What Claude (Anthropic) with web search answered for security awareness training (small businesses) on 2026-09-14

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-14

Coverage: Claude (Anthropic) with web search. Other engines not included.

The question asked, verbatim: best security awareness training for small businesses

Brands named, in the order the engine gave

1. Huntress recommended
   Huntress Managed Security Awareness Training (formerly Curricula)
2. Curricula recommended
   Huntress Managed Security Awareness Training (formerly Curricula)
3. KnowBe4 mentioned
   KnowBe4
4. Wizer mentioned
   Wizer
5. Hoxhunt mentioned
   Hoxhunt
6. Mimecast mentioned
   Before buying anything, check: Proofpoint, Mimecast, and Arctic Wolf all bundle awareness training, and Microsoft 365 Business Premium / E5 includes Attack Simulation Training at no extra cost.
7. Arctic Wolf mentioned
   Before buying anything, check: Proofpoint, Mimecast, and Arctic Wolf all bundle awareness training, and Microsoft 365 Business Premium / E5 includes Attack Simulation Training at no extra cost.
8. Microsoft 365 mentioned
   Before buying anything, check: Proofpoint, Mimecast, and Arctic Wolf all bundle awareness training, and Microsoft 365 Business Premium / E5 includes Attack Simulation Training at no extra cost.
9. Microsoft 365 Business mentioned
   Before buying anything, check: Proofpoint, Mimecast, and Arctic Wolf all bundle awareness training, and Microsoft 365 Business Premium / E5 includes Attack Simulation Training at no extra cost.
10. Microsoft 365 Business Premium mentioned
    Before buying anything, check: Proofpoint, Mimecast, and Arctic Wolf all bundle awareness training, and Microsoft 365 Business Premium / E5 includes Attack Simulation Training at no extra cost.
11. CISA mentioned
    CISA and NIST free materials - genuinely decent, zero cost, no phishing simulation.
12. Huntress Managed SAT mentioned
    - Huntress Managed SAT reviews - G2 (https://www.g2.com/products/huntress-managed-security-awareness-training/reviews)

Sources the engine cited

The answer, as recorded

Here's what I'd actually recommend, roughly in the order I'd shortlist them for a small business (say 5-200 employees): **1. Huntress Managed Security Awareness Training (formerly Curricula)** My default pick for most SMBs. Huntress bought Curricula for $22M specifically because it was built for small teams - Huntress's CEO said they evaluated seven vendors and picked it for ease of use and manageability for smaller customers. Story-based episodes, gamified phishing simulator, compliance reporting, and it's genuinely "managed," so you're not building campaigns yourself. If you already run Huntress EDR, it's one console instead of two. [huntress.com/platform/security-awareness-training](https://www.huntress.com/platform/security-awareness-training) · [background on the acquisition](https://www.bankinfosecurity.com/huntress-buys-security-training-provider-curricula-for-22m-a-19616) **2. KnowBe4** The safe, boring, correct answer if your driver is an audit. Biggest content library, role-based paths, and it spits out training evidence for SOC 2 / ISO 27001 / HIPAA / PCI DSS directly - which is the thing most SMBs are actually buying. Per-user pricing (Silver/Gold tiers) that scales with headcount. Less exciting content than the others; people complete it rather than enjoy it. [knowbe4.com](https://www.knowbe4.com/compare/best-security-awareness-training-for-smbs-in-2026) **3. Wizer** Where I'd start if you have no budget and no LMS. Free plan covers 10 users permanently - phishing, passwords, ransomware, social media - with 1-minute videos people don't resent. The paid "Boost" tier adds phishing simulation, the full library, and custom training. For a 10-person shop this may be all you ever need. [wizer-training.com](https://www.wizer-training.com/cyber-security-awareness-training) **4. Hoxhunt** Pick this if your goal is behavior change rather than a compliance checkbox. It's best described as an adaptive phishing engine with training attached - highly gamified, difficulty adapts per user, strong reporting rates. Caveat: it wasn't built for compliance evidence, and teams often end up buying a second platform to cover that. Also priced and positioned more toward mid-market/enterprise than a 20-person company. [hoxhunt.com](https://hoxhunt.com/blog/knowbe4-competitors) **5. Whatever your existing stack already includes** Before buying anything, check: Proofpoint, Mimecast, and Arctic Wolf all bundle awareness training, and Microsoft 365 Business Premium / E5 includes Attack Simulation Training at no extra cost. A free module you'll actually deploy beats a better one you'll defer. **6. CISA and NIST free materials** - genuinely decent, zero cost, no phishing simulation. Fine as a supplement or for a business too small to justify a platform. Two honest caveats. First, a lot of the "best of 2026" listicles in these search results are vendor-owned blogs or affiliate pages ranking themselves - treat the rankings accordingly; I've leaned on the acquisition reporting and vendor pricing pages instead. Second, the platform matters less than you'd think. Monthly phishing simulation plus enforced MFA plus a no-blame reporting culture gets you most of the risk reduction; the brand on the training videos gets you the rest. Sources: - [Huntress Managed Security Awareness Training](https://www.huntress.com/platform/security-awareness-training) - [Huntress Buys Security Training Provider Curricula for $22M - BankInfoSecurity](https://www.bankinfosecurity.com/huntress-buys-security-training-provider-curricula-for-22m-a-19616) - [Huntress Acquires Curricula - Dark Reading](https://www.darkreading.com/cybersecurity-operations/huntress-acquires-curricula-for-22m-to-disrupt-security-training-market-elevate-cyber-readiness-for-smb-employees) - [KnowBe4 - Best Security Awareness Training for SMBs](https://www.knowbe4.com/compare/best-security-awareness-training-for-smbs-in-2026) - [Hoxhunt - KnowBe4 Competitors](https://hoxhunt.com/blog/knowbe4-competitors) - [Wizer - Free Security Awareness Training](https://www.wizer-training.com/cyber-security-awareness-training) - [Huntress Managed SAT reviews - G2](https://www.g2.com/products/huntress-managed-security-awareness-training/reviews)

Markdown edition · the question page, with every recording · Answer Watch · AEO Watch

Answer Watch records what one AI answer engine said on one date, nothing more. Each page names the engine and the model, carries the date the question was asked, and lists the brands that appeared in the answer in the order the engine gave them, with the sources it cited. It is a measurement, not a ranking, not a recommendation and not a claim about the world. Brands that did not appear in an answer are not named on any public page. Coverage: Claude (Anthropic) with web search. Other engines not included.