Beginning July 1, 2026 Microsoft will increase pricing across several commercial plans: Office 365 E3, Microsoft 365 E3, Microsoft 365 E5, frontline licensing, and business plans. Microsoft attributes the increases to expanded capabilities tied to AI integration, security tooling, Intune management,…
When Your SAM Lead Is Out, Is Your Team Ready?
Vacation season exposes a SAM risk most enterprises never plan for. A vendor sent a True-Up request on a Tuesday. Moderate ask, tight window. The person who owned the software asset management position was in Costa Rica until the following Monday….
Microsoft Copilot ROI Reality Check: Why Enterprises Are Backing Out.
Over the past several months, I’ve had the same conversation with multiple large organizations. They adopted Microsoft Copilot with genuine enthusiasm, assigned licenses, ran internal communications, and waited for productivity gains to show up. For most of them, the gains never…
AI Spend Governance Starts With Token Consumption.
Real life scenario: a $500,000 charge landed on an invoice from a single query run without guardrails. The team had no visibility until after the fact. The vendor refunded most of it, but not all. This story came up in three…
When “More Licenses” Creates More Microsoft Compliance Risk.
A company discovers gaps in its Microsoft licensing position, so the response feels obvious: Buy more CALs. Usually Device CALs. Sometimes User CALs. Often far more than the environment appears to require. The assumption is simple: if the organization owns more…
Microsoft EA Renewal Negotiation: The 30-Year Playbook.
I spent 8 years inside Microsoft selling the Enterprise Agreement before I started helping clients negotiate against it. The Microsoft EA renewal negotiation playbook has not changed in 30 years. Every renewal walks into the same machine. Most clients do not…
Your Microsoft EA Proposal Has a Math Problem.
A mid-size enterprise received two Microsoft EA proposals at renewal. One was built around Microsoft 365 E3, the other around Microsoft 365 E5. The M365 E5 package was quoted at roughly $8M per year. The M365 E3 package came in at…
Microsoft EA True-Up: Why Finance Called It a Budget Miss.
A large enterprise signed a three-year Microsoft EA for $6 million per year, with a purchase order totalling $18 million to cover the full term. Within the first 90 days, they restructured their license mix, adding $2 million per year to…
The Azure Agreement Terms That Aren’t in Your Contract.
A mid-market technology company was three months out from an Azure commitment renewal when its procurement team sat down to build a negotiation position. They pulled up the signed agreement. They reviewed the statements of work. They put together a summary…
Microsoft EA Renewals: The Baseline Pricing Level.
Three client conversations in a single week. Three different organizations, different sizes, different industries. One pattern that showed up in all of them. Microsoft presented a renewal proposal. The discount line didn’t look like it used to. In one conversation, Microsoft…