Fixing MS Outlook Proxy Server Security Certificate Issues

2023/11/28

Key Notes

Enable TLS 1.0 and 1.2 for secure connections.
Run AutoDiscover to verify server settings.
Utilize TCP/IP protocol for Microsoft Exchange accounts.

Resolving Outlook Email Issues After Upgrading to Windows 11

Experiencing email reception problems in Microsoft Outlook after migrating to Windows 11? This guide provides essential steps to troubleshoot proxy server certificate errors and restore functionality.

Step-by-Step Solutions to Fix Outlook Email Problems

Step 1: Enable TLS 1.0 in the Registry Editor

To mitigate security certificate issues, enable TLS 1.0 using the Registry Editor:

Step 1.1: Open a Run dialog by pressing Win + R.

Step 1.2: Type regedit and hit Enter.

Step 1.3: Navigate to:

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp

Step 1.4: Look for the “ DefaultSecureProtocols ” DWORD value. If it’s absent, create it:

1. Right-click on the right pane, select “ New ” > “ DWORD (32-bit) Value.” 2. Name the new value as “ DefaultSecureProtocols ”.

Step 1.5: Double-click on “ DefaultSecureProtocols ” to edit its value and enter “ 00000080.”

Close the Registry Editor, then restart your computer to apply the changes. Launch Outlook and check for email reception.

Step 2: Enable TLS 1.2 on the Exchange Server

If you are an IT administrator, add TLS 1.2 to your Exchange Server using the following steps:

Step 2.1: Open Notepad and paste this script:

Windows Registry Editor Version 5.00 [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2] [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client] "DisabledByDefault"=dword:00000000 "Enabled"=dword:00000001 [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server] "DisabledByDefault"=dword:00000000 "Enabled"=dword:00000001

Step 2.2: Save this file as “ Enable-TLS.reg ” by using Ctrl + Shift + S and selecting “ All Files.”

Step 2.3: Double-click the “ Enable-TLS.reg ” file and confirm the action when prompted.

Finally, restart the server and recheck Outlook to ensure the error message is resolved.

Step 3: Test the AutoDiscover Functionality

Verify the AutoDiscover service by performing these steps:

Step 3.1: In the taskbar, find the Microsoft Outlook logo. While holding the Ctrl key, right-click the icon and select “ Test Email AutoConfiguration.”

Step 3.2: Enter your email and password in the provided fields, ensuring to check “ Use AutoDiscover.” Tap “ Test ” to continue.

Once completed, check the logs. If “ succeeded ” appears next to “ AutoDiscover, ” then all is well. If errors persist, consider removing your account and setting it up again.

Step 4: Switch to TCP/IP for Microsoft Exchange

For those using Microsoft Exchange, follow these steps:

Step 4.1: Open Outlook, ignoring any error messages initially.

Step 4.2: Go to the File tab, navigate to Account settings, and access the settings again.

Step 4.3: In the Email tab, select your Exchange email account and uncheck “ Connect to Microsoft Exchange using HTTP.” Save your changes and restart Outlook.

You should no longer see the proxy server error message.

Additional Tips

Always back up your registry before making changes.
Regularly check for updates to Microsoft Outlook and Windows.
Review your network security settings for possible conflicts.

Summary

This guide provided effective solutions to address email issues in Microsoft Outlook post-Windows 11 upgrade. Key methods included enabling TLS protocols and testing the AutoDiscover service.

Conclusion

By following the outlined steps, users can regain access to their Outlook inbox and ensure smooth operation after the transition to Windows 11. Implementing these fixes will improve overall email security and functionality.

FAQ (Frequently Asked Questions)

Why is Outlook not receiving emails after upgrading to Windows 11?

This issue can stem from outdated TLS protocol settings or issues with the AutoDiscover service after the upgrade.

How can I check if TLS is enabled on my system?

You can check the Registry Editor for the DefaultSecureProtocols value or run tests using the Outlook AutoConfiguration feature.