My Outlook Automatic replace function is not working

Question

I have tried repeatedly to create an automatic reply using the Outlook option - File/Account /Automatic replies , but unfortunately without success. How can I activate the feature?

Answer 1

Hi @Zlatina Bozhkova, 

Thank you for reaching out to the Microsoft Q&A forum and for clearly outlining your concern. 

Based on the details you shared that Automatic Replies in Classic Outlook do not activate when you select File, Account, Automatic Replies. I truly understand and appreciate your effort in testing experiences and reaching out.  Automatic Replies run on the server for Exchange and Microsoft 365 mailboxes and the system sends one reply per sender during your away period. In contrast, POP and IMAP accounts do not support server based Automatic Replies in Classic Outlook and therefore require a rule based workaround inside Outlook. Furthermore, organization controls such as remote domain settings, mail flow rules, or the EWS path can suppress or block replies to external senders. 

To address this, please follow the steps below that suit for your situation: 

1/ For Exchange or Microsoft 365 accounts, enable Automatic Replies in both Classic Outlook and on the web 

• In Classic Outlook, go to File > Automatic Replies, choose Send automatic replies, optionally set a Start/End time, add your Inside My Organization and Outside My Organization messages, then OK.  
• Also enable it on the server to rule out a client dialog issue: open Outlook on the web > Settings (gear) > Mail > Automatic replies, turn it On, set the time range and external reply as needed, then Save.  
• Test with two senders: one inside your org and one external. By design, each sender should get a single reply during your OOF period.  
• Reference: How to set up out of office automatic replies in Outlook - Microsoft Support 

2/ For POP or IMAP accounts, create an automatic reply using a template and a rule in Classic Outlook 

(This works while Outlook stays running on your PC.) 

• Create your message template: New Email > write your away note > File > Save As > Outlook Template (*.oft).  
• Create the rule: File > Manage Rules & Alerts > New Rule > Apply rule on messages I receive > Next (apply to all) > confirm Yes > select reply using a specific template > User Templates in File System > pick your .oft > Next > add exceptions if needed > Finish.  
• Leave Outlook open while you’re away so replies are sent automatically.  
• Reference: Use rules to create an out of office message in Outlook - Microsoft Support 

3/ If replies work internally but not externally, ask your administrator to validate organization settings 

• First, in Exchange Admin Center review Mail flow and Remote domains to ensure automatic replies are allowed for the relevant domains and that the AllowedOOFType permits external replies.  
• Next, check mail flow rules so that automatic replies with a blank return path are not blocked and adjust the match to header or envelope where needed.  
• Finally, confirm that the mailbox can set Automatic Replies through EWS and, if required, toggle the setting using the mailbox auto reply configuration at the admin level.  
• Reference: Understand and troubleshoot Out of Office (OOF) replies - Exchange | Microsoft Learn 

If you follow the steps above and the issue still persists, kindly attach a screenshot of the behavior to help with a quicker diagnosis. Additionally, please confirm the account type listed under File > Account Settings > Account Settings (Exchange, Microsoft 365, POP, or IMAP) so I can tailor the next steps precisely to your setup.  

I hope this response has helped address your question and clarify the behavior you're experiencing. Please feel free to reply if you have any further questions, I would be happy to assist further.   

Thank you for your patience and your understanding. I look forward to continuing the conversation.   

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Answer 2

To activate and use automatic replies in Classic Outlook for Windows, first confirm that the account type supports the built‑in Automatic Replies feature, then configure it as follows.

1. Check the account type
   1. In Outlook, select File > Account Settings > Account Settings.
   2. On the E‑mail tab, look at the Type column for the account:
      • If it shows Microsoft Exchange or Microsoft 365/Exchange Online, the built‑in Automatic Replies feature should work.
      • If it shows POP3 or IMAP, the Automatic Replies button either will not appear or will not function for server‑side auto‑replies. In that case, a rule must be used instead (see step 3).
2. Turn on Automatic Replies (Exchange / Microsoft 365 accounts)
   1. Select File > Automatic Replies.
   2. In the Automatic Replies dialog, select Send automatic replies.
   3. (Optional) Select Only send during this time range, then choose Start time and End time.
   4. On the Inside My Organization tab, type the message that should be sent to colleagues.
   5. To send replies outside the organization, go to the Outside My Organization tab (or Send automatic reply messages to External Senders in Outlook Web App Light), enable external replies, and enter the external message.
   6. Select OK to activate the feature.
   Notes:
   • If Automatic Replies is visible but appears not to work, verify that a message is actually entered in the reply text box; if it is left blank, no reply is sent.
   • Ensure Don’t send automatic replies is not selected.
3. If the account is POP3/IMAP: emulate Out of Office using a rule If the account type is POP3 or IMAP, use a rule to send automatic replies while Outlook is running:
   1. Create a reply template (message body for the auto‑reply) as described in the “Define an automatic reply template” section of Emulate the Out of Office Assistant in Outlook.
   2. Select File > Manage Rules & Alerts.
   3. On the E‑mail Rules tab, select New Rule.
   4. Under Start from a blank rule, choose Apply rule on messages I receive, then select Next.
   5. Under Which condition(s) do you want to check, select sent only to me or any other conditions needed, then select Next.
   6. Under What do you want to do with the message, select reply using a specific template.
   7. In Step 2: Edit the rule description, select the underlined a specific template text.
   8. In Select a Reply Template, choose the reply template created earlier and select Open.
   9. Complete the wizard, select Finish, then OK.
   Important behavior:
   • This rule sends the reply only once per sender per Outlook session to avoid repeated replies.
   • Outlook must remain running for these rule‑based replies to be sent.
4. If Automatic Replies fails only for a shared mailbox If trying to open Automatic Replies for a shared mailbox and seeing “Your automatic reply settings cannot be displayed because the server is currently unavailable,” set automatic replies for that shared mailbox using Outlook on the web (OWA) instead, as described in Cannot open the Automatic Replies setting of a shared mailbox in Classic Outlook.

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References:

• Set up auto-reply (out of office)
• Create signatures and automatic replies in Outlook for Windows
• How to use the Out of Office or Automatic Reply in Outlook on Windows 10
• Emulate the Out of Office Assistant in Outlook
• Options > Automatic Replies
• Cannot open the Automatic Replies setting of a shared mailbox in Classic Outlook