Automatic replies in Outlook 365, also known as Out of Office (OOO) messages, are a crucial feature for maintaining communication while you are away. However, sometimes these automatic replies may not function as expected. This could happen due to various reasons like automatic reliable not work when MS Outlook is closed or if the server is not stable.
If you find yourself in this situation, don’t worry. This blog post will guide you through common reasons why automatic replies might not be working and provide solutions to fix the issue.

Why Automatic Replies Do Not Work? Causes and Fixes
1. Incorrect Configuration
One of the most common reasons for automatic replies not working is incorrect configuration.
Steps to Check:
- Open Outlook.
- Go to File > Automatic Replies (Out of Office).
- Ensure that automatic replies are selected.
- Set the start and end times correctly.
- Check the message content for both internal and external contacts.
Solution:
Verify that you have enabled automatic replies for the correct date range and that the message is properly set up for both internal and external recipients.
2. Rules Interference
Sometimes, rules in MS Outlook can interfere with automatic replies. Here is how you can check the rules being created in MS Outlook to ensure that it is not interfering with the automatic reply
Steps to Check:
- Open Outlook.
- Go to File > Manage Rules & Alerts.
- Check for any rules that might move or delete incoming messages.
Solution:
Ensure that not create rules in MS Outlook to move or delete incoming emails that could prevent the automatic reply from being sent.
3. Server-Side Issues
For those using Exchange Server, server-side issues can prevent automatic replies from working.
Steps to Check:
- Check Server Status:
- Ensure your Exchange server is running and there are no connectivity issues.
- Outlook Web App (OWA):
- Log in to your Outlook Web App and try setting up the automatic replies there. If it works on OWA but not on the desktop client, the issue might be with your Outlook client configuration.
Solution:
Contact your IT department or Exchange administrator to verify that the server is functioning correctly and that there are no ongoing issues.
4. Cached Mode Issues
Outlook running in cached mode can sometimes cause issues with automatic replies.
Steps to Check:
- Open Outlook.
- Go to File > Account Settings > Account Settings.
- Select your account and click Change.
- Uncheck the Use Cached Exchange Mode box.
Solution:
Turn off cached mode and restart Outlook to see if the automatic replies start working. If they do, there might be an issue with the local cache.
5. Outdated Outlook Version
An outdated version of Outlook can sometimes cause features to malfunction.
Steps to Check:
- Open Outlook.
- Go to File > Office Account.
- Click on Update Options > Update Now.
Solution:
Ensure that your Outlook is up to date with the latest patches and updates from Microsoft.
6. Mailbox Quota Issues
If your mailbox is full, it might prevent automatic replies from being sent.
Steps to Check:
- Open Outlook.
- Check your mailbox size: Go to File > Tools > Mailbox Cleanup.
Solution:
Clear out unnecessary emails or archive old messages to free up space in your mailbox. You can also compact the OST file if the size is still large.
7. External Email Server Issues
Sometimes, the issue might be on the recipient’s email server.
Steps to Check:
- Test with Different Email Accounts:
- Send test emails to different email accounts (internal and external) to check if the problem is specific to certain domains.
Solution:
If the issue persists only with specific external email accounts, the problem might be with the recipient’s email server settings.
Conclusion
Automatic replies in Outlook 365 are a vital feature for ensuring smooth communication during absences. If your automatic replies are not working, it could be due to incorrect configuration, interference from rules, server-side issues, cached mode problems, outdated software, mailbox quota limitations, or external email server issues. By systematically checking and addressing each potential issue, you can resolve most problems and ensure that your automatic replies function correctly.