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How to Fix Global VPN AADSTS500176 Certificate Errors on Mac
Question details
The user is unable to sign into Global VPN on a Mac due to an untrusted or missing issuing certificate.
- Product
- Global VPN
- Device & OS
- macOS
- Scenario
- Attempting to authenticate and sign into Global VPN using a passkey on a Mac.
- Observed behavior
- The sign-in process fails with error code AADSTS500176, indicating that the issuing certificate cannot be found in the trusted certificates list.
Ensure you have macOS administrator privileges and have downloaded the correct client and issuing certificates from your IT department before proceeding.
Install and Trust the Certificate Chain in macOS Keychain
Manually import the required VPN client certificate and its complete issuing chain into the macOS Keychain, then set them to be trusted.
macOS requires the entire certificate chain (client, intermediate, and root certificates) to be present and explicitly trusted in the system keychain for Azure AD authentication to succeed.
Navigate to Applications > Utilities and launch the Keychain Access application on your Mac.
Select the 'System' keychain from the left sidebar. Drag and drop your downloaded certificate files (.cer or .p12 format) into the certificate list.
Double-click the newly imported issuing certificate to open its properties. Expand the 'Trust' section.
Change the setting for 'When using this certificate' to 'Always Trust'. Close the properties window and enter your Mac administrator password to save the changes.
Verify VPN Profile Configuration
Check your VPN client settings to ensure it is actively configured to use the newly trusted certificate for authentication.
Contact Your IT Administrator
If certificates are managed by your organization or mobile device management (MDM) profiles, IT intervention may be necessary to resolve policy conflicts.
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- 1. Download the Installer: Visit the official WPS Office website and download the macOS version.
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Frequently Asked Questions
What does the AADSTS500176 error mean?
This error signifies that the Azure Active Directory (Entra ID) authentication process failed because the issuing certificate presented by the user's device is not recognized or trusted by the authentication server.
Can I fix the AADSTS500176 error without admin rights on my Mac?
No, modifying the System keychain to install and trust root or intermediate certificates requires macOS administrator credentials. You will need to contact your IT department if you lack these permissions.
Why is my passkey failing alongside this certificate error?
Passkey authentication often relies on device compliance and mutual certificate trust. If the underlying certificate chain is broken or untrusted, the entire authentication handshake will fail before the passkey can be verified.
Where can I get the correct issuing certificate for Global VPN?
You must obtain the correct root and intermediate issuing certificates directly from your organization's IT department, intranet portal, or network administrator.
