Azure IIS & SQL Server Migration – Windows Server 2016 to 2022
Overview
We are seeking a freelance Azure + Windows Server expert to help us migrate our production IIS-based server from Windows Server 2016 to Windows Server 2022, hosted in a new Azure subscription (funded through Microsoft’s Partner Success program).
The server hosts multiple IIS sites and services backed by SQL Server 2017 Express. This is a mission-critical environment that has evolved since 2008 (initially on-prem, then AWS, and now Azure). SSL is currently handled by Let's Encrypt, using win-acme for automatic renewal.
Project Scope
- Snapshot or backup current Azure VM for rollback safety
- Deploy a new Windows Server 2022 VM in a separate Azure subscription
- Install and configure:
- IIS (matching current site and app pool setup)
- SQL Server 2017 Express (to match existing environment)
- Migrate:
- All IIS sites, bindings, app pools, and related content
- SQL Server databases, users, and roles (Express Edition)
- Reconfigure win-acme for Let's Encrypt SSL renewal on the new server
- Harden network and system security (NSGs, RDP restrictions, Windows Firewall)
- Coordinate DNS TTL lowering and safe A-record cutover
- Provide post-cutover validation and support
Requirements
- Strong experience with Azure virtual machines and networking
- Proficiency with Windows Server (2016/2022), IIS, and SQL Server
- Comfortable with SQL Server Express installation and migration (2017 specifically)
- Familiarity with win-acme and Let's Encrypt certificate automation
- Experience handling DNS cutovers with minimal downtime
- Fluent written English (Spanish-speaking applicants welcome)
Details
- We will provide RDP access
- Sites are public-facing but small in scale (low traffic)
- Let's Encrypt SSL automation has worked reliably for over a year
- No Active Directory, clustering, or containerization involved
To Apply
Please include:
- A short summary of your experience with similar IIS + SQL Server VM migrations
- Your hourly rate or fixed project price
- Estimated total hours for the project
- Your availability in the next 1–2 weeks
We're open to offshore applicants. Strong communication and timely coordination are important.