5 Red Flags Your Managed Services IT Isn’t the Right Choice

Choosing the wrong managed services IT provider can cost Chicago businesses far more than monthly fees. From unexpected downtime and security breaches to hidden charges and unresponsive support, a poor MSP partnership creates problems instead of solving them. For many Chicagoland organizations, warning signs appear early, but too often go unnoticed until significant damage is done. 

The stakes are high. According to Straits Research, the global managed services market reached $348.12 billion in 2024 and is projected to exceed $1 trillion by 2033. With thousands of providers competing for business, not all deliver the quality and service they promise. Recent data shows that 43% of all cyberattacks target small businesses, yet only 14% are prepared to defend against them. Choosing an MSP without strong security capabilities leaves businesses dangerously exposed. 

This article identifies five critical red flags that signal an MSP partnership isn’t working or won’t work. By recognizing these warning signs early, Chicagoland businesses can avoid costly mistakes and find a provider that truly delivers proactive, transparent, and reliable IT support. 

Why Choosing the Right Managed Services IT Provider Is Critical for Chicago Businesses 

The right managed IT provider becomes a strategic partner that enables growth. The wrong one creates constant friction and drains resources. Technology underpins every business function today, from customer communications to financial management and operational efficiency. 

Chicago businesses face unique challenges that demand expert IT support. Local regulations, industry compliance requirements, and competitive market pressures all require providers who understand the Chicagoland business environment. Growing complexity around cybersecurity, cloud services, compliance, and strategic planning means organizations need more than basic break-fix support. 

Warning signs of problematic MSP relationships often appear during the sales process or early in the partnership. Recognizing these red flags protects businesses from months or years of poor service, unexpected costs, and operational headaches. Research from Verizon’s Data Breach Investigations Report shows that ransomware is present in 88% of breaches targeting small and medium-sized businesses, making the choice of cybersecurity-focused managed service provider more critical than ever. 

Red Flag #1: Managed Services IT Providers With Long-Term Contracts That Lock You In 

Reputable managed services IT providers don’t need to trap clients with multi-year contracts. Long contracts, typically 24 to 60 months, signal lack of confidence in service quality. If an MSP must lock you in contractually, it suggests they know clients would leave once they experience the actual service level. 

This creates real problems for businesses. Technology and business needs change rapidly, but inflexible contracts prevent adaptation. When service quality drops or business requirements shift, companies find themselves stuck paying for inadequate support with hefty early termination penalties blocking any escape. 

Questions to ask about contracts: 

• What is the contract term length? 

• What are the early termination fees or penalties? 

• Can I scale services up or down without penalty? 

If an MSP requires a contract longer than 12 months or won’t discuss month-to-month options, that’s a major warning sign. 

Red Flag #2: Managed Services IT Providers With Hidden Fees and Unclear Pricing 

Transparent pricing is fundamental to honest business relationships. Many managed services IT providers advertise competitive base rates but charge extra for essential services. The pricing shell game leaves businesses facing surprise fees on every invoice. 

Common hidden charges include after-hours support, onsite visits, emergency response, new user setup, and software licensing. Some providers also fail to define how their billing is structured, leading to confusion over what is and isn’t included in the monthly fee. 

Common hidden costs to watch for: 

• After-hours or emergency support fees: Premium charges when you need help outside business hours 

• Onsite visit charges: Extra fees for technicians to visit your location 

• Unclear billing models: Vague definitions of what counts as a service or resource, resulting in unexpected charges 

If a managed services IT provider can’t provide a clear, written breakdown of what’s included versus what costs extra, walk away. Look for providers offering flat-rate, predictable pricing with truly unlimited support. Transparent managed IT services protect your budget and eliminate billing friction. 

Red Flag #3: Your Managed Services IT Provider Has Slow Response Times and Unavailable Support 

Every minute of downtime costs money and productivity. According to Gartner, IT downtime costs businesses an average of $5,600 per minute, which translates to approximately $336,000 per hour. When critical systems fail, businesses need immediate help; not voicemail or tickets that sit for hours. 

Slow response times indicate inadequate staffing or poor prioritization. Red flag scenarios include tickets sitting unanswered for hours, being directed to voicemail instead of live technicians, or hearing “we’ll get back to you tomorrow” when systems are down. 

What responsive support looks like: 

• Clear service level agreements with guaranteed response times 

• Live helpdesk staffed by experienced technicians 

• Escalation procedures for urgent issues 

If an MSP won’t commit to response time guarantees in writing or consistently takes hours to respond to urgent issues, that’s unacceptable. Quality IT help desk support should provide fast, knowledgeable assistance when you need it most. 

Red Flag #4: Managed Services IT Providers That Are Reactive Instead of Proactive 

Reactive managed services IT providers only respond after problems occur. They wait for systems to fail, then scramble to fix the damage. This “break-fix” approach costs more and causes more downtime than proactive IT management. 

Modern MSPs should provide comprehensive proactive support that includes: 

• Continuous monitoring to detect issues before they cause downtime 

• Preventive maintenance that stops failures before they happen 

• Strategic planning that aligns technology with business goals rather than just responding to crises 

Industry research demonstrates that organizations implementing proactive monitoring and maintenance experience significantly fewer system failures and security incidents compared to reactive approaches. 

If a managed services IT provider only contacts you when something breaks or doesn’t conduct regular system reviews, they’re operating reactively, not proactively. Quality proactive IT management and cybersecurity services should prevent problems rather than simply reacting to them. 

Red Flag #5: When Your MSP Has Poor Communication 

Communication issues create frustration and undermine trust in any business relationship. When your IT support provider fails to communicate effectively, it signals deeper problems with their service model and organizational priorities. 

Common communication breakdowns include unanswered emails, missed meetings, lack of status updates, and no consistent point of contact. Businesses need responsive account managers who understand their environment and can explain technical issues in business terms. 

Signs of good MSP communication: 

• Dedicated account manager: Consistent point of contact who knows your business 

• Regular check-ins: Scheduled reviews of service quality and business needs 

• Clear explanations: Technical issues explained in business terms, not just jargon 

The best MSPs assign dedicated account managers who know your business and can translate between technical requirements and business objectives—exactly what virtual CIO services provide. 

Partner With a Managed Services IT Provider That Gets It Right 

Long-term contracts, hidden fees, slow response times, reactive management, and poor communication are five red flags that indicate an MSP partnership may create problems instead of solving them. Chicago businesses deserve better. 

Choosing the wrong managed services IT provider costs more than monthly fees. It results in unexpected downtime, security vulnerabilities, and constant frustration. With ransomware present in 88% of small business breaches and IT downtime costing $5,600 per minute, your choice of managed services IT provider directly impacts your bottom line. 

At LeadingIT, we’ve built our business by avoiding every one of these red flags. We don’t lock clients into long-term contracts. Our pricing is transparent and predictable, with truly unlimited IT support—no surprise fees. Our local Chicagoland teams provide 1-hour-or-less response times with proactive, 24/7 monitoring backed by clear service commitments and responsive account management. 

Partner with a managed services IT provider that gets it right from day one: 

✅ No long-term contracts – stay because we deliver value, not because you’re locked in 

✅ Transparent, flat-rate pricing – know exactly what you’re paying with no hidden fees 

✅ Fast, dependable support – with response times clearly defined in your service agreement. 

✅ Local Chicagoland teams – on-site support available when you need it 

✅ Proactive 24/7 monitoring – prevent problems before they cause downtime 

✅ 14-day instant onboarding – get started quickly without disruption 

Don’t settle for an MSP relationship full of red flags. Schedule a free IT risk assessment to see how LeadingIT delivers transparent, proactive, and reliable IT support for Chicagoland businesses. Call our local IT support team at 815-788-6041 or contact us today to get started.