The holidays are supposed to be quiet.
Fewer employees. Fewer meetings. Slower days.

Yet for many businesses, the holidays are when IT problems surface the most.

Servers go down.
Remote access fails.
Backups don’t run.
Security alerts go unanswered.
And suddenly leadership is dealing with IT issues when no one should be.

If your Managed IT Services contract ends in 2026, holiday downtime isn’t just bad timing, it’s a signal.

Why the Holidays Expose Weak IT Providers

Holiday periods stress-test your IT provider more than any other time of year.

Here’s why:

  • Reduced staffing reveals poor escalation processes
  • Delayed responses expose SLA gaps
  • Remote work highlights access and security flaws
  • Cybercriminals target businesses assuming limited oversight

If your provider struggles during holidays, they’ll struggle even more as your business grows in 2026.

This is often when leadership starts thinking:

“We can’t go into another year like this.”

If You’re Planning a 2026 MSP Change, the Holidays Are the Best Time to Evaluate

Most companies wait until renewal notices arrive to assess their IT provider.
That’s a mistake.

The holiday season gives you real-world data, not sales promises.

Ask yourself:

  • Did our provider proactively prepare us for holiday risks?
  • Were systems stable while teams were out?
  • Did response times hold up?
  • Did leadership feel calm or on edge?
  • Were issues prevented or simply reacted to?

These answers matter more than any proposal deck.

The Cost of “Let’s Just Renew After the Holidays”

Renewing out of convenience often leads to:

  • Another year of reactive support
  • Ongoing downtime and employee frustration
  • Increased cybersecurity exposure
  • Budget surprises
  • Leadership staying involved in IT firefighting

By the time Q2 or Q3 hits, many businesses regret not acting sooner.

If your contract ends in 2026, now is your window to plan properly without pressure.

What a Strong MSP Does Before, During, and After the Holidays

A premium IT provider doesn’t disappear during holiday periods.

They:

  • Run pre-holiday risk assessments
  • Validate backups and disaster recovery
  • Secure remote access and endpoints
  • Increase monitoring during low-staff periods
  • Communicate clearly with leadership
  • Ensure zero surprises when teams return

If this didn’t happen for you this holiday season, it’s a red flag worth paying attention to.

Use This Holiday Season to Prepare for a Smarter 2026 Transition

If you’re considering a new MSP for 2026, the best time to start is before renewal pressure sets in.

Early planning allows for:

  • Zero-downtime transitions
  • Proper documentation and onboarding
  • A clear IT roadmap aligned with your business goals
  • Improved security posture before next year’s holidays

Waiting until the last minute limits your options.

A Smarter Next Step Before You Renew

Before committing to another contract cycle, many businesses choose to get a second opinion.

A holiday-season IT review can help you:
✔ Identify hidden risks
✔ Compare your current provider against best practices
✔ Understand what “better” actually looks like
✔ Decide if staying or switching makes sense

No pressure. Just clarity.

Because the Goal Isn’t Just Getting Through the Holidays

It’s entering 2026 with confidence, stability, and an IT partner that makes leadership’s life easier not harder.

If this holiday season raised concerns about your IT support, it may be time to listen.