Thought Leadership

The five questions CISOs are asking. Here is where we stand.

The same five questions anchor our front page. This is where we answer them at depth, with arguments published in the security press and shaped by 5,000 detections of what is landing in inboxes today.

Question 1

How is AI enabling attackers?

The economics of attack just inverted. Personalization used to cost attackers time. Now it costs them nothing. Every defense built on the assumption that attackers would not bother just became economically obsolete, and the SOC budget is the line item that pays for the mismatch. This pillar is the single largest shift in email security since the category was created.

Anthropic disclosed 500 zero-days. CISOs should worry about the communications layer, not the CVE count.

When AI models autonomously discover and chain vulnerabilities, the exploit supply becomes infinite. The chokepoint is not patching, it is how attackers deliver the payload. That chokepoint is email.

Read in SC Media →

AI agents are man-in-the-middle attacks with a user experience layer.

The parallels between AI agent architectures and classic MITM exploits are closer than the industry wants to admit. Every trusted intermediary is a potential pivot point, and agents are the most trusted intermediary we have ever deployed.

Read in Security Boulevard →

AI rewrote the economics of email security overnight.

Personalization used to cost attackers time. Now it costs them nothing. Every defense built on "attackers won't bother" is now economically obsolete, and your SOC budget pays for the mismatch.

Read in TechRadar Pro →

It takes only 250 documents to poison any AI model.

RAG poisoning is the new supply chain attack. The integrity of every AI-powered defense now depends on the provenance of the corpus it trains on, and most vendors cannot document theirs.

Read in Dark Reading →

GPT-4-powered MalTerminal is the canary, not the outlier.

Researchers uncovered malware scaffolded and operated by a commodity LLM. StrongestLayer research cited on prompt injection, LLM poisoning, and what it means when attack tooling becomes a prompt.

Read in The Hacker News →

Jailbroken LLMs are the new dark-web marketplace for phishing.

Extended interview on AI-driven attack economics, the mid-market security gap, and why "good enough" email security becomes catastrophic the moment attackers automate their side of the workflow.

Read in BetaNews →
Question 2

How has the threat landscape expanded?

Your stack triages to 2 labels. The attack surface is 44. Phishing and BEC was the useful abstraction of 2015. In 2026 it hides what has actually changed. 35.9% of what lands in inboxes today is structurally impossible for a gateway to block, and whitelists, partner domains, and trusted platforms are the new attack surface nobody budgeted for.

27.8% of phishing is now telephone-delivered, and your SEG cannot see a voice channel.

Multi-channel evasion is the new default. A clean email with a phone number routes the payload through a conversation your email security never sees. Based on StrongestLayer analysis of 5,000 detections.

Read in Dark Reading →

Microsoft 365 has a side door, and every major SEG walked past it.

StrongestLayer research exposed attackers abusing M365 Direct Send to spoof internal users at scale. Every legacy gateway in our test set missed it. The lesson is not the vulnerability, it is the detection assumption.

Read in Dark Reading →

Whitelists are the single largest unmonitored exception in your zero-trust program.

Every email allow-list is a standing permission slip for attackers who compromise a trusted sender. Zero trust that stops at the email layer is not zero trust. It is a budget line item.

Read in Security Boulevard →

Five questions your security team should answer before defending another whitelist.

Practical companion to the Zero-Trust Paradox argument. Five pointed questions a CISO can bring to their email team that surface exactly how many attackers are already trusted by default.

Read in SC Media →
Question 3

How do you catch these new attacks?

We don't scan messages. We render them. Signatures tell you what you already know. Reasoning tells you what you are actually looking at. Every email security product will become a reasoning engine or become a legacy entry in a competitive battlecard. There is no middle ground and no five-year glide path.

Dual-evidence architecture is the only honest answer to AI-generated phishing.

Signatures tell you what you already know. Context tells you what you are looking at. Next-gen email defense needs both, running against each other, not either one running alone.

Read in SC Media →

Conway's Law explains why legacy SEGs cannot become AI-native.

A system reflects the communication structure of the team that built it. Gateway architectures built on rules and committees produce rules-and-committees products. AI-native detection requires AI-native organizational design, not a feature port.

Read in Computer Weekly →

Three questions that separate an AI security vendor from an AI-branded one.

A CISO evaluation framework for AI security vendors that cuts past the marketing layer. What the model sees, what it retains, and what it can actually reason about in production.

Read in SC Media →
Question 4

How do you help me block and investigate faster?

Evidence ships with every verdict. Security training moved from defense to self-sabotage the moment AI eliminated the cues users were trained to spot. Every minute your analyst spends reproducing the AI's verdict is a minute they are not spending on the next attack. Fast response starts with evidence that arrives with the decision, not evidence the SOC has to reconstruct.

Security training is now your biggest security risk.

The tells we taught users to spot (typos, pixelated logos, grammatical errors, mismatched URLs) are exactly what LLMs eliminated. When the training data is stale and the attacker has fresh data, the training becomes misdirection, and the SOC absorbs the cost.

Read in Security Boulevard →

DocuSign phishing is the single most common top-inbox threat, and analysts are triaging it blind.

StrongestLayer research cited on the live rate of trusted-platform abuse. The operational implication: analysts need evidence at the platform-interaction layer, not just the message layer, to triage without reconstructing each incident from scratch.

Read in SC Media →
Question 5

How do you keep our data private?

We detect without exposing. AI-native security has an uncomfortable truth at its core: the most powerful detection traditionally demands the most invasive access. That trade-off is a design choice, not a physical law. Zero retention, zero training on customer content, and evidence-based reasoning are architectural, and they can be audited.

Privacy Architecture v1.3: The technical details.

The architectural teardown for the CISO and legal reader. Complete documentation of zero-retention detection, architectural audit points, and what happens to your data during analysis and after verdict delivery.

Read on Privacy Architecture page →
In Conversation

Podcasts and speaking.

Longer-form sessions where the arguments above get pressure-tested live. Useful if you want to hear Alan work through these ideas unscripted.

Podcast · Category Visionaries / Frontlines.io

How 85% POC win rates get built, and why category creation starts with honesty.

Oct 2025 · GTM-focused founder interview

Listen on Frontlines →
Podcast · The Cloudcast #965

LLM reasoning in email security, and why pattern matching is dying.

Oct 2025 · Deep technical discussion

Interview Series · Unite.AI

LLM-native architecture, the TRACE engine, and the 2026 to 2027 threat landscape.

Sep 2025 · Long-form feature

Read on Unite.AI →
CEO Profile · Pulse 2.0

The founding thesis, the dual-evidence model, and why email is the fulcrum.

Sep 2025 · Full-length interview

Read on Pulse 2.0 →
Keynote · FutureCon CyberSecurity Conference

Fake Rolex, Real Satisficing: how stacked evasion exploits the modern inbox.

AI-generated phishing and why cognitive shortcuts defeat legacy controls

Webinar · Cloud Security Alliance Delaware

AI-generated email attack prevention: a 50-minute walkthrough.

Sponsor session, full recording available

Looking for the evidence underneath these arguments?

The arguments above are the thesis. The 44-subtype taxonomy, the kill-chain simulations, and the detection-gap breakdowns are the proof. Sent separately so each reader gets the view that matches their job.

Go to threat research →

Your gateway can't see what's already inside.

Request a threat briefing with the team that publishes this research. 30 minutes, no slides, no pitch. We will walk through what we are seeing in live traffic and what it implies for your stack.

Request a Threat Briefing →