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Penetration Testing Consultant, Toronto, Canada

Penetration Testing Services for Mid-Market and Regulated Enterprises

Cyber Security Pentesting Inc. delivers penetration testing services to mid-market and regulated enterprises in Toronto and across Canada, with delivery to organizations in the United States as well. Every engagement is scoped, executed, and reported by Arturs Stay, a CREST-registered penetration tester holding OSCP and OSEP, with no subcontracting and no hand-off to a junior analyst.

Scope at a glance: external and internal network testing, web application and API testing, cloud assessment across AWS, Azure, and GCP, Active Directory and Entra ID attack paths, social engineering, red team operations, and AI and LLM red teaming. Compliance-driven testing supports PCI DSS, SOC 2, ISO 27001, PIPEDA, and OSFI B-13 evidence requirements.

Built for CISOs, IT directors, and compliance owners who need exploit-proven findings and a report their board and auditors can act on. Browse every assessment we deliver, or Book a scoping call to get a fixed-price proposal. We find what scanners miss. Vulnerabilities demonstrated, not assumed.

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20+
Years Experience
8
Elite Certifications
5.0
Google Rating
CREST
Registered
red-team-ops · cybersecpentesting.com
$ ./scope-assessment --target enterprise --mode full
✓ Scope defined, external + internal + AD + cloud
$ ./recon.sh --passive --osint --infra
Running OSINT / infrastructure mapping...
✓ 42 hosts discovered · 8 external services
$ ./redteam --ad-attack --lateral --persist
Executing AD attack chains...
→ Kerberoasting: 4 hashes captured
→ Lateral movement: 3 segments crossed
CRITICAL: Domain Admin compromised
$ ./generate-report --executive --technical
✓ Report ready, full findings + exec summary
$
Credentials OSCP OSEP PACES CRTO CRTE CRTP CARTE CARTP CREST CRPT CPSA + View All →
What We Do

Penetration Testing
Services

From full APT simulations to compliance-driven penetration tests, every attack surface, principal-led. Toronto's trusted penetration testing consultant for enterprise security.

01, FLAGSHIP
Red Team Operations
Full-scope adversarial simulations modeled after APT tactics. Physical, digital, and social vectors in one engagement.
APT SimulationC2 FrameworksOPSEC
02
Active Directory Attack
Kerberoasting, DCSync, BloodHound, DACL abuse, and full domain takeover scenarios.
KerberoastingDACL AbuseTrust Attacks
03
Multi-Cloud Security
AWS, Azure, GCP, IAM escalation, misconfigured storage, and cross-cloud attack paths.
AWS / Azure / GCPIAMCSPM
04
Web Application Security
Manual OWASP testing beyond automated scanning, business logic, API abuse, OAuth exploitation.
OWASPAPI SecurityBusiness Logic
05
Compliance Assessments
PCI-DSS, SOC 2, ISO 27001, HIPAA, PIPEDA-aligned testing with board-ready deliverables.
PCI-DSSSOC 2ISO 27001
06, NEW
AI Red Teaming
LLM prompt injection, model extraction, data poisoning, and RAG pipeline manipulation.
LLM AttacksPrompt InjectionRAG

Also delivered: Network & Infrastructure Penetration Testing · Social Engineering · Custom Tailored Pentest · Financial Services Penetration Testing

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Scoping

How engagements are scoped

Every engagement starts with a scoping call. We confirm the systems in scope, the testing window, your compliance drivers, and the level of access to be tested, then you receive a fixed-price proposal for that exact boundary. Timelines follow the scope: a focused single-application or external test is shorter than a red team or multi-environment program, which is planned in phases around your testing window. Testing is followed by a findings debrief, and a retest can be scoped once remediation is complete. For what drives pricing, read our guide to penetration testing cost in Canada. For the full path from kickoff to retest, see our engagement process.

Proof, not promises
★★★★★5.0 on Google· 9 reviews·16+ LinkedIn recommendations

Principal-led delivery, 20+ years of enterprise technology and cybersecurity experience, 15+ industry certifications, including OSCP, OSEP, CREST CRPT, CREST CPSA, CRTO, CRTE, CRTP, CARTE, CARTP, and PACES, banking and regulated-industry experience, and no outsourcing.

Read Google reviews →View LinkedIn recommendations →Why organizations trust CSPI →
Differentiators

Why Enterprises Choose Our
Penetration Testing

Operator Expertise
Principal-Led Every Engagement
Every engagement is personally led by Arturs Stay, OSCP, OSEP, CREST-certified, with 20+ years of enterprise technology and cybersecurity experience. Not delegated to a junior analyst with a scanner.
Real Impact
Exploit-Proven Findings Only
Every critical finding is demonstrated with proof-of-concept exploitation. No theoretical risks, no CVSS score theater.
Full Coverage
Every Attack Surface
Web, infrastructure, AD, multi-cloud, mobile, API, social engineering, physical, and AI/LLM systems under one engagement framework.
Dual Audiences
Reports Built for Two Audiences
Technical teams get precise reproduction steps. Executives get clear risk narratives. One report, zero board-level confusion.
Ready to Start?

Find Your Vulnerabilities
Before an Attacker Does

Get a professional penetration test from a CREST-certified consultant in Toronto. Every day without an assessment is a day your adversaries may be ahead of you.

Request Engagement, Schedule FREE Consultation → Get Help Now

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