How to Fix Outlook Not Sending Emails on Mac

Edited 2 weeks ago by ExtremeHow Editorial Team

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Microsoft Outlook is a widely used email client that provides users with robust email management features. However, sometimes you may face a problem where Outlook is not sending emails on your Mac. This comprehensive guide will help you understand the possible reasons behind Outlook not sending emails and provide you with step-by-step solutions to resolve this issue efficiently.

Understanding the problem

Before learning the solutions, it's important to understand why Outlook is not sending emails on Mac. This understanding can help you troubleshoot and fix the problem more effectively. Common causes include:

• Network connectivity issues: A common cause is unstable or disconnected Internet on your Mac.
• Incorrect email settings: This could include incorrect SMTP server configuration or incorrect port numbers.
• Older version of Outlook: Running an older version of Outlook can cause compatibility issues with MacOS.
• Large email attachments: Emails with large attachments can get stuck in the outbox.
• Conflict with antivirus software: Sometimes security software can interfere with Outlook's email sending function.
• Account authentication issues: Problems with account credentials or two-step verification may prevent email sending.

Step-by-step solution

Check your internet connection

The first and most important step is to make sure your Mac is properly connected to the Internet. Here’s how you can verify:

1. Open a web browser like Safari or Chrome on your Mac and try opening a website.
2. If the website loads, your connection is fine. If not, try the following:
• Reset your Wi-Fi connection by turning it off and then on again.
• Restart your router and check any connectivity settings on your Mac.
• If you're using a VPN, disable it temporarily so it doesn't affect your ability to send email.

Verify and update email account settings

A common problem with Outlook not sending emails is incorrect account settings, specifically SMTP settings. Here's how you can check and update them:

1. Open Outlook on your Mac and go to Preferences.
2. Under Account, select the account that isn’t sending email.
3. Check the outgoing server (SMTP) settings. Make sure that:
• The SMTP server name is correct.
• The correct encryption type is selected (usually SSL or TLS).
• The port number is set correctly (usually 465, 587).
4. Make sure the username and password for the server are entered correctly and update it if necessary.
5. Test by sending an email to verify if the settings are working.

Update Outlook application

If you're using an older version of Outlook, updating the app may resolve known bugs and improve functionality:

1. Open the App Store on your Mac.
2. Go to the Updates section.
3. If an update is available for Outlook, click Update to install the latest version.

After updating, restart Outlook and check if you can send emails.

Reduce email attachment size

Large attachments can cause your emails to get stuck. As a solution, consider compressing files or using a cloud sharing service like OneDrive or Google Drive:

Upload your file to Google Drive

    Upload your file to OneDrive

Once uploaded, create a shareable link and include it in your email as an attachment.

Check for conflicts with antivirus software

Sometimes antivirus programs can scan outgoing emails and block them. Check your antivirus settings:

1. Open the antivirus application installed on your Mac.
2. Look for any settings related to email security or scanning.
3. Temporarily disable email scanning or add Outlook as an exception to see if that resolves the issue.
4. Keep in mind that this step should be taken with caution as disabling email scanning can expose you to security risks. Make sure you enable it back once the test is complete.

Troubleshoot account authentication issues

Account authentication issues can sometimes prevent emails from sending. Make sure your login credentials are correct and check if you need to adjust any two-factor authentication settings:

1. Go to the webmail version of your email provider to make sure your credentials are correct.
2. If your account uses two-factor authentication, generate an app-specific password for Outlook.
• For example, if you're using an Apple ID with two-factor authentication, go to Apple ID Management and log in.
• Find the App-specific passwords section and click Generate password…
• Use this password in Outlook for the affected account.

Check Outlook Outbox

Emails stuck in the Outbox can prevent further email sending:

1. Open your Outbox in Outlook.
2. Check if there are any emails in the queue. If yes, try sending them again or delete them from the outbox.
3. If an email is large or time-sensitive, shorten the subject line or attachment and try sending again.

Reset the SMTP server

If email setup problems persist, try resetting your SMTP server:

1. In Outlook, go to Preferences and choose Accounts.
2. Select the account that is having problems and under the SMTP Server list, change to another server if one is available.
3. If you only have one server, delete it and re-add it manually with the correct settings.

Test from safe mode

If the problem persists, run Outlook in safe mode. This disables add-ins and other customizations that may affect email sending:

1. Close Outlook if it is open.
2. Hold down the Option key and open Outlook. You will see a prompt giving you the option to start in Safe Mode.
3. Test sending email in safe mode.

Re-add the account

As a last resort, try removing your email account from Outlook and then re-adding it:

1. In Outlook, go to Preferences > Accounts.
2. Select the problematic account and use the - button to delete it.
3. Re-add the account using the + and enter your email credentials.
4. Ensure your settings and test if you can send emails.

Conclusion

By following these troubleshooting steps, you should be able to resolve the issue of Outlook not sending emails on your Mac. If the problem persists after all the solutions provided, consider contacting your email provider for assistance. They may have specific settings or additional security steps you need to configure. Persistence and systematic troubleshooting are key to resolving email problems, and going through each step can uncover hidden settings or conflicts that are otherwise easy to overlook.

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