What Microsoft Customers Want From Microsoft in 2026: Stop Pushing and Start Proving Value

Microsoft is heading into 2026 with a massive footprint in the enterprise industry. But with that dominance comes a growing frustration from customers who feel like Microsoft has stopped listening and started assuming.

After spending time talking with CIOs and line-of-business leaders, one message keeps coming through loud and clear: Microsoft needs to stop acting like they’ve already earned the next “yes.”

Microsoft customers aren’t asking for perfection. They’re asking for respect, value, and a customer-first approach. Here is what customers actually want from Microsoft in 2026.

1) Stop Being Comfortable

Customers are tired of feeling like Microsoft is approaching them from a position of comfort. The perception is that Microsoft assumes customers can’t or won’t move away, so the company keeps pushing what it wants to sell next instead of focusing on what customers actually need.

This shows up in renewal conversations, licensing strategy, and the constant push toward “the next tier up,” regardless of fit.

2) Stop Forcing E5 When Customers Bought E3 for a Reason

If you’re a Microsoft 365 E3 customer, you’ve probably lived this scenario: you renew and the proposal includes E5, even when you’ve made it clear you don’t want it or need it.

What frustrates customers isn’t just the offer itself. It’s the tone behind it. Too often, the renewal is framed like, “Here’s why you should upgrade,” and then the “as-is” option is made to look intentionally painful.

Customers want proposals that reflect what they’ve already communicated, not a recycled upsell strategy.

3) Stop Jamming Copilot into Every Conversation

Copilot is a great example of something customers want to explore, but don’t want forced on them. Many organizations have started pilots or made early commitments, even at $30 per user. But the frustration builds when Microsoft immediately pushes for a massive expansion before customers feel they’ve validated the value.

Customers are saying: we’re still learning. We’re still testing. We’re not ready to jump from a few hundred users to thousands just because the pricing model rewards a bigger commitment.

They want Microsoft to slow down, support real adoption, and stop treating “scale” as the only success metric.

4) Stop Turning Azure Commitments into a Forecasting Trap

Azure is another major pain point. Customers don’t like being pushed into monetary commitments based on forecasts that stretch years into the future. It feels like they’re being asked to commit to spend they haven’t proven they need, simply because that’s the only way to unlock concessions.

Instead of “commit more so we can discount,” customers want Microsoft to show up with flexibility and value first, then earn the right to ask for deeper commitment.

5) Customers Aren’t Stupid. They See Microsoft’s Tactics

This is where trust starts to break down. Customers understand the difference between value-based selling and behavior-forcing tactics. Many feel Microsoft hasn’t actually proven the value of certain upgrades or add-ons yet but is still trying to push them through commercial pressure.

Here are a few examples customers notice immediately:

• Removing or reducing volume discounting to make staying put more expensive
• Announcing price increases tied to timing pressure (often conveniently aligned with Microsoft’s year-end)
• Bundling previously separate products into higher tiers to justify price hikes
• Making point solutions harder to buy independently so E5 becomes the “default path”

When customers experience these moves repeatedly, they stop hearing “innovation” and start hearing “forced behavior.”

6) Bundling and Consumption Pricing is Making Customers More Anxious

Customers are also wary of the growing trend of mixing subscription licensing with consumption-based charges inside the same bundle. The concern isn’t just cost; it’s uncertainty.

If an organization pays per user for E5, but then a bundled product becomes consumption-based, customers feel like they’re signing up for an unknown bill. Even worse, they don’t always trust that they’ll get clear transparency into what’s being consumed, how it’s measured, and how to control it.

From the customer’s perspective, successful adoption shouldn’t come with financial penalties they can’t predict.

The Opportunity: Small Changes Could Land Big

The good news for Microsoft is that customers aren’t saying “we’re done.” They’re saying “we’ll do more if you earn it.”

That path forward doesn’t require a reinvention. It requires a mindset shift:

• Lead with value
• Listen more than you pitch
• Stop using pricing pain as a strategy
• Help customers maximize what they already own
• Bring proposals that reflect real needs, not default upsell motions

Even small changes would land well because right now, the perception is what it is.

The Bottom Line

Microsoft customers want a different relationship in 2026. Not one driven by forced upgrades, bundling pressure, artificial deadlines, and commitments based on hypothetical future spend.

They want Microsoft to take a step back, prove value, and act like a partner again.

If you’re looking to take control of your Microsoft strategy in 2026, UpperEdge’s Microsoft Advisory Practice can help you validate value, reduce commercial risk, and negotiate from a position of strength. See how our advisory services can help you gain Microsoft negotiation leverage here.