# What Claude (Anthropic) with web search answered for security awareness training (small businesses) on 2026-10-28

## In short

On 2026-10-28, Claude (Anthropic) with web search was asked "best security awareness training for small businesses". It named 16 brands; the first six, in order, were Huntress, G2, flat-fee, per-seat, KnowBe4 and Curricula.

| Fact | Value |
| --- | --- |
| Question | best security awareness training for small businesses |
| Asked on | 2026-10-28 |
| Engine | Claude (Anthropic) with web search |
| Model | claude-opus-5 |
| Brands named | 16 |
| Sources cited | 10 |
| Audience | small businesses |
| Coverage | Coverage: Claude (Anthropic) with web search. Other engines not included. |
| Last verified | 2026-10-28 |

Page: https://bikoosh.com/answers/s/security-awareness-training-small-businesses-2026-10-28
Coverage: Claude (Anthropic) with web search. Other engines not included.

## The answer, as recorded

Asked on 2026-10-28 through Claude (Anthropic) with web search (model claude-opus-5).

> # Security awareness training for small businesses
> 
> Here's what I'd actually recommend, roughly in the order I'd consider them. The right pick depends mostly on whether you have someone to administer it - that's the real fork in the road, more than features.
> 
> ## If you want it fully managed (no admin time)
> 
> **1. Huntress Managed Security Awareness Training** - My default recommendation for most small businesses. It's genuinely managed: monthly episodes and phishing simulations get scheduled and sent for you, with automated reporting. Around **$2.08/learner/month**, and it rates very well (4.9/5 on G2, with users reporting ~1 month to implement). Bonus: if you ever add Huntress EDR/MDR, it's one vendor and one console. ([Huntress](https://www.huntress.com/comparisons/huntress-vs-breach-secure-now), [G2 pricing](https://g2.com/products/huntress-managed-security-awareness-training/pricing))
> 
> **2. Hook Security** - Similar managed philosophy, and the pricing is the most SMB-friendly I've seen: roughly **$2/seat/month, or a $999/year flat rate under 50 seats**. The flat-fee option is great if you're at 25-45 employees, where per-seat pricing is awkwardly expensive. Content leans on humo

## Brands named, in the order the engine gave

| Position | Brand | How it was named |
|---|---|---|
| 1 | Huntress | recommended |
| 2 | G2 | mentioned |
| 3 | flat-fee | mentioned |
| 4 | per-seat | mentioned |
| 5 | KnowBe4 | mentioned |
| 6 | Curricula | compared |
| 7 | CanIPhish | mentioned |
| 8 | Wizer | mentioned |
| 9 | Microsoft 365 | mentioned |
| 10 | Defender | mentioned |
| 11 | Plan 2 | mentioned |
| 12 | E5 | mentioned |
| 13 | Hoxhunt | compared |
| 14 | SoSafe | compared |
| 15 | DefendWise | mentioned |
| 16 | Huntress Managed SAT | mentioned |

## Sources the engine cited

- https://www.huntress.com/comparisons/huntress-vs-breach-secure-now (vendor)
- https://g2.com/products/huntress-managed-security-awareness-training/pricing (review)
- https://www.hooksecurity.co/blog/best-security-awareness-training-small-business (other)
- https://capterra.com/p/10001983/KnowBe4/ (review)
- https://www.knowbe4.com/compare/best-security-awareness-training-for-smbs-in-2026 (vendor)
- https://www.trustradius.com/compare-products/curricula-vs-knowbe4 (review)
- https://caniphish.com/free-phishing-test/phishing-awareness-training (vendor)
- https://www.wizer-training.com/free-phishing-simulation (other)
- https://www.wizer-training.com/faq (other)
- https://www.g2.com/compare/knowbe4-security-awareness-training-vs-sosafe-vs-hoxhunt (review)

The question page: https://bikoosh.com/answers/q/security-awareness-training/small-businesses

Alerts and membership: Answer Watch Pro, 79 USD per month: https://bikoosh.com/answers. Bikoosh is monitoring assistance, not complete protection.

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.