The landscape nobody had inventoried
A landscape carried years of custom programs that everyone assumed had to migrate. The inventory found hard-coded values, duplicated logic and programs nobody had run in years. Half the "must migrate" list was retired instead, and the plan shrank with it.
The three systems that disagreed
Development, QA and production turned out to be configured differently in places nobody had noticed, which is why testing never caught certain production errors. The readiness check surfaced it, and aligning the three systems became the first step of the roadmap rather than a surprise in the middle of it.
The sandbox that answered the question
Finance feared the upgrade would break payment runs and asset transfers. A sandbox copy on the new release let them try both before the project was approved. Two issues were found and fixed in advance; the rest of the fear turned out to be unfounded.