Integrating Microsoft Entra with OpenSSL for Secure Authentication and Encryption

The rain hit the glass as the build logs scrolled. Microsoft Entra and OpenSSL were about to meet in a production pipeline for the first time. No second chances.

Microsoft Entra provides identity and access control with hardened security and flexible integration points. OpenSSL handles the cryptography—TLS, certificates, key management. When these two connect, authentication workflows gain both strong identity guarantees and encrypted transport.

The core pattern is straightforward. Use Microsoft Entra to issue and manage tokens. Use OpenSSL to establish and verify secure channels that consume those tokens. This allows services to refuse any connection without a valid Entra-issued credential and a verified certificate chain.

Start by configuring an application in Microsoft Entra. Register your service, define redirect URIs, and set up client secrets or certificates. Download the metadata document. This will contain key endpoints and signing keys.

On the server side, install OpenSSL and configure it to enforce modern TLS (1.2 or higher) with strong cipher suites. Import certificates signed by a trusted CA, or generate them for internal use. With OpenSSL, you can verify the Microsoft Entra public keys against each inbound token. This ensures mutual trust: the client proves its identity through Entra, and the server secures the channel through TLS.

For APIs, combine Entra’s OAuth 2.0 or OpenID Connect flows with OpenSSL-backed HTTPS. During the handshake, OpenSSL negotiates the session, then your application logic uses Entra’s tokens to gate access. This dual-layer approach blocks unauthorized requests before application-level logic even executes.

Test rigorously. OpenSSL’s s_client can connect to your endpoints for debugging handshake failures. Microsoft Entra logs reveal rejected sign-ins and token errors. Check both when troubleshooting.

Used together, Microsoft Entra and OpenSSL provide enterprise-grade authentication and encryption without reinventing protocols or handling raw crypto code.

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