How to use it: Check every statement that is true of your environment today. Be honest rather than optimistic — this is a tool for you, not a scorecard for anyone else. The more boxes you check, the more urgent your modernization case, and the more this assessment has already done your first draft for you.

Licensing & Cost Pressure

The status quo is rarely free. These are the signals that your Microsoft estate has become a financial risk rather than a stable line item.

Our SQL Server or Windows Server licensing costs have risen at the last one or two renewals, regardless of actual usage. We cannot confidently forecast what our Microsoft estate will cost over the next two renewal cycles. An Enterprise Agreement renewal is approaching, and it is one of the larger line items we do not actively scrutinize. A hardware refresh is on the horizon, and component prices are flat or rising rather than falling.

Technical Debt & Platform Risk

Working today is not the same as sustainable over any horizon that matters. These items surface debt that is easy to ignore until it forces a decision.

We run .NET Framework applications that are difficult to maintain and harder to staff. One or more Windows Server versions in our environment are approaching, at, or past end of support. We are not fully confident we have mapped every dependency between our core applications. A previous upgrade or migration surfaced hidden complexity we did not anticipate.

Capability & Capacity

The skills modernization requires are the ones the whole market is fighting to hire. These signals point to a capability gap that hiring alone will not close.

A meaningful share of our team's time goes to patching, maintenance, and firefighting rather than new work. We would struggle to hire cloud architecture, security, or migration skills on the timeline we need them. Business initiatives are waiting on infrastructure capacity or capability we cannot currently provide. Leadership is asking for AI results our current infrastructure cannot yet support.

Risk & Operational Exposure

An unplanned failure on aging infrastructure is uncontrolled risk on someone else's timeline. These are the exposures a structured modernization is designed to remove.

If our next renewal arrived tomorrow with another significant increase, we would have to accept it rather than switch. Demonstrating compliance across our environment requires significant manual effort. Our disaster recovery times are measured in days, or we are not certain how long recovery would take. Our environment's resilience depends heavily on institutional knowledge held by a few people.

Readiness to Make the Case

The final gap is rarely technical. It is whether you can put a defensible case in front of leadership. These items test how ready that case is today.

We do not yet have a documented cost-of-doing-nothing model we could show a CFO. We could not currently frame modernization as a business-risk decision rather than a technology preference. We have not identified external funding that could offset the cost of an assessment or first phase. We have no current-state assessment we could hand to leadership as evidence.

0 / 20 signals present

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Work through the five areas above. Your readiness picture builds as you go.

Your Next Step

Turn these signals into your own numbers.

Every box you checked is a line in the business case this assessment exists to help you build. A funded Opti9 modernization assessment turns these signals into your environment's real current state: a dependency map, a cost model with your figures in it, and a phased roadmap your leadership can approve one small door at a time.

Request your funded assessment → Prefer to read first? This assessment is the companion to the Opti9 + AWS ebook Make the Case for Modernization.