For years, the Microsoft cost conversation started and ended with licensing. You renewed, or you didn’t. It was, in the words of TrustedTech Senior Director of Professional Services Heath Madison, a simple story: “It’s time to renew, I renewed, or even before that, it’s a perpetual license, I buy the license, and I’m done.” That story doesn’t hold up anymore.
Every Microsoft license now sits on top of a stack of other decisions: security controls, compliance requirements, AI governance, and whether anyone is actually using what you bought. During a recent TrustedTech webinar on Microsoft cost strategy, Madison and two of the firm’s program leads, Jason Lou and Tim Woringer, walked through why the price on the invoice is only part of what organizations are actually paying, and where the real savings and risk sit instead.
This post breaks down what they covered: the July 2026 licensing changes, where hidden Microsoft costs actually accumulate, and what proactive support looks like when it’s built around optimization rather than just fixing what’s broken.
The July 2026 Price Changes: What You’re Actually Paying For
Starting July 1, list prices on Microsoft’s core E3 and E5 bundles increased. On its own, that sounds like a straightforward cost hike. But as Madison explained, the increase came bundled with meaningfully more product.
E3 is picking up Intune Remote Help, advanced analytics, and Defender for Office, features that would cost roughly $14.50 a month if purchased separately. The bundle price is going up $3. E5 adds Security Copilot and the full Intune suite, worth about $11.60, for the same $3 increase. E7 goes further still: full Copilot licenses, Agent 365, and the complete Entra suite stack on top of everything in the new E5, adding roughly $57 in separately priced value for an incremental $99.
“If we just focus on that $3 increase, yes, it’s more expensive,” Madison said. “If we look at the value, you have a lot more value.” The catch, and it’s a real one, is that the value only shows up if the organization actually deploys and adopts the new capabilities. A price increase attached to features nobody turns on is just a price increase.
The Iceberg Problem: Where Microsoft Costs Actually Hide
This is the part of the webinar Madison spent the most time on, because it’s the part most organizations get wrong. “People just assume it’s because the licensing price went up,” he said. “But a lot of those biggest increases are really tied more to unmanaged growth. It’s not the price itself.”
He used a simple image: the license cost is the tip of the iceberg, the part you see above water. Below the waterline sits underutilized licenses, Azure sprawl, and poor governance, and that’s where the real cost lives. The distinction that matters operationally is timing. “When it comes to the licensing price, you negotiate that once a year, but that other stuff below the line, that’s compounded daily. Getting in front of it is key.”
Madison shared a concrete example from a licensing engagement with a large enterprise customer: TrustedTech’s review found the organization was overspending by $1.2 million, largely because of licenses purchased at a tier the users didn’t need. As he put it, “the person working on your plant floor doesn’t need the same license as finance, sales, or marketing. They just interact with technology differently.” Not every organization will find seven figures of waste, but the pattern he described, buying one license tier for an entire org regardless of role, is common, and it compounds every time a contract auto-renews without review.
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Grow, Upgrade, or Optimize: A Framework for Renewal Decisions
TrustedTech’s team frames every renewal decision around three questions: does the organization need to grow (user count increasing), upgrade (current licenses no longer match user or organizational needs), or optimize (right-sizing what’s already been purchased)?
Optimize is where Lou and Madison said most of the missed value sits, and it’s also the least visible of the three, because it doesn’t show up as a line item the way growth or upgrades do. Optimization touches licensing waste in two specific forms: overlicensing, where an organization pays for capabilities it never uses, and misaligned licenses, where a team lacks a capability it actually needs, like Purview-based data classification for HR, because it wasn’t included in their license SKU. Both problems get carried forward automatically the moment someone clicks renew without reviewing usage first.
Support Beyond the Ticket
Tim Woringer, who works directly with TrustedTech’s certified support customers, made the case that support quality isn’t just about how fast a ticket gets closed. It’s about how much gets resolved without ever leaving the organization’s own support team.
“There is unlimited resolution in-house at TrustedTech,” Woringer said. “The beautiful thing about that is the fact that we solve nearly 86% of tickets in-house, just because of the investments that we’ve made on the engineering team.” For the cases that do need to go further, TrustedTech holds a Premier Support for Partners contract with Microsoft, which includes severity-A escalation paths and access to an incident management team, for both cloud and on-premises or hybrid environments.
The proactive side of that support model breaks into three pieces: consulting sessions for strategic questions (Woringer described these as ranging from security-focused conversations to pre-migration sanity checks), professional services for hands-on project work like deployments and assessments, and a Designated Technology Advisor who works as an ongoing extension of the internal IT team rather than a per-ticket resource.
Why AI and Security Readiness Can’t Be an Afterthought
Woringer was direct about the risk math changing as organizations adopt more AI: “AI really changes the risk equation. It not only amplifies productivity, but it also can amplify any security gaps that you may already have.” A misconfigured identity or an over-permissioned account is a gap either way. Add Copilot on top of ungoverned data access, and that gap has a much larger blast radius.
Before rolling out Copilot or moving to E7, TrustedTech’s assessments evaluate five specific readiness pillars: identity, security, data governance, user adoption, and compliance. The output isn’t just a list of problems. It includes a tenant overview, a secure score benchmark, and a prioritized roadmap covering the full Microsoft 365 stack, not just Entra or Purview in isolation, so the organization has both the current state and a sequence for fixing it.
Designated Technology Advisor vs. Trusted Advisor
Lou described these two programs as working in parallel rather than as alternatives, comparing them to “Batman and Robin.” The Designated Technology Advisor (DTA) is a generalist, a named engineer who’s present on every ticket an organization opens and who builds a working understanding of the environment over time. That person’s job isn’t just to spot fires; it’s to flag where a licensing tier doesn’t match usage, where governance is missing, and where a specialist should get pulled in.
That’s where the Trusted Advisor track comes in. It’s specialized by product area, and for organizations running Azure, it covers three workstreams: FinOps, SecOps, and governance. Lou put the underlying question plainly: “Am I doing this with best practices in mind? Did I inherit something from people who may have left the organization?” For environments that have been running for years without a fresh set of eyes, that’s often exactly the gap.
TrustedTech vs. Microsoft Unified Support: What’s the Real Difference
This question comes up often enough that Lou addressed it directly during the webinar’s Q&A. Functionally, both paths connect to the same Microsoft escalation channels and the same Premier-tier engineering access. The difference is what happens before an issue reaches Microsoft at all.
“Where you really shine with what we can deliver is the 86% of the time that we get to resolve the tickets in-house,” Madison said. “This way, there’s full control and full partnership with us and you on that 86-plus percent of the time.” He also noted that most support delivered under a Unified contract is itself handled by third parties, since Microsoft doesn’t staff every support tier internally. The real distinction, in other words, isn’t Microsoft versus a partner. It’s which partner is doing the resolving, how much they can close without an escalation, and how invested they are in the outcome rather than the ticket count.
Frequently Asked Questions
Q. Does my support contract include free consulting?
A. Every paid CSS tier from Essentials through Enterprise includes some level of advisory time or professional services credit. Essentials and Standard include 15 and 30 hours, respectively; Commercial and Enterprise tiers include a Designated Technology Advisor. Unused entitlements are tracked, so it’s worth checking with your account manager before assuming you need to purchase additional hours.
Q. What does an M365 or Copilot readiness assessment cost?
A. It depends on your existing relationship with TrustedTech and current support tier, since professional services discounts scale with tier. Current customers should contact their account manager; new customers can request pricing directly through TrustedTech.
Q. Can TrustedTech take over support if I’m already mid-contract with another provider?
A. Yes. The transition process starts with understanding what’s currently open and what’s been resolved historically, so there are no gaps in coverage during onboarding. TrustedTech has managed this kind of mid-contract transition before and builds a transition plan before anything moves over.
Q. Is TrustedTech support better than going directly through Microsoft?
A. It depends on what “directly through Microsoft” means. Without a support contract, you’re limited to standard support levels. With a Unified contract, you’re often still working with a third-party delivery team behind the scenes. TrustedTech’s advantage is resolving roughly 86% of tickets in-house with dedicated engineers, plus access to Premier Support for Partners for anything that needs to be escalated further.
Q. Which support tier includes advisory sessions?
A. All paid tiers include some advisory access. Essentials and Standard come with a fixed number of advisory hours built into the package. Commercial and Enterprise tiers move beyond hours-based advisory into a Designated Technology Advisor, a named engineer who stays involved on an ongoing basis rather than being brought in per session.
Where This Leaves Your Microsoft Budget
The license price is the number everyone sees. It’s also the smallest lever in the equation. The bigger cost drivers and the bigger opportunities sit in whether licenses match actual usage, whether security and AI readiness were addressed before rollout, and whether support is built to catch problems before they become incidents.
If it’s been a while since your organization looked at licensing usage against actual assignments, or if Copilot and E7 are on the roadmap without a readiness assessment behind them, that’s the gap worth closing first. TrustedTech’s licensing consultation and M365 readiness assessment are built to surface exactly that: where the waste is, where the risk is, and what to prioritize first. Schedule a consultation with TrustedTech’s advisory team to see where your environment stands.
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- License right-sizing strategies
- SKU comparison and downgrades
- CSP vs. direct pricing analysis
- Governance and audit frameworks
- Copilot and add-on cost controls
- Renewal negotiation tactics
