Cloud Readiness Checklist

Moving to the cloud is one of the most impactful decisions a business can make, but rushing in without preparation leads to cost overruns, security gaps, and frustrated teams. This checklist covers six critical areas you need to evaluate before starting any cloud migration project.

1. Current Infrastructure Assessment

Before you can plan where you are going, you need a complete picture of where you are today.

• ☐ Documented all physical and virtual servers, including their roles, operating systems, and resource utilization
• ☐ Inventoried all business applications, noting which are on-premises, SaaS, or hybrid
• ☐ Identified dependencies between applications and services (which systems talk to each other)
• ☐ Cataloged all databases, their sizes, growth rates, and performance requirements
• ☐ Mapped current storage usage, including file shares, archives, and backups
• ☐ Documented licensing for all software, noting which licenses transfer to the cloud and which do not

2. Network and Bandwidth

Cloud performance depends heavily on your internet connectivity. Bandwidth that feels fine for web browsing may not hold up when your entire workforce is accessing cloud-hosted applications and files.

• ☐ Measured current internet bandwidth (upload and download) at each office location
• ☐ Estimated bandwidth requirements for cloud workloads (VDI, SaaS apps, backups, VoIP)
• ☐ Verified ISP can provide sufficient bandwidth and reviewed SLA commitments
• ☐ Evaluated whether a dedicated connection (Direct Connect, ExpressRoute) is needed for latency-sensitive workloads
• ☐ Tested current latency to target cloud regions from each office location
• ☐ Planned for redundant internet connections to avoid a single point of failure

3. Security Posture

Cloud migration does not eliminate security responsibilities. It shifts them. You need to understand the shared responsibility model and ensure your security practices are ready for a cloud environment.

• ☐ Reviewed current firewall rules and determined how they translate to cloud security groups
• ☐ Confirmed Multi-Factor Authentication (MFA) is enabled for all administrative accounts
• ☐ Evaluated identity management strategy (Active Directory sync, Azure AD, AWS IAM)
• ☐ Documented current encryption practices for data at rest and data in transit
• ☐ Reviewed compliance requirements (HIPAA, PCI-DSS, SOC 2) that affect cloud architecture decisions
• ☐ Identified which security tools need to be replaced or supplemented for cloud environments
• ☐ Verified that logging and monitoring capabilities extend into cloud workloads

4. Application Compatibility

Not every application is cloud-ready. Some will migrate easily, others will need modification, and a few may need to stay on-premises or be replaced entirely.

• ☐ Categorized each application: lift-and-shift, refactor, replace with SaaS, or retain on-premises
• ☐ Tested critical applications in a cloud staging environment before committing
• ☐ Identified applications with hardware dependencies (USB dongles, local printers, specialized peripherals)
• ☐ Checked vendor support policies for running their software in cloud environments
• ☐ Evaluated legacy applications that may require older operating systems or runtimes
• ☐ Assessed latency sensitivity for applications that require real-time responsiveness

5. Data Classification

Understanding what data you have, where it lives, and how sensitive it is determines your cloud architecture, storage tiers, and compliance obligations.

• ☐ Classified data by sensitivity level (public, internal, confidential, regulated)
• ☐ Identified all data subject to regulatory requirements (PHI, PII, financial records)
• ☐ Determined data residency requirements (does data need to stay in specific geographic regions)
• ☐ Estimated total data volume and identified data that can be archived or deleted before migration
• ☐ Planned data transfer method (online transfer, physical shipping for very large datasets)
• ☐ Documented data retention policies and how they will be enforced in the cloud

6. Staff Readiness

Technology changes succeed or fail based on people. Your team needs to understand what is changing, why, and how to work in the new environment.

• ☐ Assessed IT team skills and identified training needs for cloud administration
• ☐ Planned end-user training for new workflows (file access, application launching, VPN changes)
• ☐ Identified a project sponsor from leadership who will champion the migration
• ☐ Communicated the migration timeline and impact to all stakeholders
• ☐ Established a support plan for the transition period (extra help desk coverage, escalation paths)
• ☐ Documented rollback procedures in case critical issues arise during migration

If you checked most of these boxes, you are in a strong position to move forward with a cloud migration. If you found significant gaps, address them first. A few weeks of preparation can save months of troubleshooting after the fact.