shorter external text, which is fine, but I’d actually:

    • Put very clear dates in both.
    • For externals, specify if replies may be delayed even after you return.
      Example: “I’m back on Feb 21 but catching up, so replies may be delayed.”

  3. Distribution lists and shared mailboxes
    If you’re also responsible for:

    • support@...
    • info@...
      That mailbox might need its own auto reply. Logging into that mailbox (web is easiest) and setting Automatic replies there is usually required. A ton of people forget this and come back to 300 “did you get my email?” messages.

  4. Mobile app confusion
    Outlook mobile can change your automatic replies, but the UI is clunky and changes often. I actually recommend avoiding the phone for this so you don’t end up thinking you set it, when it didn’t save or only applied to one account.

3. If you’re forced to use the “New Outlook” on Windows

This is where a lot of folks get stuck lately.

Rough path (Microsoft keeps tweaking, so menu names may be slightly off):

  1. Open New Outlook.
  2. Click the gear icon in the top right.
  3. Click “View all Outlook settings.”
  4. Go to Mail → Automatic replies.
  5. Turn on automatic replies.
  6. Choose time range, write message, etc.
    Same logic as Outlook on the web.

It’s basically just a wrapper around the web settings. That’s why I personally just open a browser and do it there; less UI drama.

4. Making sure it actually works

Whichever flavor you use:

  1. After turning it on, send yourself a test from:
    • Your personal email (Gmail/Yahoo/etc.) to check external replies.
    • A coworker’s account (if possible) to check internal.
  2. Wait a minute; some systems take a little to trigger the first auto reply.
  3. Note: Outlook typically sends one auto reply per sender per “session” so you won’t see a reply every single time you email yourself.

If you’re on POP/IMAP like @kakeru explained, I 100% agree it’s annoying, but I’ll add this: if your PC might sleep, the rule-based OOO is unreliable. In that case, sometimes it’s cleaner to set a vacation responder directly in Gmail (or whatever service) instead of relying on Outlook’s rule.

5. Simple template text you can tweak fast

Internal:

I’m out of the office from [date] to [date] and not checking email.
For urgent issues, contact [backup person] at [email] / [phone].
I’ll reply after [return date].

External:

I’m out of the office until [date] and may be slow to respond after I return.
If your matter is urgent, please contact [team or shared address].

If you post which version you’re actually seeing on screen (desktop old, desktop “New Outlook,” or just the website) and what kind of account (work 365, personal Outlook.com, Gmail in Outlook, etc.), can walk through the exact clicks so you don’t have to spelunk through 6 different settings pages.

4

Couple of gaps I’d fill on top of what @caminantenocturno and @kakeru already covered:

  1. You do not always need to touch every Outlook you use
    They’re right that Microsoft 365 / Exchange auto replies are server based. Where I slightly disagree is in how often you should jump between desktop and web. In most corporate setups, you can safely:

    • Set the Out of Office in one place (classic desktop, New Outlook, or web).
    • Trust it to sync, then just test from another account.
      Constantly checking multiple UIs adds confusion and doesn’t really buy you extra reliability.

  2. Use your calendar to avoid mistakes
    Easiest way to not mis-type dates:

    • Open your Outlook calendar first.
    • Look at the exact “Out of office” event you created.
    • Copy/paste those dates into the OOO message and time range.
      This avoids the classic “my message and my automatic reply dates don’t match” issue.

  3. Control who actually gets a reply
    The built in automatic reply setting is all or nothing for internal/external. If you want more control:

    • In Outlook desktop, add an extra rule:
      • Condition: “sender is in specified Address Book” or “sender’s address contains @clientdomain.com”.
      • Action: forward to a colleague or a shared mailbox instead of relying only on the generic OOO.
        This is handy if you have VIP customers that should never just hit a dead end.

  4. For POP/IMAP: consider not using Outlook at all for OOO
    I fully agree with both that rules-based replies on POP/IMAP are a pain. My twist:

    • If the account is Gmail, Yahoo, or similar, it is almost always more reliable to set the vacation responder directly in the webmail and skip Outlook’s template/rule dance completely.
    • Outlook then just becomes a viewer; your auto reply lives on the provider’s servers.

  5. Avoid OOO loops and spam issues
    People rarely think about the downsides:

    • Mailing lists and automated systems can get spammed by your OOO if you reply to every message.
    • Use exceptions in rules (or avoid rules entirely if you can rely on server OOO) so you do not respond to newsletters, “no reply” addresses, or ticketing systems.
      This keeps your domain’s reputation cleaner and avoids weird reply chains.

  6. Best practice message content that actually helps people
    The examples given are solid. One tweak I strongly recommend:

    • Explicitly state what will not happen.
      Example:
      “Emails received during this period will not be monitored. If your matter is still relevant after [return date], please resend your message.”
      It trains people not to assume you saw everything during your vacation.

  7. Pros & cons of relying on Outlook’s native automatic replies
    Pros:

    • Integrated with calendar and mailbox.
    • On Microsoft 365 / Exchange it runs 24/7 on the server, even if your PC is off.
    • Lets you split internal vs external messages, which improves clarity.

    Cons:

    • Interface and location of the setting change depending on classic desktop, New Outlook, and web, which confuses many.
    • POP/IMAP accounts get a clunky, rules-based workaround that breaks if your machine goes to sleep.
    • Easy to misconfigure dates or forget about shared mailboxes and lists.

If you post a screenshot of the top bar of Outlook (hiding any private info), it is possible to point you to the exact clicks for that specific flavor so you can set it once, test it, and then go enjoy your vacation without fiddling through menus again.