Are Microsoft Licenses Really That Valuable?

If you’ve tried sourcing Microsoft licenses recently—especially volume licenses—you might’ve felt like you were hunting for digital gold. Between rising prices, complex compliance rules, and supply constraints, it’s no longer just a line item on your procurement checklist.

So why does it feel like Microsoft licenses have become the “crypto” of the IT world? Let’s break down this surprising, but increasingly accurate, analogy—and why it matters for IT leaders, procurement teams, and MSPs alike.


The Microsoft Licensing Market: A Digital Asset?

1. Scarcity Creates Value

Like cryptocurrencies, Microsoft licenses—particularly legacy licenses and on-prem solutions—have become harder to find as Microsoft shifts aggressively toward cloud subscriptions. This scarcity has led to:

  • Higher resale values
  • Increased demand in secondary markets
  • Third-party vendors stepping in to meet needs

2. Licenses Hold Real-World Utility

Crypto has utility in the decentralized world. Similarly, Microsoft licenses are critical to business operations:

  • Windows Server CALs keep infrastructure compliant
  • Office 2019 perpetually licensed versions avoid SaaS renewals
  • SQL Server licenses are vital for data-heavy industries

The right license = operational stability.

3. They’re Traded Like Assets

Businesses now buy, sell, and audit licenses with the same seriousness as financial assets:

  • Secondary license marketplaces have emerged (e.g., UsedSoft, Discount-Licensing)
  • Volume license agreements are scrutinized for ROI
  • Compliance risks can trigger audits, fines, or forced upgrades

Why IT Pros Treat Licenses Like Investments

The Hidden ROI of Licensing Strategy

Modern IT decision-makers aren’t just buying software—they’re managing a digital portfolio. The wrong licensing model can:

  • Drain budgets through unnecessary renewals
  • Create compliance gaps
  • Lock teams into restrictive ecosystems

Smart licensing means:

  • Evaluating perpetual vs. subscription models
  • Leveraging license downgrade rights
  • Maximizing reusability and resale

Example: Microsoft Office 2019 vs. Microsoft 365

Perpetual licenses like Office 2019 still appeal to organizations wanting:

  • No recurring fees
  • Offline access
  • Long-term stability

Meanwhile, Microsoft 365 is preferred for:

  • Cloud integration
  • Constant updates
  • Scalable pricing

Choosing depends on operational needs, not marketing trends.


Key Takeaways: Software Strategy Is Asset Strategy

  • Microsoft licenses, much like crypto, represent digital value with real-world consequences.
  • Treat licensing as a strategic IT function—not just an admin task.
  • Understand the resale value, legal boundaries, and ROI of each license type.

For organizations aiming to stay efficient, compliant, and future-ready, licensing deserves a seat at the strategic table.

Not exactly the same—but for more such exciting content, visit softwarelicenses.net.

Why are Microsoft licenses getting more expensive?

Microsoft is pushing cloud-based subscriptions and reducing support for perpetual licenses. As a result, demand for older licenses has surged, especially in sectors where cloud isn’t feasible.

Can I resell unused Microsoft licenses?

Yes—under EU law and in certain other jurisdictions, resale of used software licenses is legal as long as the original copy is deleted. Always check compliance regulations.

What’s the difference between volume licensing and retail licensing?

Volume licensing is designed for businesses needing multiple seats and includes downgrade rights and bulk management features.
Retail licensing is for individuals or small setups, usually with higher per-license costs and fewer enterprise benefits.