Overcoming the Most Common IT Managed Services Challenges

You partner with a managed IT provider to simplify operations, boost efficiency, and free your internal team to focus on strategy. But when things go wrong like communication gaps, unexpected costs, or unresolved issues, the convenience quickly disappears. 

And with 67% of firms now outsourcing cybersecurity, the stakes are higher than ever to ensure your IT partnership actually delivers on its promise.

“That dependence makes one thing clear, when visibility and accountability fade, outsourcing shifts from value to vulnerability,” as stated by Frank Walsh, VP, WPG Consulting.

This article explores the real-world managed services challenges most organizations face and how you can overcome them before they hurt your business.

When Communication Breaks Down, Everything Else Follows

Most managed IT partnerships fail not because of technical issues, but because of miscommunication. When tickets fall through the cracks, reports are inconsistent, or updates come too late, frustration builds on both sides.

What to do:

• Set clear expectations from day one. Define response times, escalation paths, and who owns what.

• Use shared dashboards so both teams can see performance metrics and ticket status in real time.

• Schedule monthly business reviews, not just for reporting, but for recalibrating goals.

Good communication transforms reactive support into a proactive partnership.

Security and Compliance Are the Biggest Managed Services Challenges Today

On average, there is a hacker attack every 39 seconds. With data breaches and cyberattacks becoming daily news, security is where many managed IT providers are tested and often fall short. With the growing complexity of IT infrastructure and new regulatory demands, MSPs face greater pressure than ever to deliver secure, compliant solutions.

For you, this means ensuring your provider doesn’t just promise compliance, it proves it.

How to stay protected:

• Choose a provider with SOC 2, ISO 27001, or HIPAA certifications.

• Conduct quarterly security audits and discuss the findings together.

• Clarify who is responsible for patching, endpoint protection, and data recovery before signing the contract.

Security isn’t something you outsource, it’s something you share.

Visibility and Control Shouldn’t End at the Contract

Many businesses feel they lose control after outsourcing IT management. Without clear reporting or access to monitoring tools, it’s impossible to measure ROI or understand how your systems are performing.

A transparent provider gives you access to everything they see.

Make visibility non-negotiable:

• Ask for real-time access to dashboards showing uptime, ticket resolution times, and incident trends.

• Request quarterly performance reports that include recommendations for improvement.

• Use service-level data to hold your MSP accountable for measurable results.

Visibility ensures your provider remains aligned with your goals every day, not just at renewal time.

Integration and Onboarding Are Where IT Managed Services Provider Challenges Begin

Switching providers or onboarding a new system can expose just how complex your IT environment really is. Outdated hardware, undocumented processes, and legacy software often slow or break integrations.

This is one of the most overlooked managed services provider challenges and it can make or break your experience.

Smooth onboarding starts here:

• Begin with a detailed IT audit to uncover compatibility issues and risks.

• Create a phased migration plan with milestones, rollback steps, and testing checkpoints.

• Document every system, credential, and integration for long-term consistency.

Good onboarding feels invisible. Poor onboarding feels endless.

Avoiding Managed IT Service Pricing Challenges Through Transparency

Managed IT services can reduce your recurring in-house costs by up to 40% and increase efficiency by 50 to 60%. But while cost predictability is meant to be one of their biggest advantages, hidden fees remain one of the most common complaints. 

When “all-inclusive” doesn’t truly mean all-inclusive, budgets can spiral and the financial benefits of managed IT quickly disappear.

Avoid the surprises:

• Review your SLA carefully and highlight all gray areas, especially “out-of-scope” work.

• Request a pricing model that lists inclusions, exclusions, and escalation rates in writing.

• Ask for regular reviews comparing billed services against contracted scope.

Transparency builds trust, and trust builds long-term value.

Reactive IT Support Is Still Too Common

You shouldn’t have to call your provider to find out something’s wrong. Unfortunately, many still operate reactively, waiting for issues instead of preventing them. That’s one of the most frustrating managed services providers challenges for businesses expecting true partnership.

Shift from reactive to proactive:

• Require preventive maintenance KPIs in your agreement (e.g., “X % of issues resolved before impact”).

• Review recurring tickets every quarter to identify root causes.

• Ensure your provider uses AI-based monitoring or predictive analytics to stay ahead of downtime.

Proactive service turns technology from a burden into a business advantage.

Scalability Is the Long Game

As your business grows, your IT needs multiply. Providers who can’t scale with you will eventually slow you down. Whether it’s onboarding new users, expanding cloud infrastructure, or supporting remote offices, scalability is essential to keeping your IT future-proof.

Plan for growth early:

• Discuss your one-, three-, and five-year plans during the contract phase.

• Include scalability clauses that ensure your provider can grow capacity within a set timeframe.

• Review resource allocation quarterly to maintain consistent response times as you expand.

The right MSP doesn’t just support growth, it enables it.

Choosing a Partner That Minimizes IT Managed Services Challenges

Avoiding the pain points above starts with selecting a provider that’s transparent, accountable, and forward-thinking. Ask tough questions, demand proof of performance, and look for long-term fit, not just quick fixes.

Look for:

• Clear, structured communication processes.

• Security certifications and compliance transparency.

• Real-time visibility into your environment.

• Predictable, no-surprise pricing.

• Scalable support and proactive problem-solving.

With the right partner, managed services challenges become opportunities to strengthen your IT foundation.

Table: Turning Common Managed Services Challenges Into Actionable Solutions

Conclusion: Build an IT Partnership That Works

Every business faces managed services challenges, but the right approach turns them into growth opportunities. When your provider communicates clearly, prioritizes security, and operates proactively, IT becomes a driver of success, not a source of frustration.

That’s where WPG Consulting stands apart. As a leading managed IT partner, WPG Consulting helps businesses overcome complexity, improve security, and scale confidently. Contact WPG Consulting today to schedule a consultation and discover how to make your IT services work seamlessly for your business.