Migrations don't fail during the migration. They fail during the planning that didn't happen, and the failure just waits for cutover weekend to introduce itself. This is the checklist we run before moving anything. Every item exists because skipping it once cost somebody real money.
1. Inventory what you actually run
Every application, every server, every scheduled task nobody remembers writing. Include the invisible ones: the label printer's helper app, the macro-laden spreadsheet that pulls from the server, the service that faxes (yes, still) from the front desk. The half-forgotten stuff is precisely what breaks, because it's precisely what nobody planned for.
2. Map the dependencies
For each item: what does it talk to, and what talks to it? The accounting app reads the SQL database, the shipping tool reads the accounting app, the owner's Access report reads all three. Dependencies decide migration order, and undiscovered ones decide which week gets ruined. This map is also where you learn which systems must move together.
3. Reality-check your bandwidth
Cloud-everything turns your internet line into your backbone. Two questions: is it fast enough for the daily workload once files and apps live remote, and is the initial data upload even feasible? Two terabytes over a 20 Mbps upload is a nine-day upload, before anyone else uses the connection. Sometimes the answer is a bandwidth upgrade first, sometimes a seeded transfer, sometimes keeping the big-file workload local. And once the business depends on the line, failover internet stops being optional.
4. Check the licensing fine print
Some software licenses don't permit cloud hosting, some charge differently there, and some vendors support their app in the cloud only grudgingly with a support contract asterisk. Call each line-of-business vendor before committing. "Can I run your product on a cloud VM, supported?" is a five-minute call that has saved us from multi-week reversals.
5. Sort identity out first
Where do accounts and passwords live after the move? If the answer today is the aging domain controller in the closet, the answer tomorrow is probably Entra ID or Google identity, and that move wants to happen before the workloads, not after. Get SSO and MFA standing first; every subsequent step authenticates against it. Related decision: whether you still need Active Directory at all.
6. Note the compliance boundaries
Handling patient data, card data, or contractual data-residency promises? Providers offer compliant configurations (HIPAA BAAs, PCI-scoped setups), but compliance is in the configuration, not the logo. Know which rules apply before choosing regions and services, because retrofitting compliance is the expensive direction.
7. Write the rollback plan
For each phase: how do you back out if it goes sideways? Keep the old system intact and reachable until the new one has survived a real week, which is why parallel running is in the budget. A migration with no rollback plan isn't brave. It's just a bet with your payroll.
Checklist clean? Then sequence the actual move. That's what to move first.
Want this handled instead of homeworked? That's the job.
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