TLS and Microsoft SQL Server 2022

Transport Layer Security (TLS) for SQL Server 2022 has numerous benefits. TLS enhances SQL Server security by providing authentication, encrypting data in transit, ensuring regulatory compliance, and following security best practices. It helps prevent unauthorized access, protects sensitive information, and mitigates interception attacks, making it a critical component of a secure database environment.

Self-Signed Certificates

When installing Microsoft SQL Server 2022 on-premises, a self-signed certificate is automatically created to support Transport Layer Security (TLS) connections to the database. From a security perspective, using unmanaged, self-signed certificates is never a good idea.

Risk

Self-signed certificates are insecure because they are not issued by a trusted Certification Authority (CA), making it impossible to verify the legitimacy of the server. This lack of trust enables attackers to intercept and manipulate data through interception attacks. Additionally, since operating systems do not automatically trust self-signed certificates, users may ignore security warnings, increasing the risk of connecting to malicious or compromised servers.

Enterprise PKI Certificates

For production workloads, security best practices dictate using enterprise PKI-issued and managed certificates, which provide many security benefits.

Authentication

TLS with managed certificates provides a mechanism for server authentication, ensuring that clients connect to a legitimate server and not an impostor. TLS authentication helps mitigate interception attacks where an attacker could potentially impersonate the server. Managed TLS certificates can also be revoked in the event of key compromise.

Data Encryption

Microsoft SQL Server 2022 database servers often store sensitive data, including personal details, financial records, and other confidential business information. TLS ensures that data in transit between the client and the server is encrypted using modern cryptography, which enhances privacy and confidentiality while preventing unauthorized interception and eavesdropping.

Compliance Requirements

Many regulatory frameworks and compliance standards, such as GDPR, HIPAA, or PCI-DSS, require or strongly recommend encrypting data in transit. Enabling TLS on SQL Server helps meet these compliance standards, strengthens internal security protections, and avoids potential penalties.

Security Best Practice

Implementing TLS is considered a fundamental security best practice in network and data communication. It reduces the risk of data breaches and enhances the overall network security posture in the enterprise.

TLS and SQL Server 2022

Microsoft SQL Server 2022 includes critical new options for administrators. The “Force Encryption” and “Force Strict Encryption” flags control how encryption is enforced for client connections, but their behavior and compatibility requirements differ.

Force Encryption

When this setting is enabled, the SQL server will encrypt communication between the client and server using TLS. However, contrary to what the name of the setting implies, it is possible for the server to accept unencrypted connections in some cases. If the client does not support encryption, the connection may still succeed without encryption. Enabling Force Encryption prioritizes encryption but does not strictly enforce it, meaning older clients that do not support encryption can still connect. Administrators can use this setting to ensure backward compatibility for applications that may not support strict encryption policies. However, upgrading applications to support encryption is strongly advised.

Force Strict Encryption

This setting is subtly different than the previous setting. It also ensures that all communication between the client and the server is encrypted without exception. If a client does not support encryption, the connection will be rejected. In addition, this setting enforces enhanced security parameters for the connection, such as certificate validation, more secure TLS cipher suites, and the use of TLS 1.3* when available. Force Strict Encryption is designed for modern security compliance. It is the preferred setting and should be used when all clients are known to support encryption.

* Note: TLS 1.3 is supported with SQL Server 2022 cumulative update 1 or later installed.

Key Differences

The following table summarizes the key differences between Force Encryption and Force Strict Encryption.

Force EncryptionEncourages but does not require encryption. Unencrypted connections may still be allowed.
Force Strict EncryptionRequires encryption for all connections. Clients that do not support encryption will be rejected.

Summary

By securing your Microsoft SQL Server with TLS, you significantly enhance the security, reliability, and trustworthiness of your data management systems. In the next post, I’ll provide detailed step-by-step guidance for enabling and configuring TLS on Microsoft SQL Server 2022 using best security practices.

Additional Information

Step-by-Step Guide: Enable TLS in Microsoft SQL Server 2022

VIDEO: Enable TLS in Microsoft SQL Server 2022

Microsoft SQL Server 2022

Microsoft Deprecates Legacy VPN Protocols

It’s long overdue, but Microsoft has finally announced the formal deprecation of the Point-to-Point Tunnel Protocol (PPTP) and the Layer 2 Tunneling Protocol (L2TP) in Windows Server Routing and Remote Access (RRAS) Servers. Both protocols have long since been replaced with more secure alternatives such as the Secure Socket Tunneling Protocol (SSTP) and Internet Key Exchange version 2 (IKEV2). However, many organizations have RRAS servers configured using these legacy protocols to support ad-hoc, on-demand access for non-managed users and devices.

Deprecated Protocols

There are a few reasons why Microsoft has deprecated these legacy protocols. Consider the following.

PPTP

It’s been widely known for many years that PPTP is broken and terribly insecure. Using this VPN protocol today is tremendously risky.

L2TP

L2TP is still considered secure, for the most part. However, it has been replaced with IKEv2, which is more secure and efficient.

Future Support

Although Microsoft made the announcement recently, the protocols will still be included in Windows Server 2025 when released later this year. However, Microsoft may remove these protocols from future Windows Server releases.

Always On VPN

Those who have deployed Microsoft Always On VPN are likely already using modern, secure VPN protocols, so this deprecation announcement won’t impact them. Although PPTP and L2TP are technically supported with Always On VPN, they are not commonly configured.

Recommendations

Administrators using Windows Server RRAS for VPN access using PPTP are encouraged to migrate to another protocol immediately. Those continuing to use L2TP should consider migrating soon.

Additional Information

Always On VPN Protocol Recommendations for Windows Server RRAS

DirectAccess Fails on Windows 11 24H2

Microsoft recently released Windows 11 24H2. Not long after the release there have been numerous reports of DirectAccess failing after performing an in-place upgrade from previous versions of Windows 11. New installations of Windows 11 24H2 experience the same problem.

Update 10/28/2024: This issue is resolved with KB5044384.

Testing

After downloading and configuring a Windows 11 24H2 test client I was able to quickly reproduce the issue. While previous versions of Windows 11 can connect to my test DirectAccess server without issue, the Windows 11 24H2 client fails.

Troubleshooting

Looking at the DirectAccess status indicator in the UI the DirectAccess connection remains ‘Connecting’ perpetually. Further investigation indicates an IP-HTTPS interface error. Running the command netsh.exe interface httpstunnel show interface reveals an error code 0x57 (invalid parameter) with the following error message.

Failed to connect to the IPHTTPS server. Waiting to reconnect.

Workaround

Currently there is no known root cause for this issue and there is no available workaround. Administrators should delay upgrading to Windows 11 24H2 if DirectAccess is deployed in the organization. I will continue to investigate and post additional information as I learn more. Stay tuned!

Additional Information

Troubleshooting DirectAccess IP-HTTPS Error Code 0x800b0109

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

Troubleshooting DirectAccess IP-HTTPS Error 0x2af9

Microsoft DirectAccess Now Formally Deprecated