Core service
Penetration Testing for Businesses
A complete, hands-on security test of the systems your business depends on. Learn what we test, who it's for, what you receive, and how pricing works.
Cybersecurity services · Clearwater / Tampa Bay, Florida
Penetration testing for businesses that can't afford a breach
We safely attack your websites, networks, and cloud systems the way real hackers would — then give you a clear, prioritized plan to fix every weakness we find.
- Fixed-price quotes
- Free retest included
- Supports PCI, HIPAA & SOC 2
PENTEST-REPORT.pdfSAMPLE
Executive Summary — Acme Dental Group
Scope: external network + patient portal
CRITICALSQL injection in portal login allows access to patient records
HIGHVPN appliance running firmware with known remote exploit
MEDIUMNo multi-factor authentication on email admin accounts
LOWVerbose server banners disclose software versions
Fix guidance: step-by-stepRetest: INCLUDED
Illustrative example of the report format. Company and findings are fictional.
24/7Open 24 hours a day, 7 days a week
Fixed priceQuoted before work begins
Free retestIncluded with every engagement
OWASP · PTES · NISTIndustry-standard methodology
What we test
Cybersecurity services built around penetration testing
Every engagement is performed by experienced human testers, not just an automated scanner. Start with our main service below.
Web Application Penetration Testing
Find flaws in websites, customer portals, and online stores, including the OWASP Top 10.
Web app testing details →Network Penetration Testing
External and internal tests of firewalls, VPNs, servers, Wi-Fi, and Active Directory.
Network testing details →Cloud Security Testing
Misconfiguration and access reviews for AWS, Microsoft Azure, and Google Cloud.
Cloud testing details →Social Engineering & Phishing Tests
Measure how your team responds to realistic phishing emails and phone pretexting.
Social engineering details →How it works
A clear, five-step penetration testing process
No jargon, no surprises. You'll know what's being tested, when, and by whom — at every step.
Free scoping call
We learn your goals, systems, and deadlines, then send a fixed-price quote.
Rules of engagement
You approve scope, dates, and contacts in writing. Nothing is tested without authorization.
Testing
Certified testers combine automated scanning with hands-on manual attacks.
Report & debrief
Plain-English executive summary, technical findings, and a live walkthrough call.
Free retest
After you fix issues, we verify the fixes and update your report.
Who we help
Security testing for small and mid-sized businesses
Large enterprises have in-house red teams. Most businesses don't. We give you the same quality of testing, scoped and priced for your size.
- Healthcare & dental practices protecting patient data under HIPAA
- E-commerce & retail meeting PCI DSS requirements
- SaaS & tech startups preparing for SOC 2 or enterprise security reviews
- Law, accounting & finance firms safeguarding client confidentiality
- Any business renewing cyber insurance that now requires testing
What to expect
Clear priorities. Practical next steps.
Discuss your systems, business priorities, and testing scope with our team. Ask how findings will be explained and what support is available for remediation and retesting.
Discuss Your Testing NeedsAbout Online Securitys
The people behind your penetration test
Online Securitys is a Clearwater, Florida–based cybersecurity firm serving the Tampa Bay area founded by Richard Caldwell to make professional penetration testing accessible to growing businesses. We're independent — we don't resell software, so our only job is to tell you the truth about your security.
Every test is led by a named, certified tester you can speak with directly, and all work is performed under a signed authorization and confidentiality agreement.
Talk to Our TeamRC
Richard Caldwell
Founder & Principal. Oversees every engagement and client relationship.
JC
Jason Collins
Lead Penetration Tester
OSCP (Offensive Security Certified Professional), CISSP (Certified Information Systems Security Professional), and CEH (Certified Ethical Hacker). Proficient in Python and Bash, with 10 years of experience.
A
Alexandria
Cloud Security Specialist
Protects cloud infrastructure, data, and applications from cyber threats, misconfigurations, and unauthorized access. Experienced with Cloud Security Posture Management (CSPM), Cloud-Native Application Protection Platforms (CNAPP) such as Wiz, and infrastructure-as-code (IaC) analysis.
Free resource
The small business penetration testing checklist
A practical, one-page guide to preparing for your first pen test: what to scope, who to notify, and which documents auditors and insurers will ask for. Free to download and share.
Request the Checklist- List every public website, portal, and IP address you own
- Identify systems that store customer or payment data
- Confirm testing windows with your IT provider and hosting company
- Name an emergency contact for critical findings
- Gather your compliance or insurance requirements
FAQ
Penetration testing questions, answered
Don't see your question? We're available 24/7 — call (727) 340-3921.
What is penetration testing?
Penetration testing (pen testing) is an authorized, simulated cyberattack on your systems. Our testers use the same techniques real attackers use to find security weaknesses, then show you exactly how to fix them before someone else exploits them.
How much does a penetration test cost?
Cost depends on scope — the number of applications, IP addresses, and user roles. After a free scoping call we give you a fixed-price quote, so there are no surprises. Many small business tests start in the low thousands of dollars.
Will testing disrupt my business?
We agree on testing windows and rules of engagement in writing before we start. Tests are designed to avoid downtime, and we stop and call you immediately if we find anything critical.
How often should a business get a pen test?
Most businesses test at least once a year and after major changes, such as launching a new application or moving to the cloud. Many compliance frameworks, including PCI DSS, require annual testing.
Do you help with compliance?
Yes. Our reports are written to support PCI DSS, HIPAA, SOC 2, ISO 27001, and cyber insurance requirements, and include an attestation letter you can share with auditors, customers, or insurers.
Free 30-minute scoping call
Request your free penetration testing consultation
Tell us about your environment. A senior tester will reply within 24 hours with scope options and a fixed-price quote. No obligation.
- Fixed-price quote before any work begins
- Mutual NDA available on request
- Written rules of engagement and testing windows you approve
We're open 24/7. Prefer to talk now? Call (727) 340-3921