Microsoft On-Premise to Cloud Migration Cost Estimator
Answer 8 questions to estimate the licensing, infrastructure, and migration costs of moving from on-premises Microsoft to Azure and M365.
3-5 Yr
TCO Horizon
8
Questions
3 min
To Complete
Question 1 of 8Microsoft Cloud Advisory
Question 1 of 8
🏢
How large is your on-premises Microsoft estate?
Estate size drives migration complexity, timeline, and cost.
Small — under 50 servers, under 500 users
Medium — 50-200 servers, 500-2,000 users
Large — 200-1,000 servers, 2,000-10,000 users
Enterprise — 1,000+ servers, 10,000+ users
Question 2 of 8
💻
Which on-premises Microsoft products are in scope for migration?
Each product has different migration paths and licensing implications.
Primarily Exchange/Office — moving to M365
Exchange, SharePoint, and Windows Server
Full stack — Windows Server, SQL, Exchange, SharePoint, AD
Full stack plus legacy apps dependent on Windows Server
Question 3 of 8
💰
What is your current annual Microsoft on-premises licensing cost (including SA)?
Your current spend is the baseline for cloud cost comparison. Cloud should deliver equal or better value.
Under $500K/year
$500K-$2M/year
$2M-$10M/year
$10M+/year
Question 4 of 8
☁️
What is your target cloud architecture?
Lift-and-shift (IaaS) vs re-platform (PaaS) vs replace (SaaS) dramatically affects costs.
SaaS-first — M365, Azure AD, minimal IaaS
Mix — SaaS for productivity, IaaS for servers
Lift-and-shift — IaaS-dominant migration
Undefined — no clear architecture decided
Question 5 of 8
🔐
Do you have regulatory or compliance requirements affecting cloud migration?
Data residency, industry regulations, and security requirements can limit cloud options and increase costs.
Minimal — standard enterprise requirements
Moderate — data residency requirements manageable
Significant — regulated industry (financial, healthcare)
Extensive — government, defence, or highly regulated
Question 6 of 8
📅
What is your migration timeline?
Migration timeline affects parallel running costs, staffing, and transition licensing.
24+ months — phased approach
12-24 months — structured migration
6-12 months — aggressive
Under 6 months — very aggressive
DC exit pressure often drives poor decisions
Question 7 of 8
👥
Does your team have Azure migration experience?
Lack of internal expertise increases dependency on external consultants and migration risk.
Yes — experienced Azure team
Some — team has basic Azure skills
Limited — primarily on-premises skills
None — will need significant external support
Question 8 of 8
📜
Have you assessed the licensing implications of migration?
Transitioning from on-premises to cloud changes your licensing model (perpetual to subscription). Costs may increase or decrease depending on approach.
Yes — full licensing cost model built
Partially — high-level cost estimate
No — infrastructure costs estimated but licensing unclear
No cost assessment done
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