Can AI Outperform Microsoft Licensing Specialists

AI tools are getting very good at answering complex technical questions, including software licensing. But how close are they to matching the depth, nuance, and risk awareness of a specialist who spends all day inside Microsoft contracts and product terms?

To find out, we put four leading AI tools to the test on a set of Microsoft specific licensing questions:

• Claude Sonnet 4.5
• OpenAI GPT-5 (ChatGPT)
• Gemini Pro
• Copilot GPT-5

Each AI received the same four questions about Windows Server, RDS, and Conditional Access licensing. Responses were scored on accuracy, completeness, and practical usefulness from the perspective of real-world enterprise scenarios.

Below is how they performed.

Microsoft Licensing Results (Round 1)

Copilot GPT-5 came out on top in this Microsoft-specific round, but all four tools delivered usable answers with varying levels of nuance and practical guidance.

Below is the full breakdown by question.

OpenAI GPT-5

1) How do I license Microsoft Windows Server?

A. License the server software
• Core based licensing (Windows Server Standard & Datacenter). You must license all physical cores in the host, with minimums of 16 cores per server and 8 cores per physical processor. Standard is for low/medium virtualization; Datacenter is for high density.
B. License access to the server
• Every internal user/device that connects needs a Windows Server CAL (User or Device). External users can be covered per server with an External Connector instead of individual CALs.
C. Virtualization rights (most asked detail)
• Standard: licensing all cores on the host grants rights for up to 2 Windows Server VMs (plus the host for Hyper V). To run more, you stack another full set of core licenses for each additional pair of VMs.
• Datacenter: licensing all cores grants unlimited Windows Server VMs on that host.
D. Per VM licensing (introduced Oct 2022)
• If you have Software Assurance (SA) or a subscription license, you may license by individual virtual machine instead of by the physical host. Each VM is licensed by its vCPU count (minimum 8 cores per VM; program rules include additional minima), giving flexibility on large hosts.
E. In Azure (IaaS) specifics
• When you deploy Windows Server from the Azure gallery (license included), Windows Server CALs are not required to access that VM—those rights are included in the VM price. (This exception is Azure only.)

2) Are there other licensing methods beyond “on the hardware”?

Yes—four common options:

1. Per VM licensing (on prem)
   o Available only with SA or subscription; license each VM by vCPU (min 8 per VM). Useful on large hosts with few Windows VMs.
2. Azure Hybrid Benefit (AHB)
   o Apply existing Windows Server licenses with SA/subscription to Azure to pay the Linux (base compute) rate for VMs. Great for cost optimization or lift and shift.
3. Outsourcing / Authorized Outsourcer
   o Microsoft allows use of your licenses at eligible third party datacenters under the outsourcing terms (post 2022 policy). Read the official outsourcing guidance to see what is and isn’t allowed with SA/subscription.
4. Service Provider models (SPLA)
   o For hosters to provide licensed services on a monthly, usage basis (customer “rents” the rights). Not a typical enterprise buy, but important in hosted scenarios. (Always check current provider eligibility vs. Listed Providers policy.)

3) Do I need Software Assurance for my RDS CALs in an onprem environment?

Short answer: No, SA is not required for purely on premises RDS.
• On prem, you must buy RDS CALs (User or Device) in addition to Windows Server CALs; SA is optional, but gives upgrade/mobility benefits.

When SA is required or highly valuable
• Using RDS against a Windows Server hosted in Azure or another provider: You need RDS User CALs with active SA (or RDS User subscription) to exercise the RDS Extended Rights for hosted/shared environments.
• Version agility & rights: SA grants version upgrade rights and other benefits; without SA, you must align CAL version to the server version.

Note: The “no CALs needed in Azure” exception does not apply to RDS. Azure includes base Windows access rights, but RDS still requires RDS CALs (with SA for hosted/shared).

4) I want to enable all Conditional Access — what license do I need?

Baseline rule:
• Custom Conditional Access policies require Microsoft Entra ID P1 (formerly Azure AD Premium P1).
• Risk based Conditional Access (leveraging Entra ID Protection) requires Microsoft Entra ID P2.

“All Conditional Access” in practice = include risk based policies → choose P2.
• If you intend to use user/sign in risk conditions, automated risk remediation, and Identity Protection, that’s P2.

Assignment principle (compliance):
• Licenses must be assigned to every user who benefits from the feature (not just admins). If a user is in scope of a CA policy, that user needs the appropriate P1/P2 license.

Bundles that include the right SKU
• Microsoft 365 E3 includes Entra ID P1.
• Microsoft 365 E5 includes Entra ID P2

Claude Sonnet 4.5

1. How do I license Microsoft Windows Server?

Windows Server 2025 Standard and Datacenter editions are licensed under a core-based license model. Here are the main methods:

Core-Based Licensing (Physical Cores):
• The number of core licenses required equals the number of physical cores on the server, subject to a minimum of 8 core licenses per physical processor and a minimum of 16 core licenses per server
• Core licenses are sold in 2-packs and 16-packs

Editions:
• Standard Edition: Allows running 2 virtual machines (VMs)
• Datacenter Edition: Allows unlimited VMs on the licensed server

Pricing: For Windows Server 2025 Datacenter edition, the list price is $6,771 and covers a 16-core CPU

2. Are there any other licensing methods other than on hardware level?

Yes! There are now additional licensing options:

Virtual Machine-Based Licensing: Licensing by virtual machine is available only under subscription licenses or licenses with active Software Assurance. For each server licensed by virtual machine, the number of core licenses required equals the number of virtual cores in a virtual operating system environment, subject to a minimum of 8 core licenses per virtual machine.

Pay-As-You-Go (PAYG) Model: Windows Server 2025 PAYG is a subscription-based licensing option that works with the Azure Arc management tool. Key features:
• Microsoft charges Windows Server PAYG per CPU-core-hour at a fixed Azure rate of $33.58 per core, per month, which breaks down to about $0.046 per core, per hour
• Windows Server workloads require Client Access Licenses, but PAYG does not, although Remote Desktop Services, or RDS, CALS are still needed
• Requires Azure Arc and internet connectivity

3. Do I need Software Assurance for my RDS CALs when I have an on-premise environment?

For on-premise only deployments: NO
On-premises deployments do not require SA – you can use perpetual CALs as long as you stick to the licensed server version, though you’ll need to purchase new CALs when you eventually move to a newer Windows Server OS.

However, you DO need Software Assurance if:
• You have RDS User CALs with active Software Assurance, you may use them simultaneously on-premises and in Azure
• You want license mobility to cloud environments
• RDS CALs without SA, or Device CALs, cannot be used for Azure sessions

4. I want to enable all conditional access – what license do I need?

Required License: Microsoft Entra ID Premium P1 (or higher)
Conditional Access is a per-user licensed feature. Any user who is directly or indirectly governed by a Conditional Access policy must have a Microsoft Entra ID P1 (or higher) license assigned.

Important Details:
• Using this feature requires Microsoft Entra ID P1 licenses
• While Conditional Access technically enables at the tenant level with just one P1 license, compliance requires that every user benefiting from the feature be licensed
• If a user is not targeted by any Conditional Access policy (and doesn’t indirectly benefit), they do not need a P1 license

Licenses that include Conditional Access:
• Microsoft Entra ID Premium P1 or P2
• Microsoft 365 Business Premium
• Enterprise Mobility + Security (EM+S) E3 or E5
• Microsoft 365 E3 or E5

For advanced risk-based conditional access policies, you’ll need Microsoft Entra ID Premium P2.

Gemini Pro

1. How do I license Microsoft Windows Server?

For the current versions of Windows Server (e.g., 2022, 2019), the primary licensing model for the Standard and Datacenter editions is per-core.

Here is a breakdown of the rules:
• Core-Based Licensing: You must license all the physical processor cores in the server.
o Minimum per Processor: You must license a minimum of 8 cores for each physical processor.
o Minimum per Server: You must license a minimum of 16 cores for each physical server.
o (Even if you have a single 4-core processor, you must buy 16 core licenses. If you have a single 12-core processor, you must still buy 16 core licenses. If you have two 10-core processors, you must buy 20 core licenses.)

• Client Access Licenses (CALs): In addition to the server core licenses, you must also purchase a CAL for every user or device that will access the server.
o User CAL: One license for one user, allowing them to access the server from any number of devices.
o Device CAL: One license for one device, allowing any number of users to access the server from that specific device.

• Edition Differences (Virtualization):
o Windows Server Standard: When you have licensed all physical cores, this gives you the right to run two Windows Server virtual machines on that host.
o Windows Server Datacenter: When you have licensed all physical cores, this gives you the right to run unlimited Windows Server virtual machines on that host.

2. Are there any other licensing methods other than on hardware level?

Yes, there are.

• Subscription Licensing: You can license Windows Server on a subscription basis, commonly in Azure.
• Licensing by Virtual Machine:
o Only available with Software Assurance or subscription
o Must license all vCores, minimum 8
o Ideal for high-density hosts or third-party hosting

3. Do I need Software Assurance for my RDS CALs when I have an on-premise environment?

No, Software Assurance (SA) is not required for your on-premise RDS CALs to function.

Version Compatibility:
• Your RDS CALs must be for a version equal to or newer than your server.
• Without SA, upgrading servers means buying new CALs.
• With SA, you automatically gain rights to newer CALs.

4. I want to enable all conditional access what license do I need?

To enable “all” Conditional Access features, you need a Microsoft Entra ID Premium P2 license.

• P1 = core Conditional Access
• P2 = all risk-based features

Co-Pilot GPT-5

1. How do I license Microsoft Windows Server?

‍

Core-Based Licensing for the Server

• Windows Server Standard & Datacenter editions use a per-core licensing model.
• You must license all physical cores on the host machine:
  • Minimums:
    • 8 cores per processor
    • 16 cores per server
• Licenses are sold in 2-core packs.
• Edition choice matters:
  • Standard: Best for lightly virtualized or physical environments. Includes rights for up to 2 VMs per fully licensed server.
  • Datacenter: Designed for highly virtualized environments. Grants unlimited VMs on the licensed host.

Client Access Licenses (CALs)

• Every user or device connecting to the Windows Server requires a Windows Server CAL.
• Two CAL types:
  • User CAL: Ideal if users access from multiple devices.
  • Device CAL: Ideal if multiple users share the same device.
• For external users, you can use an External Connector license instead of individual CALs.
• Additional CALs (e.g., RDS CALs) are needed for Remote Desktop Services.

Virtualization Rights

• Standard Edition:
  • Licensing all cores allows 2 VMs + the host for Hyper-V.
  • To run more VMs, you stack additional core licenses.
• Datacenter Edition:
  • Licensing all cores grants unlimited VMs on that host.
• Per-VM Licensing (introduced Oct 2022):
  • Available with Software Assurance (SA) or subscription.
  • License each VM by its vCPU count (minimum 8 cores per VM).
  • Useful for large hosts with few Windows VMs

Cloud & Hybrid Scenarios

• Azure deployments:
  • When you use Windows Server images from the Azure gallery, CALs are included in the VM price.
• Azure Hybrid Benefit (AHB):
  • Apply existing Windows Server licenses with SA to Azure VMs to reduce costs.
• Pay-as-you-go:
  • Windows Server 2025 introduces a cloud billing option for on-prem servers via Azure Arc.

Essentials Edition

• For small businesses (up to 25 users, 50 devices).
• Simpler licensing—no CALs required.

Quick Decision Guide

• Few VMs or physical servers? → Standard Edition + CALs.
• Highly virtualized environment? → Datacenter Edition.
• Hybrid or Azure workloads? → Consider AHB or pay-as-you-go.

2. Are there any other licensing methods other than on hardware level?

Per-VM Licensing

• Instead of licensing all physical cores, you can license individual virtual machines.
• Requirements:
  • Available only with Software Assurance (SA) or subscription.
  • Each VM must be licensed for a minimum of 8 cores.
• Ideal for:
  • Large hosts running only a few Windows Server VMs.
• Benefit:
  • Reduces cost when you don’t need unlimited virtualisation rights.
    (Introduced October 2022)

Subscription-Based Licensing

• Offered through Microsoft CSP (Cloud Solution Provider) or Enterprise Agreement.
• You pay a monthly or annual subscription for Windows Server rather than buying perpetual licences.
• Often bundled with Azure Hybrid Benefit for hybrid scenarios.

Pay-As-You-Go via Azure Arc

• New model for Windows Server 2025:
  • Connect your on-prem servers to Azure Arc.
  • Pay for Windows Server usage on a metered basis, similar to cloud billing.
• Great for:
  • Organisations that want operational expenditure (OpEx) instead of capital expenditure (CapEx).

Azure Virtual Machines

• When you run Windows Server in Azure, licensing is included in the VM price.
• No need for separate CALs in Azure-hosted environments.

Essentials Edition

• For small businesses (up to 25 users, 50 devices).
• Simpler licensing—no CALs required

3. Do I need Software Assurance for my RDS CALs when I have an on-premise environment?

• No, SA is not required for day-to-day functionality of Remote Desktop Services (RDS) CALs on-premises.
  Your RDS CALs will work without SA as long as they match the version of the Windows Server OS on your RDS Session Host.
  • Example: You cannot use a 2019 RDS CAL to access a 2022 RDS Session Host.
  • You can use a 2022 RDS CAL to access 2022, 2019, or 2016 hosts.

What does Software Assurance provide?

• Upgrade Rights: If you upgrade your servers (e.g., from Windows Server 2019 to 2022), SA allows you to upgrade your existing RDS CALs without buying new ones.
• Without SA: You must purchase new CALs for the newer version.
• With SA: You automatically get rights to the latest version during your SA term.

When is SA essential?

• Cloud or Hybrid Scenarios:
  If you want to use your RDS CALs in Azure or other hosted environments, you need SA because it includes License Mobility rights.
  Without SA, your CALs are tied to on-premises only.

Summary

• On-prem only: SA is optional (for upgrade convenience).
• Hybrid or Azure: SA is mandatory for mobility rights.

4. I want to enable all conditional access what license do I need?

Required License

• Microsoft Entra ID Premium P1 (or higher) is mandatory for any user who is directly or indirectly governed by a Conditional Access policy.
  • Conditional Access is licensed per user, not per tenant.
  • If a user benefits from the policy—even indirectly—they must have the appropriate license.

Licensing Options That Include Conditional Access

• Microsoft Entra ID Premium P1
  • Available standalone or included in:
    • Microsoft 365 E3
    • Microsoft 365 Business Premium
    • Enterprise Mobility + Security (EM+S) E3
• Microsoft Entra ID Premium P2
  • Includes all P1 features plus advanced capabilities like:
    • Risk-based Conditional Access
    • Identity Protection
    • Privileged Identity Management
  • Included in Microsoft 365 E5 or EM+S E5.

Key Compliance Note

• Technically, Conditional Access can be enabled at the tenant level with just one P1 license, but Microsoft licensing compliance requires every user benefiting from the feature to be licensed.

Users not targeted by any policy (and who don’t indirectly benefit) do not need a P1 license.

This first round of testing shows how far AI tools have progressed in understanding Microsoft licensing, and also where they still fall short. Each model delivered useful information, and some provided very strong technical explanations, but the differences in their answers highlight an important truth: AI can support research, but it cannot replace specialist judgement, context, or risk awareness.

Microsoft licensing contains many exceptions, scenario specific rules, version dependencies, and contract based rights that AI cannot interpret in full. Relying solely on an automated answer can still create compliance issues or unnecessary cost. These tools work best when they are used alongside independent licensing expertise that understands environments, contracts, optimisation opportunities, and the commercial impact of every licensing path.

As this series continues, we will compare how each AI tool performs across additional vendors and more complex scenarios, and how organisations can use AI safely and effectively without exposing themselves to licensing or cost risks.