Most cloud migrations fail in a predictable sequence. You scope the technical work, set a timeline, and start moving workloads. Then hidden dependencies surface mid-project, double-run costs explode, and the timeline stalls.
According to the Flexera 2026 State of the Cloud Report, understanding application dependencies is cited as the single biggest migration challenge (54%).
Here is how to fix the migration grind before moving a single workload:
- Assess before you commit: Map application dependencies, categorize workloads using the 6 Rs framework, and assign a clear owner to every workload.
- Sequence by risk, not speed: Start by retiring unnecessary workloads. Move isolated rehost workloads next to build confidence. Sequence refactor workloads by what depends on them.
- Define cutover criteria early: Set measurable performance thresholds, data integrity checks, and rollback conditions before starting parallel operation to avoid unnecessary double-run spend.
- Address internal resistance: Involve engineering teams early in categorization, provide clear answers on technology autonomy, and secure visible executive ownership.
Check out the full post for a deep dive into the 4-phase migration playbook and practical cutover strategies:
Cloud migration playbook: escape lock-in | Upsun
A phased cloud migration playbook to escape vendor lock-in without disrupting delivery. Assess before you move, sequence by risk, and cut over with confidence
upsun.com
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