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Rotate certificates

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Applies to: SQL Server

On SQL Server enabled by Azure Arc, Azure extension for SQL Server can automatically rotate certificates for Microsoft Entra ID for service managed certificates. For customer managed certificates, you can follow the steps to rotate the certificate used for Microsoft Entra ID.

Note

Microsoft Entra ID was previously known as Azure Active Directory (Azure AD).

This article explains how automatic certificate rotation and customer managed certificate rotation works and identifies the process specifics for Windows and Linux operating systems.

You can enable either:

Azure Key Vault automatically rotates the certificate for you. Key vault rotates certificates by default, after the certificate lifetime is at 80%. You can configure this setting. For instructions, review Configure certificate auto-rotation in Key Vault. If the certificate has expired, then the automatic rotation fails.

Prerequisite

The functionality described in this article applies to an instance of SQL Server enabled by Azure Arc configured for authentication with Microsoft Entra ID. For instructions to configure such an instance, see:

Service managed certificate rotation

With service managed certificate rotation, the Azure Extension for SQL Server rotates the certificates.

To allow the service to manage the certificate, add an access policy for the service principal with permission to sign keys. See Assign a Key Vault access policy (legacy). The access policy assignment needs to explicitly reference the service principal of the Arc server.

Important

To enable service managed certificate rotation you must assign key permission Sign to the Arc server managed identity. If this permission is not assigned, then service managed certificate rotation is not enabled..

For instructions, see Create and assign a certificate.

Note

There are no specific permissions required for an application to roll its own keys. See Application: addKey.

Once a new certificate is discovered, it is uploaded to app registration automatically.

Note

For Linux, the old certificate will not be deleted from the app registration used for Microsoft Entra ID and the SQL Server running on the Linux machine will need to be manually restarted.

Customer managed certificate rotation

For customer managed certificate rotation:

  1. Create a new version of the certificate in Azure Key Vault.

    In Azure Key Vault, you can set any percentage for the certificate lifetime period.

    When you configure a certificate with Azure Key Vault, you define its lifecycle attributes. For example:

    • Validity period - when the certificate expires.
    • Lifetime action type - what happens when the expiration approaches, including: automatic renewal, and alerting.

    For details about certificate configuration options, see Update certificate lifecycle attributes at the time of creation.

  2. Download the new certificate in .cer format and upload it to the app registration in place of the old certificate.

Note

For Linux, you need to restart the SQL Server service manually so the new certificate is used for authentication.

Once a new certificate is created in Azure Key Vault, the Azure extension for SQL Server checks for a new certificate daily. If the new certificate is available, the extension installs the new certificate on the server and deletes the old certificate.

After the new certificate is installed, you can delete older certificates from app registration because they won't be used.

It can take up to 24 hours for a new certificate to be installed on the server. The recommended time to delete the old certificate from app registration is after 24 hours from the time you create the new version of the certificate.

If the new version of the certificate is created and installed on the server, but not uploaded to app registration, the portal displays an error message on the SQL Server - Azure Arc resource under Microsoft Entra ID.

Next steps