Penetration Testing Services in Chicago
Real-world attack simulation that surfaces actual risks. Network and web application penetration testing by certified ethical hackers — find what attackers would find before they find it.
- ✓ Certified ethical hackers
- ✓ Network + web application testing
- ✓ Compliance-aligned (PCI, HIPAA, SOC 2)
- ✓ Detailed remediation reports
Get a Free Pen Testing Quote
A 30-minute scoping call to discuss objectives, scope, and timing for your penetration test.
Vulnerability Scans Don’t Simulate Real Attackers
Scanners find known CVEs systematically. Penetration testers chain them into real attack paths the way attackers do.
Vulnerability scans don’t simulate attackers
Scanners find known CVEs. Pen testers chain them into multi-stage attacks — escalating privileges, moving laterally, exfiltrating data the way real attackers do.
Compliance often requires it
PCI DSS Requirement 11.3, SOC 2 CC4.1, HIPAA risk assessments, NIST CSF — all reference penetration testing as part of mature security programs.
Cyber insurance is asking for it
Underwriters increasingly want recent pen test reports for high-risk verticals (legal, healthcare, financial) and businesses above certain revenue thresholds.
Web apps are unique attack surface
Your web apps speak HTTP. They need testers who speak it too — OWASP Top 10, business logic flaws, authentication bypass, IDOR.
Internal pen tests reveal lateral movement
Once inside the network, how far can attackers go? Internal pen tests answer that — privilege escalation, credential theft, sensitive data access.
Reports drive remediation
A pen test isn’t useful unless the report is actionable — severity ratings, exploitation paths, business context, and clear fix recommendations.
External, Internal, and Web Application Penetration Testing
Six capabilities covering the standard pen testing scope plus the methodology and deliverables that make findings actionable.
External Network Pen Testing
Public IPs, perimeter services, exposed VPN, web servers — the path attackers take from the internet into your environment.
Learn more →Internal Network Pen Testing
Once inside (assumed-breach), what’s reachable? Lateral movement, privilege escalation, access to sensitive data.
Learn more →Web Application Pen Testing
OWASP Top 10, business logic flaws, authentication bypass, injection attacks, and authorization issues for your web apps.
Learn more →Methodology Aligned to PTES/OWASP
Industry-standard methodologies — PTES for network, OWASP Testing Guide for web apps. Consistent, defensible, comprehensive.
Learn more →Compliance-Aligned Reports
Reports mapped to PCI DSS Req 11.3, HIPAA risk assessments, SOC 2, FFIEC, and most cyber insurance frameworks.
Learn more →Remediation Validation
After you fix, we re-test to confirm. Verification is included in every engagement, not billed as a separate project.
Learn more →One Hire vs. an Entire Bench.
Hiring a single in-house IT person costs roughly the same as a full Datastrive managed support agreement — but a single person can’t cover 24/7, can’t be a senior network engineer and a cybersecurity specialist and a vCIO at the same time, and goes on vacation. Managed IT support gives you depth, redundancy, and predictable cost without the recruiting risk.
- Compliance-Aware Engineering. CIS Controls, HIPAA, PCI DSS, and cyber insurance.
- Predictable Flat-Rate Pricing. One monthly invoice covers everything.
- Proactive, Not Reactive. Most issues resolved before your team notices.
- Local Chicago-Based Team. Onsite at your office, not on the other side of a phone tree.
Switching IT Providers Shouldn't Be Painful
Three steps to a calmer environment. Most onboardings are completed inside two weeks.
Schedule Your IT Health Check
A 30-minute call to understand your business, your software, and the IT pain points actually slowing you down.
Onsite Discovery
We visit your office to inventory your network, workstations, and security setup — everything we need to build an accurate proposal.
Tailored Proposal
You get a clear, fixed-price proposal mapped to your team size, your software, and your goals — no surprise add-ons.
Managed IT Support Across Chicagoland
Frequently Asked Questions
Common questions about penetration testing services, methodology, and compliance use cases.
What’s the difference between pen testing and vulnerability scanning?
How long does a pen test take?
Will the test affect production systems?
What’s included in the pen test report?
Does this satisfy PCI DSS or HIPAA requirements?
How often should we pen test?
What does a pen test cost?
Ready to See What Real Attackers Would Find?
Book a free 30-minute pen testing scoping call. We’ll discuss your environment, objectives, compliance requirements, and quote a fixed-fee engagement — no obligation.
- ✓ 30-minute scoping call
- ✓ Methodology & deliverables walkthrough
- ✓ Compliance scope review
- ✓ Response within 1 business hour
Get a Free Pen Testing Quote
A quick scoping call for your penetration testing engagement.