Miss Parts 1 or 2? We’ve covered phishing threats and digital clean-up. In Part 4, we’ll close the loop on business continuity planning.

The $50,000 decision: How Alex could navigate his company's Windows 11 transition (a guide for Oregon business owners)

How Oregon SMBs Can Outsmart 2025 Cyber Threats — Part 3 of 4Alex, the fictional but familiar owner of a Salem-based engineering firm with 45 employees, is facing a tough IT milestone. Windows 10 reaches end-of-life in October 2025—and 60% of his company’s machines aren’t compatible with Windows 11.

This isn’t just about upgrades or replacements. It’s about minimizing disruption, staying secure, and avoiding the kind of rushed decisions that rack up avoidable costs.

“For businesses like Alex’s, the key is a strategic approach,” says David Hodgert, Co-Founder of 10D Tech. “Upgrades need to support long-term efficiency and security—not just patch holes.”

Here’s how Alex tackled the transition—and how your Oregon SMB can make the right moves before the deadline.

Alex’s 5-step Windows 11 readiness plan (and what it revealed)

Step 1: Compatibility check

What Alex found:

  • 27 out of 45 computers failed the Windows 11 compatibility test
  • Average age of non-compliant systems: 4.5 years
  • Outdated devices posed clear security risks
  • Sluggish systems were costing $2,500/month in lost productivity

Pro tip: Use Microsoft’s PC Health Check Tool to quickly assess your fleet.

Step 2: Total cost analysis

Alex weighed two scenarios:

  • Upgrade Path:
    - Upgrade 18 compatible machines: $200 each
    - Replace 27 non-compliant machines: $1,500 each
    - Total: $44,100
  • Full Replacement Path:
    - Replace all 45 systems at $1,500 each
    - 15% bulk discount applied
    - Total: $57,375

By comparing cost with expected ROI, Alex began to see where investment made sense—and where it didn’t.

Step 3: Productivity performance

Before upgrade:

  • Employees lost 22 minutes per day to slow systems
  • 3 IT tickets per week generated per aging machine
  • Frequent crashes delayed client projects

Projected after upgrade:

  • 30% faster project delivery
  • 95% reduction in support tickets
  • Smoother collaboration thanks to updated tools

Step 4: Security assessment

Outdated devices couldn’t support current encryption standards and posed compliance risks under frameworks like NIST.

Alex’s assessment flagged hardware vulnerabilities that couldn’t be fixed with software patches—only replacement would do.

Step 5: Future-proof strategy

After consulting with 10D Tech, Alex chose a hybrid path:

  • Replace the 20 oldest machines right away
  • Upgrade 18 compatible machines
  • Phase out the remaining 7 machines by Q3 2025

Post-upgrade results:

  • 32% boost in team productivity
  • No open security vulnerabilities
  • NIST compliance maintained
  • $12,000 saved in annual IT support costs

“Every step—from cybersecurity updates to digital clean-ups—built toward this moment,” says Hodgert. “It’s not about replacing machines. It’s about smart momentum.”

Your Windows 11 transition checklist

  • Run compatibility checks: Use PC Health Check to assess devices
  • Compare upgrade vs. replace costs: Consider both short-term and long-term impact
  • Plan phased transitions: Prioritize machines by age and risk
  • Secure and configure new systems: Harden new devices with managed cybersecurity services

Don’t wait for the October deadline

If you’re like Alex, you’ve already invested in stronger cybersecurity and cleaner infrastructure. Now it’s time to protect that progress with modern systems that can keep up.

Need help? Schedule your free network assessment and get an actionable Windows 11 plan customized to your Oregon business.

This page was last updated August, 2025.

FAQs

Enhanced FAQs:

  • Q: When does Windows 10 reach end-of-life?
    A: October 14, 2025. After that, no updates will be released, affecting over 27% of active SMB machines
  • Q: What happens if I don’t upgrade to Windows 11?
    A: You’ll risk failed compliance checks and security gaps. One SMB in Eugene logged $12,000 in support calls due to outdated machines.
  • Q: How do I know which machines are compatible with Windows 11?
    A: Use Microsoft’s PC Health Check. In Alex’s case, 27 of 45 machines failed compatibility.
  • Q: Can I phase my upgrade over time?
    A: Yes. Alex replaced 20 systems immediately and phased 7 more over 6 months to reduce cost spikes.
  • Q: What’s the average cost to replace a business-grade computer?
    A: Around $1,500. Bulk discounts can reduce this by 15% as Alex discovered in his analysis.