You may notice that Outlook no longer displays warnings before you send an email. This happens when the Mail Tips feature is turned off or not configured correctly. Mail Tips provide alerts about issues like missing attachments or sending to a large group. This article explains how to re-enable these warnings in the new Outlook.
Key Takeaways: Enabling Mail Tips in New Outlook
- Settings > Mail > Compose and reply: The primary location to turn on Mail Tips for missing attachments and large audiences.
- File > Options > Mail > MailTips: Opens the classic dialog box for advanced Mail Tips configuration in the new Outlook.
- MailTips Options button: Controls specific warning types like recipient out of office or restricted permissions.
Why Mail Tips Are Essential for Safe Sending
Mail Tips are proactive alerts that appear in the message composition window. They warn you about potential problems before you click Send. Common warnings include forgetting an attachment you mentioned, sending to a very large distribution list, or emailing someone who is out of the office.
In the new Outlook, these tips are managed through a simplified settings menu. However, some advanced controls still require the classic Outlook Options dialog. The feature may be disabled if your organization’s IT policies restrict it or if it was manually turned off.
Prerequisites for Mail Tips to Work
Your account must be connected to a Microsoft Exchange Server or Microsoft 365 for most Mail Tips to function. Some basic tips, like the attachment reminder, work with other account types like Outlook.com or IMAP. You also need to be using the new Outlook for Windows, as the steps differ from the classic desktop app.
Steps to Turn On Mail Tips in New Outlook
Follow these steps to enable the core sending warnings. Start from the main Outlook window.
- Open Settings
Click the gear icon in the top-right corner of the new Outlook window to open the Settings pane. - Navigate to Mail settings
In the Settings pane, select the Mail category from the list on the left side. - Select Compose and reply
Scroll down within the Mail settings and click on Compose and reply. - Enable the key warnings
On the right, find the section for Mail Tips. Turn on the switches for Show warnings for missing attachments and Show warnings for large audiences.
Accessing Advanced Mail Tips Options
For more granular control, use the classic options dialog. This is required for tips about external recipients or mailbox full status.
- Open File menu
In the new Outlook, click File on the ribbon. If you don’t see File, ensure you are not in the simplified ribbon view. - Go to Options
In the File menu, select Options at the bottom of the left-hand pane. This opens the Outlook Options window. - Select the Mail tab
In the Outlook Options window, click on Mail in the left sidebar. - Click the MailTips button
Scroll down to the MailTips section and click the MailTips Options button. A new dialog box will appear. - Select your warnings
In the MailTips Options dialog, check the boxes for each specific warning you want to see, such as Automatic replies or Recipient’s mailbox full. Click OK twice to save.
If Mail Tips Still Do Not Appear
Mail Tips Are Grayed Out or Unavailable
If the settings are inactive, your Microsoft 365 or Exchange administrator has likely disabled the feature organization-wide. You must contact your IT support team to request it be enabled. This is common with strict compliance or security policies.
Only Some Tips Work for Certain Recipients
Mail Tips for external recipients or out-of-office status require the recipient to also be on a compatible Exchange system. If they use a different email service like Gmail, those specific tips will not generate. The attachment reminder is local and should always work if enabled.
New Outlook Shows Different Interface
Microsoft frequently updates the new Outlook. If the steps above do not match your interface, use the search bar in Settings. Type Mail Tips to find the current location of the toggle switches quickly.
Mail Tips Settings: New Interface vs Classic Dialog
| Item | New Outlook Settings | Classic MailTips Options |
|---|---|---|
| Access Path | Settings > Mail > Compose and reply | File > Options > Mail > MailTips Options |
| Primary Controls | Simple on/off toggles for common warnings | Detailed checkbox list for all tip types |
| Attachment Reminder | Controlled directly in the main settings pane | Configured in a separate dialog (Editor Options) |
| Administrator Policies | May hide the entire section if disabled | Options may be visible but unchangeable |
| Best For | Quickly enabling basic send warnings | Precise control in an Exchange environment |
You can now send emails with confidence, knowing Outlook will warn you of common mistakes. Check the Mail Tips settings after any major Outlook update, as toggles can sometimes reset. For more control, use the classic MailTips Options dialog to fine-tune alerts for your specific workflow.