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CalypsoAI

CalypsoAI is an adaptive AI security platform that empowers enterprises to innovate safely—staying ahead of evolving threats to deliver unmatched protection and performance. As a trusted global leader, CalypsoAI partners with organizations of all sizes to responsibly unlock AI’s full potential. Founded in Silicon Valley in 2018 by the most talented minds in AI, data science and machine learning, CalypsoAI has established key partnerships with some of the world’s largest companies and secured backing from investors including Paladin Capital Group, Lockheed Martin Ventures, Lightspeed Venture Partners, 8VC, Hakluyt Capital and Empros Capital. The company has raised $38.2 million to date.

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Founded

2018

Location

New York, NY

Employees

37

Funding

$38M total

CalypsoAI: Trusted AI Security for LLM Apps and Autonomous Agents

CalypsoAI provides AI security software focused on validation, runtime defense, and monitoring at the inference layer. Its platform secures GenAI applications and agentic workflows with automated red teaming, adaptive guardrails, and deep observability—positioning the company as a leader in “trusted AI validation and risk.” Explore the platform and public model rankings via the company’s [homepage and Security Leaderboards](https://calypsoai.com).

Quick Facts

  • Founded: 2018
  • Headquarters: New York, with operations in Dublin
  • Funding: ~$38–40M from Paladin Capital Group, Lockheed Martin Ventures, Lightspeed, 8VC, Hakluyt Capital, Empros
  • Acquisition: Agreement to be acquired by F5 for ~$180M (announced Sept 11, 2025). See the [F5 press release](https://www.f5.com/company/news/press-releases/f5-to-acquire-calypsoai-to-bring-advanced-ai-guardrails-to-large-enterprises), [analysis](https://sitsi.pacanalyst.com/f5-acquires-calypsoai-what-it-means-for-ai-security-for-f5-and-for-customers), and [Paladin note](https://www.paladincapgroup.com/paladin-capital-group-portfolio-company-calypsoai-enters-into-agreement-to-be-acquired-by-f5).
  • Focus: Model‑agnostic AI inference security for applications and agents
  • Core products: Inference Platform, Guardrails, Agentic Red Team, Security Leaderboards
  • What CalypsoAI Does

    CalypsoAI’s platform covers three core security motions across LLM apps and autonomous agents:

    1) Test

  • Automated, agentic red teaming to probe models, apps, and tools
  • Signature Attack Packs and Agentic Fingerprints to systematize attack discovery and benchmarking
  • See [Agentic Red Team and Attack Packs](https://calypsoai.com/insights/agentic-signature-attack-packs) and a [demo](https://www.youtube.com/watch?v=ib_4OEN1KSk)
  • 2) Defend

  • Adaptive runtime guardrails to block prompt injection, jailbreaks, data leakage, and risky agent actions
  • Policy-based controls for tools, actions, and data scopes in agent workflows
  • Learn more about [Secure Agentic AI](https://calypsoai.com/solutions/secure-agentic-ai)
  • 3) Observe

  • Centralized logging and audit trails for compliance and forensics
  • Policy enforcement telemetry, model/app risk scoring, and reporting
  • Public [Security Leaderboards](https://calypsoai.com) to benchmark model resilience
  • For product details, visit the [Inference Platform](https://calypsoai.com/inference-platform) and the company’s [Insights](https://calypsoai.com/insights) and [News](https://calypsoai.com/news) hubs.

    Why It Matters

  • AI attacks are evolving beyond simple jailbreak prompts; autonomous agents introduce tool-use risks and data exfiltration paths.
  • CalypsoAI emphasizes a “zero trust for agents” approach to contain actions and minimize blast radius; see the perspective on [zero trust for agents](https://calypsoai.com/insights/zero-trust-isnt-just-for-people-anymore-securing-ai-agents-in-the-age-of-autonomy).
  • The company’s [Insider AI Threat Report](https://calypsoai.com/news/insider-ai-threat-report) quantifies risky employee AI behavior, reinforcing the need for guardrails and monitoring.
  • Primary Use Cases

  • Block prompt injection, jailbreaks, and sensitive data leakage in GenAI apps
  • Configure and enforce agent policies (tools, actions, data access, and scopes)
  • Red team LLMs, apps, and agents with automated agentic attacks
  • Monitor AI usage with searchable audit logs for compliance and investigations
  • Score model/app risk and benchmark models with public leaderboards
  • Protect agentic workflows that interact with internal systems and third‑party APIs
  • Who It’s For

  • CISOs and security architects requiring runtime guardrails for LLMs and agents
  • Platform/ML engineering teams deploying chatbots, copilots, and agent workflows
  • Risk, compliance, and audit leaders in regulated industries
  • AppSec and red teams assessing AI attack surfaces
  • Integrations and Architecture

  • F5 Integration: CalypsoAI is being integrated into F5’s Application Delivery and Security Platform as AI Guardrails and AI Red Team capabilities. See the [F5 press release](https://www.f5.com/company/news/press-releases/f5-to-acquire-calypsoai-to-bring-advanced-ai-guardrails-to-large-enterprises) and platform context on [securing AI models and agents](https://www.f5.com/company/blog/securing-ai-models-and-agents-without-compromise) and [AI guardrails](https://www.f5.com/company/blog/what-are-ai-guardrails).
  • Model- and provider-agnostic deployment with APIs for embedding into existing apps and platforms. See guidance on [secure integration](https://calypsoai.com/insights/how-to-seamlessly-and-securely-integrate-genai-into-your-existing-systems), [API integration](https://calypsoai.com/insights/api-integration-in-ai-the-technical-backbone), and [operations](https://calypsoai.com/insights/streamlining-operations-the-power-of-effortless-api-integration-2).
  • Partner ecosystem for enterprise delivery and go‑to‑market alignment
  • Note: Specific SIEM, EDR, and LLM vendor integrations are not publicly enumerated; confirm during a demo.
  • Proof and Market Perception

  • Social proof: Named among top AI pen-testing providers by third-party lists ; covered widely during the F5 deal.
  • G2 sentiment: Reviewers cite secure GenAI usage, evaluation/monitoring, and productivity with guardrails; sample size remains small .
  • Capterra: Coverage exists for an earlier “CalypsoAI Toolkit” with governance/integration features; verify parity with the current Inference Platform .
  • Additional comparisons: See third‑party overviews of AI risk tools .
  • Differentiators

  • Model‑agnostic, inference‑layer security that works across apps and agent frameworks
  • Agentic red teaming with Signature Attack Packs and public Security Leaderboards for transparency and benchmarking
  • Runtime, policy-driven guardrails designed for agent tools/actions and data boundaries
  • Research leadership on insider risk and zero-trust patterns for agents
  • Pricing and Trial

  • CalypsoAI announced a free beta at platform launch in 2025; current calls-to-action emphasize demos and sales consultations. Ask about trial or pilot access during evaluation. See the [platform launch update](https://calypsoai.com/news/calypsoai-launches-its-most-advanced-platform-for-securely-building-and-launching-applications-using-genai), [Request a Demo](https://calypsoai.com/request-a-demo), and [Talk to Sales](https://calypsoai.com/talk-to-sales).
  • Evaluation Checklist

  • Confirm: Supported LLMs, agent frameworks, and deployment patterns (on‑prem, VPC, hybrid)
  • Validate: Guardrail performance against prompt injection, jailbreaks, data exfiltration, and tool/action abuse
  • Assess: Logging depth, SIEM export, and audit capabilities for compliance and forensics
  • Test: Agentic Red Team coverage, Signature Attack Packs applicability to your domain, and reporting granularity
  • Review: Integration with F5 environments if you use F5 for app delivery and security
  • Verify: Current product naming vs. legacy “Toolkit,” and feature parity on the latest Inference Platform
  • Ask: Trial/pilot terms, SLAs, roadmap for integrations, and pricing tiers
  • Resources

  • Company and products: [CalypsoAI](https://calypsoai.com) | [Inference Platform](https://calypsoai.com/inference-platform) | [Secure Agentic AI](https://calypsoai.com/solutions/secure-agentic-ai)
  • Research and insights: [Insider AI Threat Report](https://calypsoai.com/news/insider-ai-threat-report) | [Zero trust for agents](https://calypsoai.com/insights/zero-trust-isnt-just-for-people-anymore-securing-ai-agents-in-the-age-of-autonomy) | [Insights archive](https://calypsoai.com/insights)
  • F5 acquisition and strategy: [Press release](https://www.f5.com/company/news/press-releases/f5-to-acquire-calypsoai-to-bring-advanced-ai-guardrails-to-large-enterprises) | [F5 blog context](https://www.f5.com/company/blog/securing-ai-models-and-agents-without-compromise) | [Industry analysis](https://sitsi.pacanalyst.com/f5-acquires-calypsoai-what-it-means-for-ai-security-for-f5-and-for-customers)
  • Partners: [Ecosystem](https://calypsoai.com/partners)
  • Reviews: [G2](https://www.g2.com/products/calypsoai/reviews) | [Capterra](https://www.capterra.com/p/239976/CalypsoAI)
  • Caveats

  • Public, verified customer reviews on G2 and Capterra remain limited; treat sentiment as directional until validated in‑house.
  • Some third‑party listings reference older “Toolkit” branding; confirm features, integrations, and observability depth on a live demo of the current Inference Platform.
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