why do my automatic replies on outlook keep turning itself off every time I close and reopen the application??

Hi @Shaver Dana, 

I hope you are having a wonderful day today. I wanted to confirm that your Automatic Replies in Outlook Web are turning off each time you close and reopen the application. 

This typically occurs because Automatic Replies in Outlook Web are sometimes stored as a local session preference rather than being fully saved to the server. As a result, when the browser session ends or the application is refreshed, the setting may not persist as expected. Furthermore, a very common reason this happens is accidentally clicking the "Turn Off" link on the notification banner that appears each time you open Outlook, as the dismiss button and the "Turn Off" link are placed very close together, making it easy to disable without noticing. If the feature is set with a time period, it can automatically stop once the configured end time passes, and if the mailbox is POP or IMAP, server based automatic replies are not supported, which can also lead to unexpected behavior. 

To help you get this working correctly, please kindly follow the steps below: 

1/ Set automatic replies directly via Outlook web settings

• Open your browser and go to outlook.office.com 
• Click the Gear icon (⚙️) in the top-right corner. 
• In the search bar, type "Automatic Replies" and select it. 
• Toggle Automatic Replies ON, enter your message, then click Save. 
• Setting it this way saves the preference directly to Microsoft's servers, so it will stay active regardless of whether your browser is open or closed. 
• Reference: Send automatic out of office replies from Outlook.com or Outlook on the web - Microsoft Support 

2/ Be mindful of the "Turn Off" banner when opening Outlook 

• Each time you open Outlook Web, a notification banner appears at the top reminding you that Automatic Replies are active. 
• The "X" (close) button and the "Turn off" hyperlink are placed very close together. 
• When dismissing this banner, please click only the "X" on the far right, do not click the "Turn off" text next to it. 
• This small step alone may be the key reason your replies keep getting disabled. 
• Reference: Options > Automatic Replies - Microsoft Support 

3/ Verify the mailbox type supports server based automatic replies 

• If you have access to Outlook for Windows, open Outlook, select File, select Account Settings, then select Account Settings, and check the Type column for the mailbox. 
• If the mailbox type is Microsoft Exchange or Microsoft 365, automatic replies should work as a mailbox setting. 
• If the mailbox type is POP or IMAP, use a rule based reply method instead because automatic replies are not supported for those mailbox types. 

4/ Isolate whether the browser session is preventing the setting from persisting 

• After saving the setting, sign out of Outlook on the web, sign back in, and then check Automatic replies again to confirm it remains enabled. 
• As an additional isolation step, try the same change in a private browsing session and then recheck the Automatic replies page after you select Save. 
• If it stays enabled in private browsing, temporarily disable browser extensions in your normal session and test again, because extensions can affect how settings pages load and save.  

5/ Use a server-side rule as a backup 

• If the issue continues, you can create a server-side rule that automatically replies to incoming emails. 
• In Outlook Web, click the Gear icon > View all Outlook settings > Mail > Rules > Add new rule. 
• Set the condition to "Apply to all messages" and the action to "Reply". 
• Type your auto-reply message and click Save. 
• Reference: Manage email messages by using rules in Outlook - Microsoft Support 

This rule runs directly from the server, so it will remain active at all times without being affected by your browser or session status 

I truly appreciate your patience throughout this matter and hope that the steps above are helpful to you. Should you have any further questions or require additional assistance, please do not hesitate to get back to me and I will be more than glad to help. 

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

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Automatic replies in Outlook on the web turn off or appear not to work if they are not fully configured or saved for both internal and (optionally) external senders.

Check these points when setting them up:

1. Turn on automatic replies
   • Go to Options > Automatic Replies.
   • Select Send automatic replies (not Don’t send automatic replies).
2. Make sure a message is entered
   • In Send a reply once to each sender inside my organization with the following message, type the message.
   • If no message is entered, no automatic reply is sent even if the feature is turned on.
3. If using a time period, verify dates
   • If Send replies only during this time period is selected, check that the Start time and End time are correct and that the end time is not already in the past. When the end time is reached, automatic replies stop.
4. Check external sender settings (if needed)
   • If replies should go to people outside the organization, select Send automatic reply messages to External Senders and enter a message.
   • Choose either Send replies only to senders in my Contacts list or Send replies to anyone outside my organization as required.
5. Replace existing messages if necessary
   • If there is an older auto-reply stored, select Replace my current automatic reply message with the following (for internal and/or external) so the new text is actually used.

If any of these settings are missing or the time window has expired, Outlook will behave as if automatic replies are off the next time it is opened.

References:

• Options > Automatic Replies
• Out of Office replies for an On-premises Exchange mailbox are not working when enabled from Outlook Mobile