Pentesting · red & blue team · Sarasota, FL

Penetration testing & red teaming

We attack your web applications, APIs and AI agents the way a real attacker would, prove each weakness we find, help you fix it and test again. The testing runs on Decima Systems, the AI-driven validation service Lennart Lopin (CISSP, CCSP, CSSLP) founded, and a person reviews every finding.

01/ How often

Once a year, or all year

A traditional penetration test is a snapshot. It's often what a rule or an insurer asks for, and it's out of date the next time someone ships a change. Automated testing makes it affordable to test again and again.

POINT IN TIME

A scoped penetration test

One assessment of the applications and APIs you choose, with verified findings, business impact and fixes, then a retest to confirm the fixes. The report gives you the evidence a regulator, insurer or customer asks for.

CONTINUOUS

A standing adversary

The same testing on a schedule, from regular runs toward continuous operation, set by your scope and budget. New releases get tested without anyone having to remember, and every finding's status carries forward until it's fixed.

02/ Red, blue, purple

Attack it, defend it, prove it

Finding weaknesses is half the job. The other half is closing them and showing they stay closed.

Automated attack

Red team

Decima's AI adversary works through your applications the way an attacker would. A model agent runs in an isolated, Kali-style environment with curated security tools, and plans, executes, verifies and records evidence for each attempt. It stays inside the targets, testing windows and stop conditions you signed off on.

Defense

Blue team

Hardening, monitoring and incident readiness for the systems being tested: cloud configuration review (Lennart is a CCSP), secure development practices (CSSLP), and AI-assisted forensics. Lennart's ISC2 Security Congress 2026 talk covered running Claude Code on servers as defensive tooling, from hardening to post-breach forensics.

Find, fix, retest

Purple loop

Every red-team finding becomes a blue-team fix, then a retest that confirms the fix worked. The finding's status carries into the next report, so you can show what was found, when it was fixed and that it stayed fixed.

03/ What we test

Where attackers actually get in

Web applications and APIs

01

Customer portals, booking and ordering systems, admin panels and the APIs behind them. We look for weaknesses an attacker could actually exploit, not a list of theoretical ones.

AI agents and LLM apps

02

Chatbots, AI receptionists and agents that can take actions: prompt injection, what tools the agent is allowed to use, and whether it can reach data it shouldn't. Decima runs this as a pilot service.

Your cloud and servers

03

Blue-team review of how your cloud accounts and servers are configured, who has access, and what is logged, so a finding in the application doesn't become a breach of everything behind it.

04/ Rules of engagement

Scoped, authorized, logged

  • Written authorization, signed by someone who can approve it, before any testing starts
  • Agreed targets, testing windows, stop conditions and data handling
  • Your domain verified by DNS record (verification alone doesn't authorize testing)
  • Exclusions and third-party permissions confirmed, for systems hosted by someone else
  • Every action logged, and every finding reproduced and reviewed by a person before you see it

What the report gives you

  • Verified findings, each with the evidence behind it
  • What each one means for your business, in plain English
  • Practical fixes your developers or IT company can apply
  • Retest results and the date of every test
  • Mappings to ISO 27001 controls, for your compliance file

See a sample Decima report.

05/ Who needs one

When a test isn't optional

FTC Safeguards Rule

Auto dealers, tax preparers, mortgage brokers and many CPA firms must run either continuous monitoring or an annual penetration test plus vulnerability assessments every six months. Firms holding information on fewer than 5,000 consumers are exempt from this part.

PCI DSS

Businesses that store, process or transmit card data need penetration testing at least once a year and after significant changes.

Cyber insurance

Applications and renewals increasingly ask when you last tested your systems and what you fixed.

Your customers

Larger customers and SOC 2 auditors often ask for a recent penetration test report before they sign.

This is general information, not legal advice. Penetration testing is one part of a security program; the rest (risk assessments, policies, a named security lead) is on our cybersecurity consulting page.

06/ Questions

Common questions

Is automated testing a real penetration test?

The testing itself is done by an AI agent with real security tools, attacking within the scope you approved. What makes it a penetration test rather than a scan is that each finding is proven: it's reproduced, evidence is collected, and a person reviews it before it reaches you.

How is this different from a vulnerability scan?

A scan lists things that might be wrong. A penetration test shows which of them an attacker can actually use, and what they'd get. You get fewer, better findings, each with evidence and a fix.

What's the difference between a one-off test and continuous testing?

A one-off test is a snapshot, which is often what a rule or an insurer asks for. Your applications change every month, though. Testing on a schedule, up to continuously, catches what a new release breaks before an attacker does. How often depends on your scope and budget.

Could testing take our site down?

Testing only runs inside the targets, time windows and stop conditions you approve in writing, and we agree in advance which systems are tested in production. If something looks risky, testing stops.

Do you ever test without permission?

No. Testing starts only after a written, signed authorization that names exactly what may be tested.

What does it cost?

We scope every engagement on a free 30-minute call first. Decima Systems publishes its own plans at decima.systems.

Do you only work with businesses in Sarasota?

No. Testing runs remotely for businesses anywhere. Lennart meets clients in person across Sarasota and Manatee counties.

Find it before they do

Tell us what you run and what's driving the question: a rule, an insurer, a customer or a worry. We'll scope a test that answers it.