End-of-Support Coming in 259 Days
Every month on Server 2016 costs you more than the last.
See exactly what your migration costs now — and how much that number climbs for every month you wait. Under 2 minutes. No sales call required.
One last step.
Drop your email to get your full breakdown delivered straight to your inbox.
See the full breakdown
-
All 4 options compared side-by-side
-
Personalized recommendation with rationale
-
Cost-of-waiting analysis (in your numbers)
-
PDF emailed for easy sharing
Under 2 minutes
Based on current pricing
No sales call required
The Cost of Waiting
The meter is already running.
Every month you defer the decision, your options shrink and your costs go up. Here's what waiting actually looks like:
+6mo
Your runway disappears
Partner capacity tightens
As EOL approaches, the pool of available migration specialists shrinks fast. Last-minute migrations historically cost 20–40% more than planned ones — and take longer.
+12mo
ESU territory
~75% of a new license
Year 1 ESU costs roughly 75% of buying new licenses outright. Cyber insurance renewals start denying coverage. Auditors flag unsupported OS as a control failure.
+24mo
The math gets brutal
225% cumulative spend
Year 2 ESU doubles Year 1. Combined, you've spent 225% of a new license for zero forward progress. Year 3 adds another 3x. By now, most migrations are emergencies.
75%
Year-over-year ESU increase
40%
Avg. Azure savings with AHB
3-6mo
Typical migration timeline
$0
Cost of getting an estimate
How it Works
Three steps. No spreadsheets.
01
Answer 5 Quick Questions
Version, server count, size, users, and SA status. Takes about 90 seconds. No deep technical inventory needed.
02
Get your 4-path estimate
See directional costs for upgrading, migrating to Azure, buying ESUs, and our recommended path — side by side.
03
Share it with your team
We'll email a branded PDF you can forward to your CFO. Book a call if you want the numbers dialed in for your environment.
Ready to See Your Numbers?
Stop guessing. Get the math.
Your estimate takes 2 minutes. Your migration will take months. Get started on the right path today.
Faqs
Questions, answered.
How accurate are these estimates?
The calculator uses current Microsoft list pricing and typical Azure equivalents. Actual pricing depends on your volume licensing agreement, partner discounts, and specific workload needs. Think of it as a directionally-accurate starting point — typically within 15–20% of final pricing for straightforward environments.
Does running unsupported Server really matter for compliance and insurance?
Increasingly, yes. Cyber insurance underwriters now routinely ask about OS support status — and we've seen renewals denied or premiums raised sharply when clients continue running unsupported Windows Server. PCI-DSS, HIPAA, and SOC 2 auditors all flag unsupported OS as a control failure. Most organizations discover this the hard way, at renewal time or during an audit. It's the quiet cost of waiting that doesn't show up until it's already a problem.
Do I need to share sensitive infrastructure details?
No. We only ask for high-level information: version, rough server count, approximate size, user count, and Software Assurance status. Nothing that would compromise your security posture.
Will I get spammed with sales calls?
No. We'll email you your results and a follow-up with additional context. If you want to talk to a licensing specialist, you book the call. If you don't, we won't push.
What if I'm running mixed versions across my environment?
Pick "Mix of versions" in step 1. The calculator will focus on the oldest version (since that's where the compliance and security risk concentrates) and give you a rough total. For a detailed multi-version plan, book the follow-up call.
Why should I trust MyChoiceSoftware?
We've been a Microsoft licensing partner since 1999. Our team has planned thousands of Server migrations across SMB and enterprise. We make our money by getting the licensing right — not by pushing the most expensive option.
