Identify · NIST CSF 2.0

Penetration Testing

We attack your systems the way a real adversary would, before one does.

In Plain English

A penetration test is an authorized, simulated cyberattack on your own business. With your permission and inside agreed rules, we play the role of the attacker to find the weaknesses a real criminal would exploit, prove which ones actually matter, and hand you a plan to fix them before they're used against you.

How It Actually Works

The Technical Reality

Every real intrusion follows a predictable path: the Cyber Kill Chain. A penetration test walks those same seven stages on purpose: we research your business, find a way in, and see how far we can get, all under a signed scope and rules of engagement so nothing breaks.

The methodology is disciplined, not random. NIST's standard (SP 800-115) breaks it into four phases: Planning (we agree scope and rules of engagement, no testing yet), Discovery (we map your systems and find weaknesses), Attack (we safely exploit them to prove what's real and how far it goes), and Reporting (documented throughout). Crucially, we chain weaknesses together the way real attackers do, surfacing risk that no single finding reveals on its own.

How much we're told up front changes what the test reveals: black, grey, or white box. There's no single 'right' one; we pick based on what question you most need answered.

This is different from a vulnerability assessment. A scan produces a long list of things that might be wrong. A penetration test proves which of them an attacker can actually chain together to cause real damage — depth over breadth.

The Cyber Kill Chain

The seven stages of an intrusion (Lockheed Martin). A penetration test walks these same steps — with your permission — to find where the chain breaks first.

  1. 1

    Reconnaissance

    The attacker researches your business — employees, email addresses, and the systems you expose to the internet.

  2. 2

    Weaponization

    They build the attack: a malicious attachment, or a convincing fake login page.

  3. 3

    Delivery

    They send it — almost always a phishing email, link, or attachment.

  4. 4

    Exploitation

    The trap springs: a click or an unpatched flaw lets their code run.

  5. 5

    Installation

    They plant a foothold so they can get back in whenever they want.

  6. 6

    Command & Control

    The compromised machine quietly phones home; the attacker takes the wheel remotely.

  7. 7

    Actions on Objectives

    They do what they came for — steal data, divert a wire transfer, or deploy ransomware.

Source: Lockheed Martin Cyber Kill Chain · mapped to MITRE ATT&CK tactics in our reporting.

How much we know going in

Black Box

Tester knows
Nothing — no credentials, no internal details.
Simulates
An outside attacker starting from zero.
Best for
Testing what's actually exposed to the internet.

Grey Box

Tester knows
Partial — a standard user login or basic architecture.
Simulates
An insider, or an attacker who already phished one account.
Best for
The most realistic real-world breach scenario.

White Box

Tester knows
Everything — architecture, configs, and credentials.
Simulates
A deep audit with full visibility.
Best for
Maximum coverage in the least time.
In Your Business

What It Looks Like For You

For a small or midsize business, a penetration test usually targets your Microsoft 365, your external footprint (whatever faces the internet), your internal network, and your people (a controlled phishing attempt). You won't get a 200-page scanner dump. You get a plain-language report: here's what we got into, exactly how, what it would have cost you, and what to fix first.

The Value

What You Get Out Of It

Proof, not theory

We don't hand you a list of maybes. We show you what's actually exploitable, so you fix what matters instead of chasing false alarms.

Spend where it counts

Findings are ranked by real business risk, so your security budget goes to the gaps an attacker would genuinely use.

Satisfy insurers & auditors

Cyber-insurance applications, SOC 2, and a growing number of contracts now expect a recent penetration test.

Know, don't guess

You'll find out whether your defenses actually hold up against a determined attacker — before a real one finds out for you.

Frameworks & Sources

The Standards Behind It

Lockheed Martin Cyber Kill ChainThe seven-stage model of how an intrusion unfolds.
NIST SP 800-115The federal Technical Guide to Information Security Testing and Assessment.
MITRE ATT&CKThe knowledge base of real attacker tactics and techniques we map findings to.
OWASPStandard methodology for testing web applications.
Start With a Free 30-Minute Conversation

NO PRESSURE.
JUST A PLAN.

Cybersecurity gap, IT problem, or just not sure where to begin? We'll listen first, recommend second, and only propose what actually serves you.

connor@tremodi.com