Offensive Security

Red Teaming Exercise: BEC & AiTM Attack Simulation

You can’t know how your business would hold up against a Business Email Compromise or Adversary-in-the-Middle attack until someone tests it properly. CloudGuard’s Red Teaming Exercise simulates that exact attack, safely and under control, so you get board-level assurance and a clear, evidenced answer: could this happen here, and how fast would we catch it? 

100s of businesses continue to improve their cybersecurity with CloudGuard

WHAT WE TEST

What We Actually Look At and Why Each Piece Matters to You

Every part of this engagement targets a different piece of the same question, not isolated checks, but a connected view of where a real attacker would get through, and where they wouldn’t.

Phishing-Led Attack Simulation

A controlled BEC and AiTM campaign built on the tactics real threat actors use, not a generic phishing test. It matters because a simulation only proves something if it mirrors what you’d actually face. 

Identity & Access Control Validation

We test your MFA, Conditional Access and identity controls against modern session-hijacking techniques, not just credential theft. It matters because having MFA enabled isn’t enough in today’s threat landscape, weak methods can still be exploited. 

Detection & Response Assessment

We measure whether your monitoring and alerting actually catch the campaign in flight, and how your team responds under pressure. It matters because a control that isn’t watched is a control you’re only assuming works. 

Threat Intelligence & Reconnaissance

We map the same public information and attack paths a real adversary would use to target your people. Attackers don’t guess who to target, they research, and so do we. 

HOW WE WORK WITH YOU

From First Conversation to Board-Ready Answer

Security testing loses people when it feels like a black box. Here’s exactly what happens, in order, so you know what to expect before anything starts.

Phase 1: Engagement Initiation

Together we agree scope, objectives, target groups and rules of engagement. Then, register the campaign domain. Nothing starts until you've signed off exactly what "in scope" means.

Phase 2: Reconnaissance & Planning

We identify realistic target users and build attack scenarios that reflect how a real adversary would approach your organisation, not a generic template.

Phase 3: Campaign Execution

We run the controlled BEC and AiTM phishing campaign, replicating real-world toolsets and techniques against the agreed user population, safely and within bounds.

Phase 4: Detection Assessment

Throughout the campaign, we assess how effectively your monitoring, alerting and incident response actually perform, in real time.

Phase 5: Report & Recommend

You receive campaign metrics, prioritised findings and a clear remediation roadmap, built for both technical teams and the board.

Phase 6; Data & Infrastructure Purge

Every asset used during the engagement is digitally destroyed. Nothing lingers, nothing to clean up on your side. 

Security Done Different

One Engagement, Compounding Value Across Everything You Do Next

CloudGuard is a Microsoft Security Specialist, not a generalist IT reseller. We simulate the actual attack path through Entra, Conditional Access and Defender, testing what those tools are meant to stop, not just how they’re deployed or licensed. This is a genuine Red Teaming Exercise, not a phishing awareness exercise: it isn’t a click-rate report or passive monitoring after the fact. It proves whether your defences and your people would actually catch a modern attack as it happens. 

Readiness

By showing you, with evidence rather than assumption, closing the gap between what you believe is covered and what's genuinely tested. 

Responsiveness

Because your team experiences a live, realistic attack in progress, not a tabletop hypothetical.

Resilience

Your remediation roadmap doesn't sit on a shelf. it feeds directly back into hardening identity controls, tuning detection, and improving the next test.

IS THIS YOU?

Built for Teams Who Need to Answer "How Exposed Are We?" With Evidence

Typical buyers: CISO / Head of Security, IT Director, Compliance & Risk Officer, anyone who needs to answer “how exposed are we, really?” with evidence rather than assumption. 

Configured, But Never Battle-Tested

If you have a Microsoft 365 or a hybrid identity environment with MFA and Conditional Access already configured, and want proof it holds up against modern attack techniques. Whether that’s for a new CISO’s 90-day baseline review or after a phishing near-miss.

Facing an Audit, Renewal, or Milestone

You’re preparing for cyber insurance renewal, an audit, or a compliance milestone (ISO 27001, Cyber Essentials Plus) and need evidenced testing, not a policy statement.

When the Board Asks, You Need an Answer Ready

You need board-level assurance backed by a prioritised roadmap their team can act on immediately, plus real validation of whether security awareness training is actually working.

Trusted by Customers. Backed by Certifications. Proven in the Real World.

CloudGuard is embedded in the cybersecurity industry – recognised, accredited, and trusted to protect real organisations every day.

Not what you’re looking for?

Related services

Cyber Incident Response Planning

A series of workshops designed to develop and test your incident response readiness in response to various forms of cyberattacks.

Red Teaming

Find out whether your organisation could withstand a genuine attack, not just whether it looks secure on paper.

Purple Teaming

Find out how well your organisation prevents, detects and responds to realistic attacker behaviour, with your own team involved every step of the way. 

Frequently Asked Questions

How is BEC and AiTM red teaming exercise different from a phishing simulation training tool?

Phishing simulation tools measure whether users click a link, useful, but limited. This engagement replicates a real adversary’s full technique: session hijacking that bypasses MFA, not just credential capture. It tests your identity controls, your monitoring, and your incident response together, under realistic conditions, and hands back evidence-based findings your board and insurer can actually rely on. 

No. The engagement is scoped and agreed with you upfront, target groups, rules of engagement, and boundaries are all fixed before anything runs. It’s a controlled simulation using isolated infrastructure, not a live attack against production systems. Once complete, all campaign infrastructure and data are digitally destroyed. You get the insight of a real attack attempt without the exposure of one. 

Penetration Testing looks for exploitable technical weaknesses across your systems, broad coverage, less realism. Purple teaming is collaborative: your team and ours work together in real time to tune detection. This engagement is closer to a genuine attack: a covert, scenario-led simulation of BEC and AiTM techniques against real users, testing whether your people, controls and response would catch it without knowing a test was coming. 

Yes, and that’s exactly who this is for. Having MFA configured tells you a control exists; it doesn’t tell you whether it stops the specific technique, session hijacking, that modern AiTM kits are built to bypass. This engagement tests that gap directly, so you know whether your existing investment is actually holding, rather than assuming it. 

Most engagements run across several weeks, covering scoping, reconnaissance, the live campaign, and reporting. You receive a prioritised findings report with campaign metrics, evidenced gaps in identity, monitoring and response, and a clear remediation roadmap, written for both your technical team and your board, so everyone leaves with the same understanding of where you stand. 

CloudGuard’s Red Teaming Exercise is available from ÂŁ12,999, price varies depending on the size of organisation and scope. This covers the full lifecycle from reconnaissance and campaign execution through to reporting and remediation guidance. If your environment, user population, or objectives fall outside a standard scope, we’ll price a custom engagement to match instead, so you’re never paying for more than you need. 

Yes. The engagement produces a documented, evidence-based assessment of your resilience against a named, current attack technique, exactly the kind of proof insurers and auditors increasingly ask for over policy statements alone. Findings map clearly to remediation actions, giving you a defensible position to bring to renewal, audit, or board review.

Pricing

Pricing You Can Actually Take to Your Board

CloudGuard’s Red Teaming Exercise: BEC & AiTM Attack Simulation is available as a fixed-cost of £12,999, for organisations that fit a standard scope, giving you transparent, predictable pricing from the outset. Where your environment, user population, or objectives need a tailored approach, we scope a custom engagement to match, priced against exactly what you need, not a generic package. 

FROM
ÂŁ12,999
NEXT STEP

Stop Assuming. Start Knowing.

You don’t need to wonder whether your defences would hold up against a modern BEC or AiTM attack. Find out, with evidence you can bring straight to your board, your insurer, or your next audit. 

Talk to CloudGuard about our Red Teaming Exercise.