Certificate Pinning: What Should You Pin First?

Certificate pinning is a security technique where an application is hardcoded to accept only specific certificates or public keys when connecting to a server, rather than trusting any certificate signed by a Certificate Authority. This prevents man-in-the-middle attacks, even if an attacker compromises a CA or tricks a user into installing a rogue root certificate.

Key Insight

The pinning target selection, choosing between certificate fingerprints, public key hashes, or certificate chain elements, is the foundational decision that must come first. This choice establishes your trust anchor methodology and determines security strength, operational complexity, and certificate lifecycle implications. All other decisions (scope, algorithms, rollout timeline) depend on this architectural choice.

Think Like a Manager

The CISSP exam tests your ability to prioritise. When faced with implementation decisions, always identify the foundational architectural choice that all other decisions depend on. Scope, algorithms, and timelines are important, but they cannot be finalised until the core trust model is established. A CISO asks: "What decision, if made incorrectly, will force us to redo everything else?"


Why This Matters

Many teams jump straight to implementation details, debating algorithms or rollout schedules, without first answering the fundamental question: what exactly are we pinning?

Each pinning target creates different trade-offs:

Pinning Target Security Operational Overhead Certificate Renewal
Certificate Fingerprint Highest Highest Requires app update
Public Key Hash High Moderate Survives renewal (same key)
Certificate Chain Moderate Lower More flexibility

The Cascade Effect

Once you've chosen your trust anchor, everything else follows: your backup pin strategy, failure handling procedures, monitoring requirements, and update mechanisms must all align with this foundational choice.

This is why scope decisions, algorithm choices, and rollout timelines, while important, are secondary considerations that must accommodate the trust anchor methodology, not the other way around.

Test Your Understanding

Challenging CISSP practice questions that expose knowledge gaps before exam day.

View Practice Tests
Gagan Singh
Gagan Singh
CISSP, CCSP, PMP

Cybersecurity professional specializing in Critical National Infrastructure protection.