CalypsoAI vs F5 AI Guardrails

CalypsoAI was an AI security company founded in the US in 2018 by Neil Serebryany, its first CEO; it describes itself as founded in Silicon Valley, and its early press releases carry Washington datelines. It began with software for testing, validating and monitoring AI and machine learning models for national security, finance and other regulated customers, and moved to securing generative AI with CalypsoAI Moderator in 2023. Donnchadh Casey became CEO in August 2024. In October 2024 CalypsoAI named Dublin its global co-headquarters, alongside a US headquarters in New York; IDA Ireland says the CEO, the CTO and most of its R&D were based in Dublin. Paladin Capital Group led its $13 million Series A (July 2020) and a $23 million Series A-1 (June 2023), and F5 says it raised more than $40 million in venture funding. Investors also included Lockheed Martin Ventures and Hakluyt Capital. F5 announced on September 11, 2025 that it would acquire CalypsoAI for $180 million in purchase consideration, mostly cash. F5's 10-Q says the deal closed on September 26, 2025 and records $145.2 million in cash consideration. CalypsoAI is no longer sold separately: calypsoai.com now redirects to F5's AI Guardrails page. F5 introduced F5 AI Guardrails and F5 AI Red Team when it announced the close, and made both generally available in January 2026. Buyers should evaluate those products. **What it sold** By 2025 CalypsoAI sold an inference security platform with two main products. Inference Defend checked prompts and responses in real time to block prompt injection, jailbreaks and sensitive data leakage, using custom scanners that could be versioned, tested and enforced per project. Inference Red-Team ran automated and agent-driven multi-turn attacks, drawing on more than 10,000 new attack prompts a month, and produced a risk score. The platform logged AI interactions for audit, sent logs to Splunk, and ran as SaaS, on premises or hybrid. In August 2025 CalypsoAI said an on-premises version of Red-Team, for organizations with strict data residency or air-gapped requirements, would soon be available in early access. **Frameworks** In August 2025 CalypsoAI added an EU AI Act scanner package to Inference Defend, covering four Article 5 prohibited-practice categories: manipulation, social scoring, biometric data harvesting and surveillance. F5's deal announcement said its governance features help customers meet GDPR and EU AI Act requirements. We found no CalypsoAI mapping to the NIST AI RMF or ISO 42001.

F5 AI Guardrails is F5's runtime security product for AI models, applications and agents. F5 sells it alongside F5 AI Red Team, its automated adversarial testing product, and presents the two as a pair: findings from Red Team can be turned into guardrail policies. Both come from CalypsoAI, the AI security company F5 announced it would acquire on September 11, 2025 for $180 million in purchase consideration, mostly cash. The deal closed on September 26, 2025. F5 introduced both products when it announced the deal had closed, and made them generally available in January 2026 as part of its Application Delivery and Security Platform. F5, Inc. was incorporated in 1996 and is based in Seattle; this profile lists the company's founding year and headquarters, as the directory does for other big-company products. F5 AI Guardrails blocks prompt injection and jailbreaks, detects and prevents leakage of personal data and custom data categories, filters toxic or harmful output, and audits or blocks unauthorized tool calls and actions by agents. Policies can be written in natural language. Every enforcement action is logged with attribution, and logs can be exported to third-party SIEMs. It works with any model and runs in AWS, Azure or Google Cloud, in private clouds, or on premises, including fully air-gapped environments. F5 AI Red Team sends a swarm of attacker agents to run static, prompt-based and multi-turn attacks, including indirect prompt injection and data-leakage tests on RAG applications. F5 says its attack library grows by more than 10,000 patterns a month. Red Team runs in the major public clouds or on premises as a certified Red Hat OpenShift operator. A feature called F5 AI Remediate drafts guardrails from Red Team findings, and a person approves each one before it goes live. **Gateway and platform** On June 22, 2026 F5 launched the F5 AI Security Platform, which groups AI governance, AI discovery, testing with AI Red Team and runtime protection with AI Guardrails, plus an audit trail across AI interactions. At the same time it announced the acquisition of SurePath AI, which adds network-based discovery of AI use, including shadow AI. F5's AI Gateway now combines a model gateway, an MCP gateway (with an MCP server registry and per-tool allow and deny controls) and AI Guardrails under one control plane. **Compliance coverage** F5 says Guardrails has automated auditing templates for GDPR, HIPAA and the EU AI Act, out-of-the-box policy controls aligned to PCI, PHI and the EU AI Act's prohibited-risk categories, and audit-ready logs. It also says Red Team findings can support compliance programs aligned with the NIST AI RMF and the EU AI Act, and it publishes an infographic aligning its products with the OWASP Top 10 for LLMs. We found no article-by-article mapping to the EU AI Act. **Who it's for** Large enterprises, including regulated financial services and healthcare organizations, that need AI guardrails they can host themselves or run air-gapped. F5 says both products are deployed at Fortune 500 companies. It also suits F5 customers who want AI controls on the same platform as their application delivery and API security.