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A penetration test shows you how a real attacker could get into your Chicago business, before one tries. You get a clear report, ranked fixes and a retest to confirm the holes are closed.
Get a Free IT AssessmentA penetration test is a controlled attack on your own systems. A trained tester tries to break in the same way a criminal would, using your internet-facing services, your Wi-Fi, your staff email, and sometimes your office doors. The goal is not to scare you. The goal is to find out which weaknesses are real, which ones matter, and which ones can wait.
Many Chicago owners already run antivirus and a firewall and assume that is enough. Those tools are only part of the picture. A test shows whether they are set up correctly, whether old accounts still work, whether a forgotten server is exposed, and whether one stolen password could open the whole network. Most businesses find at least a few surprises.
You do not need to be a large company to need one. Law firms in the Loop, medical offices near the Illinois Medical District, accounting firms, manufacturers in the Chicago suburbs and growing professional offices all hold data that attackers want. A test gives you proof of where you stand, which helps with insurers, clients who ask security questions and your own peace of mind.
Cyber insurance applications and client security questionnaires now ask pointed questions. Many ask whether you test your defenses and when you last did. A written penetration test report answers that directly. It also shows you are managing risk on purpose, not hoping nothing happens. For businesses that handle client files, patient records or payment data, that matters in contract talks.
The other reason is cost. Fixing a weakness you found yourself is cheap next to recovering from a break-in. A test points your budget at the problems that are actually exploitable. Instead of buying more tools, you fix the open door first. You also learn what your current IT setup does well, so you do not pay to change things that already work.
Everything below is part of one monthly plan. Pick a topic to see what is handled for you and how it works in a Chicago office.
External testing targets everything an outsider can reach: your firewall, VPN, remote desktop, web portals, email systems and cloud logins. The tester looks for open ports, weak passwords, outdated software and misconfigured services, then tries to use them to get in.
This is the most common first test, and often the most revealing. Businesses regularly find an old server, a test website or a remote access tool nobody remembered was still online. Each one is a door that was left unlocked.
Internal testing starts from the position of a stolen laptop, a phished employee or a guest on your network. The tester checks how far they can move: file shares, other computers, servers, admin accounts and backups.
Many networks are hard on the outside and wide open inside. This test shows whether one bad click would stay small or spread. It also checks how well your devices are separated, patched and monitored.
If you run a customer portal, booking system, online store or internal web app, it can be tested separately. The tester looks at login handling, data exposure, form inputs and how the app treats different user roles.
Web apps often hold the most sensitive data and change the most often. Testing after a major update, or before launch, catches mistakes while they are still cheap to fix. You get specific steps for your developer or vendor.
Wireless testing checks whether someone in the lobby, the parking garage or a neighboring suite could join your network. It looks at encryption, guest network separation and rogue access points. Phishing tests send safe, fake emails to see who clicks.
People are often the easiest way in, so this part is run with care and no shaming. Results show where training would help most. Shared Chicago office buildings make wireless testing especially useful, since neighbors sit a wall away.
Every test ends with two things: a summary for owners and managers, and a technical section for whoever fixes the issues. Findings are ranked by risk and tied to a clear next step. Nothing is buried in jargon.
After you fix the high-risk items, a retest confirms they are really closed. You get an updated letter or report that shows what changed. That is the document most insurers and clients want to see.
Plenty of companies can fix a laptop. These are the three reasons clients mention most when they explain why they picked Ping Chicago.
Your technicians know how Loop high-rises handle building access, why basement server closets flood in summer storms and how long it really takes to reach Oak Brook at 4 p.m. That local knowledge turns into faster, calmer fixes.
Your network, devices and backups are watched around the clock. Most issues are caught and fixed before anyone in your office notices, and the rest are explained to you in plain English.
You get a written per-user quote after a free assessment, with every included service listed. No hourly surprises, no emergency rates and no fine print about what counts as extra.
Chicago offices run in very different buildings and setups, from high-rise floors to small suburban suites. Testing is scoped around how your office actually works, not a one-size template.
Most Loop offices share a building’s internet riser, wiring closets and security desk. Managed IT here means working with property management on access and cabling, keeping remote access stable for commuters and scheduling after-hours work around building rules.
Creative agencies need fast Wi-Fi for large files and constant video calls, while medical offices near Northwestern Memorial need HIPAA-ready systems. Both get the same help desk, with security matched to the data they store.
Teams here grow fast, so new hires need laptops, accounts and access on their first day. Managed IT keeps onboarding repeatable and the network ready for the next floor or the next office.
Dental and medical practices, therapists and small firms run on a few critical systems: scheduling, imaging and billing. Managed IT keeps them patched, backed up and running before the first appointment of the day.
Point-of-sale systems, guest Wi-Fi and a handful of laptops can still take a shop offline. Managed IT separates guest and business networks and keeps payment systems updated and monitored.
Event, hospitality and professional offices near McCormick Place deal with seasonal rushes. Managed IT scales support around busy weeks and keeps shared and public spaces secure.
Practices and offices in Evanston and Skokie get the same remote help desk as downtown clients, with on-site visits scheduled for hardware, cabling and network work.
Logistics and distribution businesses near O’Hare run warehouses, scanners and shipping systems around the clock. Managed IT monitors those networks 24/7 and plans updates outside shift changes.
Many companies in Oak Brook, Naperville and Schaumburg run a suburban headquarters with a city branch. Managed IT connects both sites securely and supports staff at either location.
These three are often confused. They answer different questions, cost different amounts and give different levels of proof.
| Topic | Ping Chicago | Automated Vulnerability Scan | Do-It-Yourself Tools |
|---|---|---|---|
| Who does the work | Trained tester using hands-on methods | Software runs on a schedule | Your staff or a volunteer |
| Finds real attack paths | Yes, tested and confirmed | No, lists possible flaws only | Sometimes, depends on skill |
| False alarms | Reviewed and removed by a person | Common, often long lists | Common, hard to judge |
| Report quality | Plain-English summary plus fix steps | Raw scanner output | Usually none or informal |
| Accepted by insurers & clients | Yes, signed written report | Sometimes, less weight | Rarely |
| Typical cost | Scoped fixed price, quoted up front | Lower, often a subscription | Low cash cost, high time cost |
| Retest after fixes | Included in the engagement | Next scheduled scan | Up to you to remember |
You leave with answers, not a stack of scanner output.
You see which flaws an attacker could actually use.
Every finding is rated so you know what to handle this week.
A signed report you can show insurers, clients and auditors.
A retest confirms the problems are closed, not just patched on paper.
Each industry has different data and different attackers, so testing is aimed at what you actually need to protect.
Client files and email are prime targets, so testing focuses on document access and secure communication.
Healthcare PracticesPatient records need strong protection, and testing supports your security risk analysis.
Financial ServicesAccount data and remote access are checked against the way advisors and staff really work.
ManufacturersPlant networks and office systems are tested without disrupting production schedules.
Our old provider took a day to answer. Now a typical ticket is closed in about 12 minutes, and password resets happen while I’m still on the phone. Our staff stopped complaining about IT within the first month, which never happened before.
We were nervous about changing providers with deadlines ahead. The whole move took three weeks, email and files kept working throughout, and every login and device was documented. Not one person missed a day of work because of it.
We used to get surprise invoices every time something broke. Now it’s one predictable monthly bill, and problems get flagged before we notice them. Planning our IT budget takes five minutes instead of an argument with the owner.
Start with a free IT assessment. You get a written, fixed-price quote for the test before any work begins.
Penetration testing is an authorized, controlled attack on your own systems. A trained tester tries to get in the way a criminal would, then reports what worked. You learn which weaknesses are real, how serious they are and exactly what to fix first.
Cost depends on scope. A small office external test typically costs a few thousand dollars, while larger networks, web apps or multiple locations cost more. Most reputable providers quote a fixed price after a short scoping call, so you know the number before work starts.
A scan is automated software that lists possible flaws. A penetration test uses a person who tries to exploit those flaws and chain them together. The scan says a door might be unlocked. The test shows whether someone can walk through it and what they can reach.
Most small and mid-size tests take one to two weeks of testing, plus time for scoping and writing the report. Larger networks or web applications can take longer. You get a schedule up front, so you know when to expect results.
It should not. Tests are planned with you, and risky actions are avoided or scheduled for off hours. You agree on scope, timing and emergency contacts first. If something unexpected appears, the tester stops and tells you right away.
Most businesses test once a year and after major changes, such as a new office, a cloud move, a new web app or a big software update. Insurers and clients may also ask for a recent report, so annual testing keeps you ready.
If you hold client data, payment details, health records or financial files, yes. Attackers often target smaller companies because their defenses are lighter. A scoped test for a small office is affordable and often finds issues that matter.
It can. Many insurers ask about security testing, and a recent signed report shows you take risk seriously. It may help with your application or renewal, though each insurer sets its own rules, so check with your broker.
You need to name a contact, agree on scope and approve testing windows. Share a list of systems, locations and any no-touch areas. A short call usually covers everything. You do not need to prepare servers or buy software.
You get a report and a walkthrough call. Findings are ranked, with clear fix steps. After you fix the high-risk items, a retest confirms they are closed, and you receive an updated summary for insurers, clients or auditors.
Need something slightly different? These services cover the same ground from another angle.
A free assessment shows what is exposed, what it would take to test it and what it would cost.