How do I set up an automatic reply in Outlook step by step?

General
1

I need help setting up an automatic reply in Outlook for when I’m out of the office. I’m confused by the different settings for rules, out-of-office messages, and different versions of Outlook, and I don’t want to miss important emails from clients. Can someone walk me through the exact steps to create a proper auto reply that works reliably?

2

Here is the straight version so you do not miss stuff.

First, figure out which Outlook you use.

  1. Outlook for Microsoft 365 or Outlook 2019/2016 (desktop, with Exchange/Office 365)

Step 1
Open Outlook.
Click File in the top left.

Step 2
Click Automatic Replies.
If you see “Out of Office Assistant” it is the same thing.

Step 3
Select “Send automatic replies”.
Check “Only send during this time range” if you know start and end dates.
Set your From and To times.

Step 4
There are two tabs in the big text box.
Inside My Organization
Outside My Organization

Type something like:

Inside My Organization:
Subject: Out of Office
Body:
Thanks for your email. I am out of office from Feb 10 to Feb 15.
I have limited access to email.
For urgent issues contact Alex Smith at alex.smith@company.com.

Outside My Organization:
Shorter, less detail.
You can also uncheck “Auto-reply to people outside my organization” if you do not want to reply to external senders.

Click OK. You are done.
When the time window ends, Outlook stops the replies.

  1. Outlook desktop with POP/IMAP (no Automatic Replies button)

You need a rule plus a template.

Step 1, create the template
Home tab.
New Email.
Type your out of office message.
Click File, then Save As.
In “Save as type”, pick “Outlook Template (*.oft)”.
Give it a name like “OOO.oft”.
Save.

Step 2, create the rule
Home tab.
Click Rules.
Click “Manage Rules & Alerts”.
Click “New Rule”.

Under “Start from a blank rule”, pick “Apply rule on messages I receive”.
Click Next.

Choose conditions if you want, or leave all unchecked to apply to all mail.
Click Next.
Outlook warns it will apply to all messages. Click Yes.

Under actions, check “reply using a specific template”.
Click the link “a specific template”.
Change “Look In” to “User Templates in File System”.
Pick your OOO.oft template.
Click Open, then Next.

Add exceptions if you want, for example
“except if from people or public group” to skip internal system accounts.
Click Next.

Name the rule “Out of office auto reply”.
Check “Turn on this rule”.
Click Finish, then OK.

Important:
Your Outlook must stay open and your computer must stay on for this type of rule to work.

  1. Outlook on the web (Outlook.com or Office 365 web mail)

Step 1
Log in in a browser.
Click the gear icon in the top right.
Click “View all Outlook settings”.

Step 2
Go to Mail, then Automatic replies.

Step 3
Turn on automatic replies.
Set the time range if needed.
Type your message.
Check “Send replies outside your organization” if you want to.
Use a separate text box for external if the option shows.
Click Save.

  1. Keep messages from being missed

Use clear info in your message:
• Exact dates you are away.
• If you check mail or not.
• Backup contact name, email, phone.
• For clients, say if response times will be slower.

Example:

Subject: Out of office

I am out of office from Feb 10 through Feb 15.
I will not read email during this time.
For urgent issues, contact Alex Smith, alex.smith@company.com, 555 123 4567.
I will reply after Feb 16.

  1. Quick troubleshooting

If people say they do not get replies
• Check if you limited replies to “My Organization” only.
• Check date range.
• If you used a rule, make sure Outlook is open.
• Check if the message landed in their spam.

If you share which exact Outlook version and email type you use (Exchange, Microsoft 365, Gmail via IMAP, etc), you can get more precise steps.

3

You’re not wrong to be confused; Outlook did a great job of making one simple thing exist in three different places.

@shizuka already nailed the classic “click here, then here” steps, so I’ll skip retyping those and focus on helping you pick the right method and avoid missing messages.

1. First: figure out which type of auto reply you actually need

There are really two different tools:

  1. Server-based Out of Office / Automatic Replies

    • Good for: “I’m on vacation, reply to everyone automatically.”
    • Works even if your computer is off.
    • This is the one you use if you see an Automatic Replies button (or Out of Office Assistant).

  2. Rules-based auto reply

    • Good for: more specific stuff.
    • Examples: reply only to clients, only to a certain project alias, or send different text based on who writes you.
    • Requires Outlook to stay open.

If you’re just trying not to miss things while you’re away, you almost always want #1 if it’s available in your setup.

2. Quick way to tell what you have

In the desktop Outlook app:

  • Click File
    • If you see Automatic Replies, you’re on Exchange / Microsoft 365 and can use the real out-of-office feature.
    • If you only see Rules & Alerts and no Automatic Replies, you’re on POP/IMAP and have to use a rule + template like @shizuka described.

In a browser:

  • If you use Outlook through your company’s Microsoft 365 portal, you’re in Outlook on the web, which has its own Automatic replies setting under the gear icon.

If you’re still not sure: ask yourself whether you log into Outlook in a browser with a work account. If yes, 99% chance you have server-side automatic replies.

3. How to combine Automatic Replies + Rules without chaos

This is where a lot of people get tripped up.

If you:

  • Turn on Automatic Replies, and
  • Also create a rule that auto-replies to everything

…you can end up double-responding or sending weird templates.

Decent pattern that keeps it sane:

  1. Use Automatic Replies for the generic “I’m gone from X to Y” message.
  2. Use rules only for special cases, like:
    • Forward all mail from VIPs to a colleague.
    • Flag and move certain messages so they’re easy to find when you’re back.
    • Stop auto responses to certain addresses (like no-reply systems).

Example rule combo with out-of-office turned on:

  • Condition: “from” specific client domains
    Action: forward to your backup person
    Result: they still get your out-of-office response, and your coworker gets a copy to handle urgently.

You don’t need a reply rule at all if the Automatic Replies feature is available and you just want a standard OOO.

4. How not to miss important mail while you’re gone

The auto reply only tells people you’re away. It doesn’t help you triage. Do this too:

  1. Make a “While I was out” folder

    • Create a folder called something like !While I Was Out.
    • Set a rule:
      • Condition: from your most important contacts / domains
      • Action: copy (or move) to that folder
    • That way, when you get back, you check that folder first instead of digging through 800 random newsletters.

  2. Forward real emergencies

    • Rule:
      • Condition: subject contains words like “urgent”, “P1”, or from your manager / key clients
      • Action: forward to your backup person and maybe mark as high importance.
    • Pair that with an automatic reply that tells them who the backup is and how to reach them.

  3. Stop infinite loops

    • If two systems auto-reply to each other, it can get stupid fast.
    • Avoid setting rules that reply to all mail when you’re already using Automatic Replies.
    • If you must use a rule-based reply, add an exception like:
      • “except if the subject contains ‘Out of Office’ or ‘Auto Reply’”
    • That reduces reply storms.

5. A simple “choose your path” guide

  • You use work email with Microsoft 365 or Exchange, and you just want a basic vacation reply
    ⇒ Use Automatic Replies only. No rule needed.

  • You use Outlook with Gmail / Yahoo / basic ISP account and no Automatic Replies button
    ⇒ Use the template + rule method like @shizuka laid out, but remember Outlook has to stay open.

  • You want different messages for internal vs external and have Microsoft 365 / Exchange
    ⇒ Use Automatic Replies and fill in both “inside my organization” and “outside my organization.”
    You do not need rules just to do that.

  • You need more control: only certain people get an auto reply, others just get silently forwarded or handled
    ⇒ Turn on Automatic Replies as your default message, then add rules for the special logic (forwarding, flagging, exceptions).

6. Minimal text you can reuse

Internal:

Subject: Out of Office
I’ll be out of the office from [date] to [date] and will not be checking email regularly.
For urgent issues, contact [name] at [email] / [phone]. I’ll respond after [date].

External:

Subject: Out of Office
I’m currently out of the office until [date].
For urgent business matters, please contact [name] at [email].
Your message will be reviewed when I return.

Swap in your dates and backup contact and you’re set. If you share which exact Outlook (desktop vs web) and whether it’s company 365 or something like Gmail/IMAP, people here can tell you literally which clicks to make on your screen so you don’t have to guess again.

4

You already have the “how” from @shizuka and the “when to use what” logic from @byteguru, so I’ll fill in the gaps they skipped: how not to shoot yourself in the foot once the automatic reply is on.

1. The part most people miss: test your setup

After you turn on any Out of Office / rule:

  1. Send yourself a test from:
    • Your work account (internal).
    • A personal account like Gmail (external).
  2. Check:
    • Did you get exactly one auto reply per sender, not multiple?
    • Did the internal vs external wording look right?
    • If you set a time range, does Outlook show “Automatic Replies” banner only inside that range?

If you use rules instead of server automatic replies, close Outlook, send yourself a mail, and confirm that no reply is sent. That tells you the rule really requires the app to be open, which is the main drawback of that method.

2. Decide how “loud” your auto reply should be

Something I actually disagree with a bit from the other answers: replying automatically to everyone outside your organization is not always ideal.

You might want to:

  • Turn off external replies if:

    • You subscribe to a lot of newsletters or automated systems.
    • You work in security sensitive environments where leaking travel info is frowned upon.

  • Keep external replies on but stricter:

    • Only send them to people in your Contacts (there is an option for this in some Outlook versions).
    • Keep the external message very short and without travel dates if that matters.

So, not “on or off” globally, but “what is my risk vs benefit.”

3. Avoid messy subjects and weird threads

Auto replies can make threads unreadable later. Two tips:

  1. Keep the subject of your auto reply generic:

    • “Out of Office” is enough.
    • Avoid including the original subject in your template when using rules; Outlook usually handles threading but replies to replies can start nesting badly.

  2. In your body, clearly separate your message from theirs:

    • Put a clear line like:
      ----
Original message follows:
    • This helps when someone forwards your auto reply plus the original to another person.

4. Handling VIPs differently without overbuilding rules

You do not actually need complex rules for everything.

Simple pattern that works well:

  • Turn on Automatic Replies for everyone.
  • Add one rule for VIPs:
    • Condition: from specific people or domains.
    • Actions:
      • Mark as high importance.
      • Move a copy to a “VIP while out” folder.
      • Optionally forward to your backup.

You do not have to create a separate auto reply template for VIPs unless you really need special wording. In most cases, the same message is fine, the handling behind the scenes is what changes.

5. When rules-based replies are actually better

If you are on POP/IMAP and forced to use the rule + template trick, you are stuck with Outlook having to stay open. That is a con. One pro, though: rules can be incredibly granular.

Useful cases:

  • Different templates for different languages:

    • Condition: sender domain, or address book category.
    • Action: “reply using a specific template” with a localized message.

  • Only reply to new conversations:

    • Use a condition like “where my name is in the To box” and an exception for messages marked as “replied” or certain subjects to cut down on noisy loops.

This is more work to maintain but more flexible than the standard automatic reply dialog.

6. Think about calendar + auto reply together

Outlook lets you put your absence in multiple places:

  • Your calendar: set yourself as “Out of Office” during the period.
  • Automatic Replies: the mail side.

To avoid confusion:

  • Make the calendar event title match your email wording:
    • If your auto reply says “I will not be checking email,” your calendar should probably say “OOO, no email access,” not “Working remotely.”
  • If you know the exact return time, put it in both places, for example:
    • Auto reply: “I will respond after 16 Feb, 10:00.”
    • Calendar: event until 16 Feb, 10:00.

Consistency helps your coworkers read your status correctly.

7. About that empty product title “”

There is no literal product here, but think of your “Outlook automatic reply setup” as a product you are shipping to everyone who emails you.

Pros of this “product”:

  • Clear expectations
  • Fewer “just checking in” nudges
  • Professional impression if well written

Cons:

  • Potential privacy / security leak if you overshare travel info
  • Can cause automation loops if paired with other auto systems
  • Can clutter people’s inboxes if too verbose or always on

Competitors here are basically the two approaches already laid out by @shizuka (very clear click-path how-to) and @byteguru (decision guide for which feature to use). Combining their instructions with the testing, risk tuning, and calendar alignment above gives you a setup that is not just working, but actually practical.

If you paste which Outlook you have (for example: “Outlook for Microsoft 365 desktop with work account” or “Outlook with Gmail via IMAP”), I can suggest one concise internal text and one external text tailored to your situation so you can drop them straight into the Automatic Replies box without overthinking.