How to Fix Outlook SMTP Authentication and STARTTLS Errors in Windows Live Mail
Question details
Users are unable to send emails via an Outlook account using Windows Live Mail due to SMTP authentication or STARTTLS errors, despite receiving emails normally.
- Product
- Windows Live Mail / Microsoft Outlook
- Device & OS
- Windows 7 Professional
- Scenario
- Attempting to send outgoing messages from a laptop using Windows Live Mail configured with an Outlook account.
- Observed behavior
- Incoming emails are received successfully, but outgoing emails fail to send due to SMTP authentication and STARTTLS encryption errors.
Ensure you are logged into your Windows 7 computer as an administrator, as you will need to modify system internet properties and verify your email account security settings.
Enable TLS 1.2 on Windows 7
Modern email servers require TLS 1.2 for secure connections. Enabling this protocol in Windows 7 often resolves STARTTLS errors.
Windows Live Mail relies on the underlying Windows operating system for its security protocols. Since TLS 1.2 is not enabled by default on all Windows 7 machines, you must manually activate it to allow secure SMTP connections and clear the STARTTLS error.
Click the Windows Start menu, type "Internet Options" into the search box, and press Enter to open the Internet Properties dialog.
Click on the "Advanced" tab located at the top right of the Internet Properties window.
Scroll down the Settings list to the "Security" section. Check the boxes next to "Use TLS 1.1" and "Use TLS 1.2".
Click "Apply" and then "OK". Restart your computer to ensure the new security protocols are applied to Windows Live Mail.
Generate an App Password for Outlook
Legacy clients like Windows Live Mail do not support modern OAuth2 authentication, requiring a specific App Password to bypass SMTP errors.
Migrate to a Modern Email Client
If Windows Live Mail still fails to authenticate, migrating to a modern, supported email client is necessary for continued secure access.
Discover WPS Office for Your Daily Productivity Needs
If you are dealing with legacy Microsoft software issues like Windows Live Mail errors, it might be time to modernize your digital workspace. WPS Office is a fast, lightweight, and highly compatible alternative to Microsoft Office that meets all your document creation needs without the hassle.
- 1. Download the Installer: Visit the official WPS Office website and click the Free Download button.
- 2. Install WPS Office: Run the downloaded executable file and follow the on-screen prompts to install the suite on your Windows PC.
- 3. Start Creating: Open WPS Writer, Spreadsheet, or Presentation to immediately start working on your documents.
Frequently Asked Questions
Why do outgoing emails fail while incoming emails work in Windows Live Mail?
Incoming emails (POP3/IMAP) and outgoing emails (SMTP) use different servers and security requirements. Your outgoing server likely demands stricter modern encryption, such as TLS 1.2, which your client currently fails to provide.
Why does the exact same email account work on my Windows 7 desktop but not my laptop?
Your desktop computer likely received a specific Windows Update that enabled TLS 1.2 or modern cipher suites by default, whereas the laptops are missing that specific security patch.
What does the STARTTLS error mean in email clients?
A STARTTLS error indicates that your email client is trying to upgrade an insecure connection to a secure one using encryption, but the server and client cannot agree on a supported security protocol.
Is it safe to continue using Windows Live Mail on Windows 7?
No, it is highly discouraged. Both Windows 7 and Windows Live Mail have reached their end-of-support dates. They no longer receive security updates, leaving your email data vulnerable and increasingly incompatible with major modern email providers.
