Your IT provider keeps your systems running—but are they really protecting your business from cyber threats and legal exposure?
For many small and mid-sized businesses, outsourced IT is the default solution. But here’s the problem: not all IT providers are security providers—and most don’t take ownership of your cyber liability.
In an era of rising ransomware, regulatory scrutiny, and insurance claim denials, asking the right questions is essential. These conversations can be the difference between a minor incident and a million-dollar loss.
Here are the top questions you should be asking your IT provider today—before the breach, not after.
Why it matters:
Many IT providers assume you'll handle cyber insurance, vendor due diligence, and policy development. If no one’s steering the ship, you may assume you’re protected when you’re not.
What to look for:
A clear breakdown of their security responsibilities
Identification of gaps you’re expected to fill
Willingness to coordinate or partner with cybersecurity experts
Why it matters:
IT performance and cyber liability are not the same thing. You may have backups, but if they aren’t tested or if you lack documentation, you could still lose a claim or face regulatory fines.
What to look for:
Documentation of controls (MFA, backups, endpoint protection)
Experience with insurance questionnaires and breach response
A written incident response plan and support in an actual breach
Why it matters:
Insurers, regulators, and courts don’t just ask what protections you meant to have—they ask what you can prove. Your IT provider should help create an evidence trail that stands up to legal scrutiny.
What to look for:
Dated logs of patching, user access reviews, and monitoring
Written security policies or guidance
Clear records of actions taken (or gaps identified)
Why it matters:
Plenty of firms get hit with ransomware and discover too late that their backups were encrypted too—or that restoration fails under pressure.
What to look for:
Regular testing and reporting
Immutable or offsite backup storage
Documented restore times and procedures
Why it matters:
You don’t want to find out in the middle of a crisis that your IT provider doesn’t handle incident response or legal reporting.
What to look for:
An incident response playbook with clear roles
Defined contacts for forensics, insurance, and legal teams
Prior breach response experience
Why it matters:
It’s one thing to install antivirus. It’s another to help a client survive a class action, an OCR audit, or a denied insurance claim.
What to look for:
Experience with real-world incidents
Support aligning your program with insurance underwriting requirements
Willingness to collaborate with legal and compliance stakeholders
Why it matters:
If your provider won’t stand behind their security work—or refuses to answer due diligence questions from your clients—you may be exposed.
What to look for:
Contractual clarity around roles and responsibilities
Readiness to complete client or regulatory security questionnaires
Partnership mindset—not “we just reset passwords” mentality
Cybersecurity is no longer just an IT issue—it’s a business risk that affects your contracts, compliance, insurability, and even executive liability. You don’t have to become an expert in cyber defense—but you do need to ask better questions and expect better answers.
At Bawn, we help business leaders hold their IT providers accountable—without confrontation or confusion. We work alongside your MSP or internal IT to fill the gaps, reduce liability, and make your program defensible.
→ Want to know what your IT provider isn’t telling you? Schedule a Cyber Liability Readiness Review today.