OpenSSL Conference

This presentation reveals how cloud providers' SSL/TLS implementations pose hidden legal risks due to their systematic violations of stated compliance claims, offering forensic proof and actionable solutions.
I. The Core Problem: The Great Cloud Compliance Swindle and Hidden Legal Risks
•Cloud providers' SSL/TLS implementations are creating hidden legal risks for your organization.
•The core thesis asserts that cloud providers systematically violate their own compliance claims.
•Despite all major clouds advertising FIPS 140-2/3 compliance, a study found that 100% have fallback mechanisms to vulnerable crypto.
•A startling statistic indicates that 78% of enterprises assume cloud providers are fully FIPS compliant according to 2024 Cloud Security Alliance data.
•This issue is not merely technical; it exposes significant legal risks for cloud crypto users.
II. Three Ways Cloud Providers Fake Compliance
1.The Fallback Trick:
◦Providers can silently downgrade to non-FIPS compliant cryptography.
◦For instance, AWS ELB has been observed using AES-128 when under stress, which can be forensically proven through packet captures showing TLS renegotiation patterns.
◦Specifically, AWS Certificate Manager’s non-FIPS fallback modes violate financial regulators’ "safe harbor" clauses.
◦This vulnerability can be exposed via a "Jaw-dropping live demo" or a "Live demo catching a cloud provider mid-fallback to vulnerable crypto". An audit output from such a demonstration might display a warning like: 3/5 TLS connections used non-FIPS AES-128.
2. The Shared Responsibility Shell Game:
◦ Contract loopholes are designed to shift crypto liability directly onto your organization.
◦ A shocking statistic highlights this, revealing that 83% of cloud contracts shift crypto liability to you.
◦ A case study illustrates this risk: a healthcare organization experienced a breach attributed to Azure’s OpenSSL fork, demonstrating how liability is transferred.
3. The Phantom Validation / "Schrödinger's FIPS" Paradox:
◦ This paradox describes how AWS and Azure claim FIPS compliance while simultaneously utilizing non-compliant algorithms.
◦ For example, Azure’s TLS 1.3 implementation uses OpenSSL code that is explicitly banned in EU government systems.
◦ Vendors may claim FIPS certification, but it might apply to only a small percentage (e.g., 5%) of their services, creating a deceptive overall impression.
III. The Legal and Financial Time Bomb
• Recent FTC rulings explicitly make YOU directly liable for your provider's crypto misrepresentations.
• Case Studies of Penalties:
◦ An $8M FTC fine was levied against a healthcare organization for blindly trusting cloud TLS.
◦ A Fortune 500 company was fined $8M for cloud SSL violations, where the flaws were found to be "hiding in plain sight".
◦ A healthcare provider was fined $2.3M despite using "compliant" cloud TLS, with a similar instance citing a financial institution fined $2.3M.
◦ A Fortune 100 company nearly lost a $200M contract due to bogus FIPS claims, underscoring the significant financial impact.
◦ These issues can also lead to violations of GDPR and SEC disclosure rules.
IV. How to Fight Back and Protect Yourself
1. Verify: Do not assume compliance; proactively audit your cloud crypto configurations to expose "how major cloud providers fake their FIPS compliance certifications".
◦ Prove your cloud provider's TLS compliance using openssl s_client commands. For example:
◦ This command represents or can prove your cloud provider's TLS compliance using openssl s_client commands, such as openssl s_client -connect $ENDPOINT -servername $DOMAIN -tlsextdebug -status | grep -A 5 "FIPS" First
{public demo of FIPS validation for cloud-managed SSL}.
◦You can also check TLS configurations more generally using: More generally, openssl s_client -connect your-domain:443 -tls1_2 -tlsextdebug 2>&1 | grep -i "fips" can check TLS configurations
◦ Validate KMS key properties to confirm actual FIPS coverage with commands such as:
aws kms describe-key --key-id alias/your-key | grep -A 10 "FIPS"
◦ Additionally, test IAM policy enforcement to ensure proper controls.
◦ These verification methods provide "court-admissible validation methods" and enable you to "generate legally defensible audit trails with open-source tools".
2. Enforce: Implement stringent cloud-specific FIPS lockdown guides tailored for AWS, Azure, and GCP environments.
3. Contract: Strengthen your contractual agreements with cloud providers.
◦ Include sample clauses such as "Provider must maintain FIPS mode at all times" in your contracts.
◦ Understand the process for filing FTC complaints for false compliance claims made by providers.
◦ Attendees of related talks are provided with a "Sample breach notification letter template for when this blows up".
4. Alternative Architectures:
◦ Consider bypassing cloud crypto entirely for highly critical data that demands the utmost control.
◦ Implement solutions such as HSM-backed service meshes for safeguarding critical data.
V. Free Resources Available
• A Cloud Crypto Compliance Scorecard is available to help evaluate providers.
• The Cloud Crypto Verifier Toolkit (compatible with AWS, Azure, and GCP) is offered. This toolkit is part of a "newly open-sourced verification engine" and represents the "First public release of compliance verification tool".
• A Compliance Letter Generator is provided for demanding verifiable proof from vendors.
• Template demand letters for vendors are also available.
• The "Cloud Compliance Verifier Tool" is accessible on GitHub

VI. Conclusion and key takeaways