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Quick Answer

Open File > Automatic Replies, confirm Send automatic replies is selected and the date range covers today, then open the Outside My Organization tab and choose Anyone outside my organization.

How to Fix Out-of-Office Replies Not Sending ​

Applies to: Microsoft 365 and Exchange mailboxes (classic Outlook desktop, new Outlook, Outlook on the web)
Article Type: Troubleshooting
Last Updated: 2026-07-29

Summary ​

You set an out-of-office reply, went away, and came back to a pile of people saying they never heard anything. This article walks the six things that actually break automatic replies, in the order worth checking, and gives you the exact wording to send IT for the two causes you cannot fix yourself.

Symptoms ​

  • Automatic replies show as switched on in Outlook, but senders report they received nothing.
  • Colleagues inside the company get your reply and clients outside it do not.
  • The reply went out on the first day of your leave and then stopped.
  • You emailed yourself twice from a personal account and only the first message triggered a reply.
  • Mail arriving at a shared mailbox you monitor gets no acknowledgement, even though your own out-of-office is on.
  • The Automatic Replies option is missing from the File menu entirely.

Prerequisites ​

  • A Microsoft 365 or Exchange mailbox. POP and IMAP accounts have no server-side automatic replies at all.
  • Access to Outlook in any form — classic desktop, new Outlook, or Outlook on the web.
  • For the shared mailbox steps, Full Access permission on that mailbox.

Instructions ​

1. Confirm Automatic Replies Are Actually Turned On ​

Start here even when you are certain. A dialog closed with the X instead of OK saves nothing.

Classic Outlook:

  1. Click File on the ribbon. The Account Information page opens.
  2. Click Automatic Replies (Out of Office). The Automatic Replies dialog opens.
  3. Check which radio button at the top is filled: Do not send automatic replies or Send automatic replies. Select Send automatic replies if it is not already.
  4. Click OK at the bottom of the dialog — not the X in the corner.
  5. Look at the top of your message list. A yellow banner reading Automatic Replies are being sent for this account confirms the setting took.

New Outlook and Outlook on the web:

  1. Click the Settings gear icon in the top-right corner, then select Mail > Automatic replies.
  2. Confirm the Automatic replies on toggle is blue and pushed to the right.
  3. Click Save. Recent builds save as you type and show no button.

Verification: Close the dialog completely, reopen it, and read the toggle again. A setting that reverts on reopen means the save did not reach the server — check your connection status in the bottom-right corner of the Outlook window and try again once it reads Connected.

2. Check the Date Range ​

This is the single most common cause. The feature is on, the message is written, and the clock has already run out.

  1. In the Automatic Replies dialog, look at the Only send during this time range checkbox.
  2. If it is ticked, read the Start time and End time underneath it. Both a date and a time sit on each line.
  3. Confirm today's date and the current time fall between the two. An end time of 9:00 AM today means replies stopped this morning.
  4. Correct the dates, or untick Only send during this time range to run the reply until you switch it off manually.
  5. Click OK.

In new Outlook and on the web, the same control reads Send replies only during a time period, with Start time and End time fields below it.

Note: The times run on your mailbox's time zone, not your laptop's. If you set the range while travelling, an end time can land hours earlier than you intended. Check the time zone under File > Options > Calendar in classic Outlook, or Settings > General > Language and time in new Outlook.

3. Turn On External Replies and Widen the Audience ​

Internal and external replies are two separate messages behind two separate switches. Turning the feature on only arms the internal one.

Classic Outlook:

  1. In the Automatic Replies dialog, click the Outside My Organization tab. The tab label reads Outside My Organization (On) or (Off), which tells you the answer before you click.
  2. Tick Auto-reply to people outside my organization at the top of the tab.
  3. Choose between the two radio buttons directly beneath it:
    • My Contacts only — replies only to senders saved in your Outlook Contacts folder. Every customer, supplier, and stranger gets silence. This is the setting that quietly drops most of your senders.
    • Anyone outside my organization — replies to every external sender. Select this one unless you have a deliberate reason not to.
  4. Type your external message in the large text box. An empty box sends nothing even with the switch on.
  5. Click OK.

New Outlook and Outlook on the web:

  1. Go to Settings > Mail > Automatic replies.
  2. Tick Send replies outside your organization below the internal message box.
  3. Leave Send replies only to contacts unticked. Ticking it is the same trap as My Contacts only above.
  4. Type the external message in the second text box, then click Save.

Note: Your internal message does not copy across to the external tab. Two boxes, two messages — write both.

4. Test It Correctly, Because Outlook Replies Once Per Sender ​

Exchange sends one automatic reply per sender for the whole out-of-office period. Testing this wrong makes a working setup look broken.

  1. Send a test message to your work address from an outside account you have not already used for a test.
  2. Wait up to two minutes. Automatic replies are queued by the server, not sent instantly by Outlook.
  3. Check the Junk Email folder of the test account as well as its inbox.
  4. To retest from an address you already used, reset the sender list first: open the Automatic Replies dialog, select Do not send automatic replies, click OK, then turn it back on. The list of who has already been replied to clears.

Note: This once-per-sender behaviour is deliberate — it stops two automatic replies bouncing off each other forever. It also means a colleague who emailed you on day one hears nothing for the rest of the fortnight, which is normal and not a fault.

5. Look for a Rule Competing with the Server Setting ​

Automatic replies and inbox rules run in the same pipeline, and a rule can shut the reply down before it fires.

  1. In the Automatic Replies dialog, click Rules at the bottom-left of the Inside My Organization tab. The Automatic Reply Rules dialog opens.
  2. Read the list. Any rule here runs against incoming mail while automatic replies are on. Delete or untick anything you did not deliberately create — a rule that moves or deletes mail on arrival can take the message out of scope before the reply is generated.
  3. Close that dialog, then click File > Manage Rules & Alerts and look through Email Rules for two patterns:
    • A rule using have server reply using a specific message — a second, competing auto-responder that keeps running whether or not your out-of-office is on.
    • A rule using reply using a specific template — this one is client-side. It only fires while Outlook is open on your computer, so it goes silent the moment you close your laptop and leave.
  4. Untick the box beside any rule you want to stand down, then click OK.
  5. Look for stop processing more rules in the description pane of any rule sitting above the others. It ends rule processing for that message.

Rules that misbehave in other ways are covered in How to Fix Outlook Rules Not Working or Running Automatically, and the mechanics of building one are in How to Create Email Rules in Outlook.

6. Set the Reply on a Shared Mailbox, Not on Your Own Account ​

An out-of-office on your personal mailbox has no effect on mail addressed to a shared mailbox, even one you monitor all day.

  1. Click your profile picture in the top-right corner of Outlook on the web, then select Open another mailbox.
  2. Type the shared mailbox address, select it from the list, and click Open. The mailbox opens in a new browser tab under its own name.
  3. In that tab, click the Settings gear icon, then Mail > Automatic replies.
  4. Turn Automatic replies on, set the time period and both messages, then click Save.
  5. Confirm the browser tab still shows the shared mailbox name and not your own before you close it.

If Open another mailbox returns an error, you lack the permission. Tell IT: "Please grant me Full Access to the shared mailbox [email protected] so I can set its automatic replies." If you would rather they set it directly, send: "Please turn on automatic replies for the shared mailbox [email protected] from 3 August to 10 August, with this message for internal and external senders," followed by the text you want sent.

Setting up an autoresponder on a shared address from scratch is covered in How to Set Up an Email Autoresponder for a Shared Mailbox.

7. Rule Out a Blocked Policy or a Recipient Spam Filter ​

Two causes sit outside your mailbox. Both are identifiable from your desk.

  1. Check whether the feature exists at all. If Automatic Replies (Out of Office) is missing from the File menu, or Automatic replies is missing from Settings > Mail, the account is either POP/IMAP or the feature is switched off by policy.
  2. Confirm the account type: File > Account Settings > Account Settings, then read the Type column beside your address. Anything other than Microsoft Exchange or Microsoft 365 has no server-side automatic replies.
  3. If it is an Exchange account and the option is missing or greyed out, the block is organisational. Tell IT: "Automatic replies are unavailable on my mailbox. Please confirm the OWA mailbox policy or role assignment is not blocking them, and enable automatic replies for my account."
  4. If internal replies arrive and external ones never do — even with Step 3 configured correctly — the block sits on the outbound domain settings. Tell IT: "External automatic replies are not leaving the organisation. Please check the remote domain configuration and set AllowedOOFType to External for our default remote domain."
  5. If a single recipient reports nothing while others receive replies, ask them to check their Junk Email or Spam folder. Automatic replies carry an empty return address by design, and some filters treat that as a spam signal.

Verification: A successful external test lands in the outside account's inbox or junk folder within two minutes and carries your external message text, not your internal one. Getting the internal text externally means the Outside My Organization message box is empty and Exchange fell back.

Troubleshooting ​

INFO

Exchange tracks who has already received your automatic reply and sends each person one message per out-of-office period. Turning automatic replies off and on again clears that list. Every "it only worked once" report traces back to this behaviour rather than a fault.

Symptom / ErrorPotential CauseSolution
Internal colleagues get the reply, external senders do notExternal replies switched offTick Auto-reply to people outside my organization on the Outside My Organization tab (Step 3).
Only a handful of external people received itMy Contacts only is selectedSwitch to Anyone outside my organization (Step 3). The contacts-only option excludes anyone not in your Contacts folder.
Replies stopped partway through your leaveDate range expiredReopen the dialog and extend the End time, or untick Only send during this time range (Step 2).
Your second test email got no replyOne reply per sender, by designTest from a different outside address, or toggle automatic replies off and on to reset the list (Step 4).
Automatic Replies is missing from the File menuPOP/IMAP account or a policy blockConfirm the account type under File > Account Settings (Step 7), then send IT the wording in that step.
Mail to the shared mailbox gets no replyReply set on your own accountOpen the shared mailbox directly and set the reply there (Step 6).
The reply text is the internal one going to outside sendersExternal message box left emptyType a separate message in the Outside My Organization box and click OK (Step 3).