Cloud Readiness Assessment: A Pre-Acquisition Framework for Cloud Migration Planning

Before you tell the acquired company “we’re moving everything to Azure,” run a cloud readiness assessment. Not every company’s technology estate is ready for cloud migration — and the cost of getting this wrong is significant.

The Cloud Migration Readiness Scorecard

Assess each dimension before committing to a cloud migration plan:

Score 13-15: Good candidate for cloud migration. Azure-recommended.

Score 8-12: Partial cloud migration viable. Hybrid cloud recommended initially.

Score 5-7: Significant work required before cloud migration is cost-effective.

Below 5: Cloud migration should be deferred 18-24 months. Focus on IT infrastructure modernization first.

Application Architecture Assessment

The 12-Factor App Test

Cloud-native applications are designed for cloud deployment. The 12 factors (Heroku’s methodology) are: codebase, dependencies, config, backing services, build/release/run, processes, port binding, concurrency, disposability, dev/prod parity, logs, admin processes.

For each major application, determine:

• Can this application run as a container? (Docker/OCI format)
• Does it store configuration in environment variables (not config files)?
• Does it use platform-as-a-service backing services (Azure SQL, Azure Cache for Redis) or can it be adapted?
• Does it follow stateless design (no local file storage for state)?

Applications that fail the 12-factor test and are tightly coupled to on-premises infrastructure (hard-coded on-prem database URLs, reliance on local file shares for state) require significant rework before cloud migration. This rework cost needs to be in the deal model.

The WVD/FSLogix Readiness Check

Windows Virtual Desktop (Azure Virtual Desktop) is the standard for migrating user desktops to cloud. FSLogix is the profile management solution that makes AVD viable for enterprise desktop migration.

Check for the FSLogix readiness blockers:

• Do any of the acquired company’s applications store profile data in the user’s local AppData? (FSLogix redirects AppData, but some apps break)
• Are there apps that use hardware dongles or local COM objects that can’t be virtualized?
• Do the company’s compliance requirements mandate data residency in a specific geography? (AVD can accommodate this, but needs planning)
• What is the current profile size (Roaming Profile vs. FSLogix)? Profile sizes over 50GB cause login performance issues in AVD.

Data Estate Assessment

SQL Server Version Compatibility

Azure SQL Database (the PaaS version) supports SQL Server 2016 and above with some limitations. Azure SQL Managed Instance supports most SQL Server features including SQL Agent, linked servers, and cross-database queries.

The critical compatibility issue: SQL Server 2008 R2 and below cannot be migrated to Azure SQL Database without application changes. They must be migrated to Azure VMs (IaaS) running SQL Server, which has different cost and management implications.

For a typical mid-size company, the discovery finding that changes the cloud migration plan: discovering they have SQL Server 2008 R2 databases supporting business-critical applications. Those databases need to either be upgraded before cloud migration or moved to Azure VMs.

The Data Gravity Problem

Data gravity is the tendency of applications to gravitate toward their data. Once an application is moved to Azure, its database needs to be in Azure too (for performance). Moving large databases across regions or between on-prem and cloud is expensive and slow.

Assess: what is the total size of the data estate? What are the largest databases? What is the network bandwidth between the on-prem data center and Azure?

For databases over 10TB, the migration path is likely Azure Data Factory for ETL + Azure SQL or Cosmos DB — but the migration timeline for a 10TB database over a 1Gbps WAN link is 2-3 days minimum for a full cutover.

Identity Readiness

If the target company is not already using Azure AD (or is using it only for M365 without proper synchronization), cloud migration is significantly more complex.

The identity prerequisite for cloud migration:

• Azure AD Connect must be configured and validated for the source AD environment
• All user accounts must have a corresponding Azure AD identity (even if not licensed for M365)
• Service accounts must be validated in Azure AD

If the target company has a messy AD environment (many orphaned accounts, no clear OU structure, complex trust relationships), the identity cleanup needs to happen before cloud migration begins. Identity cleanup is typically 3-6 months of work.

The Azure Arc Question

Azure Arc enables Azure management and policy for on-premises and edge environments. It’s relevant for companies that aren’t fully cloud-ready — they can use Arc to extend Azure’s governance and security tools to their on-prem estate while keeping workloads on-prem.

For M&A: if the acquired company has significant on-prem infrastructure that can’t be migrated in the near term, Azure Arc provides a path to unified management without immediate migration. The Arc agent is a lightweight install that can be deployed to servers in days.

ACQI’s Azure discovery module identifies whether the target’s Azure environment has Arc configured and what the coverage is — giving the integration team a baseline for the cloud readiness assessment.

The Honest Timeline

A realistic cloud migration timeline for a mid-size company’s IT estate:

• Assessment and planning: 2-3 months
• Identity cleanup and preparation: 3-6 months (if significant AD debt exists)
• Application portfolio rationalization: 2-3 months (which apps to migrate, retire, or replace)
• Pilot migration (10-20 users): 1-2 months
• Wave-based user migration: 6-18 months depending on user count and app count
• Legacy decommission: 3-6 months post-migration

Total: 18-36 months from deal close to fully cloud- migrated environment. Anything shorter than this is a heroic timeline that will compromise quality or user experience.