If You Are Rebuilding Your Microsoft AD or Entra ID Environment, Start With the Right Questions.
In today’s hybrid IT environments, identity is everything. Whether enabling secure access to cloud applications, enforcing compliance mandates, or controlling privileged accounts, your Microsoft Active Directory (AD) and Entra ID infrastructure forms the backbone of your enterprise’s cybersecurity posture.
But if your environment was designed for a different era, or if you’ve outgrown it without a clear roadmap, you’re not alone.
At AIS Network, we help large enterprises and government agencies modernize, secure, and streamline their Microsoft AD and Entra ID environments. As the AD services provider to the Commonwealth of Virginia, we help manage identity for over 65,000 state employees and contractors. That scale gives us a front-row seat to both the challenges and best practices in identity transformation.
Our advice? Before you start changing domain controllers, tweaking GPOs, or syncing new tenants, slow down and assess your foundation. The right questions will uncover hidden risks, clarify priorities, and reveal opportunities to align identity strategy with business goals.
Why Start With an Active Directory/Entra ID Strategic Assessment?
Identity environments evolve over time—and not always in intentional ways. Mergers, new cloud apps, shifting compliance standards, and growing technical debt can all lead to complex, fragile, or outdated AD/Entra setups.
A strategic assessment isn’t about listing every policy or user account. It’s about understanding how your identity environment serves your business and where it’s holding you back.
Below are select questions from our enterprise-grade AD/Entra ID assessment framework. These represent just a portion of the discovery process that we conduct with clients seeking clarity, modernization, and resilience.
Key Questions Every Organization Should Be Asking
Use this checklist to evaluate your Microsoft AD and Entra ID environment before making changes. Answering these questions helps uncover risks, clarify priorities, and align identity strategy with business goals.
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Identity footprint
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✅ How many organizational units (OUs), forests, and domains do you manage—and why?
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✅ Do these reflect your current business needs or outdated legacy structures?
These questions reveal whether your structure reflects your current business or a legacy of decisions past.
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Domain controllers
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✅ Are all domain controllers running supported OS and hardware?
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✅ Do you have a lifecycle plan or refresh strategy in place?
Without a clear inventory and modernization plan, domain controllers can quietly become your weakest link.
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Entra ID integration
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✅ Is your environment hybrid or cloud-native?
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✅ Are sync methods (AD Connect, Entra Cloud Sync) consistent and intentional?
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✅ Do you know how many Entra tenants exist—and why?
Hybrid identity demands intentional configuration. Too often, we find uncoordinated sync methods and duplicate objects creating security and management headaches.
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Privileged access governance
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✅ How are administrative accounts managed?
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✅ Is Role-Based Access Control (RBAC) centralized?
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✅ Is Multi-Factor Authentication (MFA) enforced across privileged and standard accounts?
Over-permissioned accounts and lax controls are consistently exploited in breaches. Strong governance is non-negotiable.
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Applications & integrations
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✅ Which apps (on-prem and cloud) rely on AD/Entra ID?
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✅ Are federated protocols (SAML, OAuth2, OpenID Connect) in place?
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✅ Could legacy apps break if sync models change?
Application dependencies often derail AD projects. An accurate integration inventory avoids disruption.
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Backup & recovery
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✅ Are domain controllers backed up regularly?
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✅ Have restore processes been tested recently?
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✅ Do you maintain documented runbooks/playbooks for recovery?
An identity outage doesn’t just impact IT. It brings the entire organization to a standstill.
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Tools & visibility
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✅ Do you have architectural diagrams, policies, and procedures available?
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✅ Are discovery tools (ADRecon, BloodHound, Quest, etc.) approved for use?
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✅ Will assessors have access to logs, domain controllers, and Azure portal?
Even the best intentions can stall without proper visibility and access.
What Comes After the AD/Entra ID Assessment Questions?
Only some of our questions are represented here. The answers to these questions and many others help us construct a clear, prioritized roadmap. For some clients, the result is a streamlined, better-secured hybrid identity environment. For others, it’s a complete redesign that consolidates domains, modernizes sync strategies, and automates governance at scale.
In every case, we provide practical, actionable guidance—not vendor fluff.
Why Choose AISN for Active Directory & Entra ID Transformation?
We were founded in 1993, and so, we have spent more than 32 years helping clients solve complex infrastructure and cybersecurity problems. As a trusted partner to the Commonwealth of Virginia, AIS Network brings:
- Proven enterprise-scale AD experience across public sector and regulated industries
- Deep Entra ID and Azure AD expertise, including hybrid environments and B2B/B2C configurations
- Security-first methodology, informed by NIST, Zero Trust, and Microsoft’s security baselines
- Full-stack managed services, from assessment through remediation and ongoing administration
Our team isn’t just here to audit your environment. We’ll help you transform it.
Take the First Step Toward a Smarter Identity Future
Don’t wait for an audit finding, a ransomware event, or a failed migration to start asking the right questions. Let AIS Network help you understand your current state, uncover hidden risks, and chart a course toward a secure, scalable identity future. Contact us today, and we will guide you through the hard questions—and the smart answers.