Evaluating Managed Security Service Providers: What Should Small Businesses Look For?

Choosing the right Managed Security Service Provider (MSSP) can help organizations worry less about cyber risks and focus more on what matters most.  Evaluating the right MSSP to work with can feel overwhelming; vendor pitches, acronyms like SOC, EDR, SIEM, and XDR, and each one promising to be the right fit for your business.

How do you assess which managed security service provider will truly offer the right services for your business without stretching your budget?

Why This Decision Matters

Small businesses aren’t “too small to target.” The 2025 Verizon DBIR shows almost four times as many SMB victims as large organizations, and third-party involvement shows up in 30% of breaches. In other words: the security providers you choose can influence both your vendor-risk and system uptime.

When you engage an MSSP, you're essentially trusting them with visibility into your network, your systems, and ultimately your data. That's not a decision to take lightly. The wrong choice could leave you exposed. The right choice can give you greater peace of mind, expertise you might not be able to afford in-house, and a trusted resource who can truly understand your business.

1) Start with your “must-protect” list

Before you compare MSSPs, write down operational priorities:

• Systems that can’t go down (e.g. POS, ERP/accounting, scheduling, email, VoIP)
• Where your data lives (e.g. Microsoft 365, Google Workspace, SaaS apps, on-prem servers)
• Your endpoints (e.g. Windows/Mac, mobile, shared devices)
• Your users and identity (e.g. MFA, admin accounts, password resets)
• Any compliance pressure (e.g. client requirements, contracts, cyber insurance questionnaires)

This helps prevent a common mistake: hiring a provider that’s great at monitoring logs while your biggest day-to-day risks stay unchanged.

Pro tip: Ask each managed security service provider to map their coverage to your environment on one page: “We monitor X, we manage Y, you own Z.”

2) Confirm what you’re actually buying: MSSP vs MDR vs “monitoring only”

MSSPs may use overlapping terms. The practical difference is simple:

• Monitoring-only: collects logs and sends alerts.
• Managed detection and response (MDR): focuses on endpoint detection + investigation, often with active containment.
• MSSP (broadly): typically provides comprehensive, ongoing cybersecurity monitoring and management across your entire environment; including network, cloud, email security, firewalls, and compliance. MSSPs cast a wider net in terms of infrastructure coverage but focus more on prevention, configuration management, and alert generation rather than deep threat hunting and hands-on incident response
  
  You may want your evaluation to focus less on labels and more on scope + actionability, such as:
• What data sources do they ingest?
• Who investigates?
• Who contains/remediates?
• What’s included vs add-on?

3) Demand “response you can feel” (not just notifications)

An experienced provider should align to recognized incident response lifecycle practices (prep > detect/analyze > contain/eradicate/recover > post-incident improvements).

Ask:

• Do you provide 24/7 human triage?
• Will you isolate a device, disable an account, block an IP/domain, or coordinate with your IT to do it?
• What is your escalation path if my primary contact doesn’t answer?
• Do you run a tabletop exercise with us at least annually?
  
  If the provider can’t clearly explain how they help you contain and recover, you might be want to explore other options.

4) Defense that matches how SMB attacks really happen

The 2025 DBIR dataset includes 22,052 incidents and 12,195 confirmed breaches; attack patterns are well-established, and SMBs are often targets. A credible provider should offer cybersecurity capabilities across these areas:

Identity and access

• MFA enforcement, conditional access guidance
• Admin account monitoring
• Suspicious login detection and response

Email and collaboration

• Phishing and business email compromise protections
• Mailbox rule monitoring
• OAuth/app consent abuse monitoring

Endpoints

• Managed EDR/XDR deployment and tuning
• Device isolation and investigation capability

Vulnerability and patch coordination

• Vulnerability scanning and prioritization
• A clear handoff: who patches? who verifies?

Backup and recovery readiness

• Evidence that recovery is tested (not just “we have backups”)

5) Make SLAs real: time, severity, and “how will you reach me”

Request SLAs that define:

• Time to acknowledge (e.g., critical alerts within X minutes)
• Time to contact you (and backup contacts)
• Severity definitions (what’s “critical,” what’s “high,” etc.)
• After-hours procedures (who picks up, how escalation works)
  
  Also ask how they communicate:
• Phone call for critical issues?
• Ticketing integration?
• Secure chat/channel?
  
  If you’re relying solely on email notifications during an email compromise, you may have already lost time.

6) Reporting that helps you run the business

Reporting should focus on actionable insights rather than surface-level metrics.

Look for:

• Actionable monthly summaries (top risks, what changed, what to fix next)
• Trends over time (phishing attempts, risky logins, vulnerable systems)
• Clear ownership: “Provider will do ___; customer will do ___ by date ___.”

Even better if they can translate findings into budget and roadmap items: what you should fix this quarter to help reduce downtime and risk.

7) Tooling and data: visibility, retention, and portability

Ask these questions early:

• What tools do you use (e.g. SIEM/EDR/XDR/SOAR)? Do we keep licenses if services are discontinued?
• How long do you retain logs, and where?
• Can we get our data exported in a usable format?
• What happens if we terminate the contract; how do we transition cleanly?
  
  Your logs and configurations should remain accessible and exportable, even if services are discontinued.

8) Treat the provider like a high-impact vendor

Your managed security service provider will often have privileged access, so evaluate their controls like you would a bank.

Core expectations:

• MFA everywhere (including support tools)
• Least-privilege access with approvals for admin actions
• Session logging and audit trails
• Background checks for staff with customer access
• Clear subcontractor disclosure (who else accesses your data?)
  
  The Cybersecurity and Infrastructure Security Agency (CISA) guidance for MSPs and their customers highlights risk reduction actions related to managed service relationships and common hardening steps. It can serve as a useful benchmark.

9) Validate their maturity (without getting buried in jargon)

You don’t need an exhaustive audit – just credible evidence:

• Do they have an external assurance report (e.g., SOC 2) or security certifications?
• Do they document playbooks and escalation?
• Can they provide references from similar-size clients?
• Do they measure and improve response performance?

Also ask how they handle modern risk drivers. For example, IBM’s 2025 Cost of a Data Breach reporting cites a global average breach cost of $4.44M and a mean time to identify and contain of 241 days; so speed matters.

10 helpful questions to ask when evaluating a managed security service provider:

1. What’s included in base price vs add-on (EDR, SIEM, email security, vulnerability management, incident response)?
    
2. Do you provide 24/7 investigation by humans? Who covers nights/weekends?
    
3. What actions can you take without waiting for us (containment, account disable, device isolation)?
    
4. What are your SLAs for acknowledge/triage/contact for critical events?
    
5. What do you monitor in Microsoft 365/identity, and what do you not monitor?
    
6. How do you handle vulnerability findings; do you prioritize and track remediation?
    
7. How do you integrate with our IT (ticketing, patch windows, change management)?
    
8. What access will you require, and how is that access controlled and audited?
    
9. Where is our data stored, how long is it retained, and can we export it at any time?
    
10. What does offboarding look like (transition support, data handover, tool removal)?

Bottom line

An experienced MSSP should help reduce operational risk, not simply add another portal and more alerts. 

Prioritize MSSPs that can clearly show: 

1. What they cover in your real environment
2. How they respond when something goes wrong
3. How they keep their own access and processes tight.

Need Help Choosing the Right MSSP?

Evaluating MSSPs shouldn’t feel like guesswork. Acrisure Cyber Services can help you review your current environment, clarify what services you actually need, and help you determine what matters most; response times, reporting, and real support when something goes wrong.

Book a no-obligation chat with one of our cybersecurity professionals and get a complimentary cyber-risk exposure assessment. Reach out to [email protected] or visit Acrisure.com/cyber to get started.
 

^{This content is provided for informational purposes only and reflects common considerations, which may vary based on an organization’s size, industry and risk profile.}