Move your Windows estate to Akamai Cloud. Licensed correctly, and run for you.

Akamai Cloud has no marketplace Windows image, and its native backup service does not cover NTFS disks. Maxima migrates Windows Server and SQL Server workloads to Akamai, resolves your licensing position, and takes 24/7 operational ownership after cutover.

Get your Windows estate and licensing assessment

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Why it’s time to move your Windows to Akamai now

The 2016 estate is out of time.

Windows Server 2016 reaches end of extended support on January 12, 2027. SQL Server 2016 left support in July 2026. After those dates you are choosing between Extended Security Updates, an in-place upgrade, or a move. All three mean touching the servers. 

Windows on hyperscalers carries a license premium in every instance-hour.

AWS license-included pricing bakes the Windows Server license into the hourly rate on every instance, every hour, whether the machine is busy or idle. Bringing your own licenses instead means dedicated hosts/instances, which is a different kind of expensive. 

Single-vendor dependency has become a board-level topic.

Leaving the hyperscaler entirely is rarely realistic. Moving the workloads that do not need to be there, and keeping a VPN back to the ones that do, usually is.

What actually goes wrong when you move Windows

There is no Windows image to click.

Akamai's custom image upload accepts gzipped raw images up to 6 GB uncompressed, formatted ext3 or ext4. A Windows Server disk is NTFS and considerably larger than that. The standard image path simply does not open for Windows, and teams usually discover this after the project has been approved.

The machine boots and then cannot see its own disk.

Akamai Cloud runs on KVM. A Windows image built for AWS has no VirtIO storage or network drivers, so it boots to a stop code with no disk and no network. The drivers have to be slipstreamed into the install media before the first boot, not added afterward.

You lose the console at the worst moment.

When Windows fails to boot on a remote hypervisor, RDP is gone and you need out-of-band access. That means Emergency Management Services enabled in the image and console access wired through LISH before you need it. Configured after the fact, it is worthless.

Platform backups quietly do not cover you.

Akamai's native backup service expects ext filesystems. A raw NTFS partition is not covered. Teams migrate, see "backups" in the console, and only find out the Windows machines were never in scope when they try to restore one.

Active Directory decides the sequence, not the project plan.

Domain controllers, DNS, group policy, and domain-joined applications determine what can move and in what order. Move an application server away from its DC without planning the identity path and authentication breaks in ways that look like network faults.

SQL Server is a separate project inside the project.

Edition, version, licensing model, and high-availability design all change the answer. Always On availability groups, failover clustering, and shared-storage assumptions do not survive a naive lift and shift.

How we approach it: Five phases, one accountable team

Phase 0: Estate and licensing assessment.

Inventory every Windows and SQL workload, its version, its dependencies, and its license position. Identify what is domain-joined, what is node-locked, and what has to stay. Output is a move, keep, or modernize call per workload plus a modeled Akamai cost. 

Phase 1: Landing zone.

VPC and VLAN design on Akamai, two-way VPN back to whatever stays as is, identity path for Active Directory, object storage cutover from S3 to Akamai's S3-compatible Object Storage, and a WAF to replace the AWS one. Nothing migrates until the destination is real.

Phase 2: Golden image build.

VirtIO drivers slipstreamed into upstream Microsoft media, Emergency Management Services enabled for console recovery, RDP hardened behind a bastion rather than exposed, static addressing, activation path confirmed, and monitoring and backup agents baked in. One validated image, not five hand-built servers.

Phase 3: Rehearsed cutover.

Test environments move first and stay up as a reference. Production moves per workload, in a maintenance window, with the AWS side left intact and a rollback path until the new environment has proven itself. Automated pipelines and pre-validated templates are what make the window short.

Phase 4: Day-2 operations.

24/7 monitoring and incident response, a backup and disaster recovery design built specifically because the platform's native backups do not cover these disks, Windows Update ring management and patch windows, certificate and secret management, and cost governance so the savings do not erode in month six.

Stop stitching together cloud tools, contractors, and incident response. One managed team to migrate, secure, and run your applications 24/7

Get your Windows estate and licensing assessment

Why your Microsoft licenses behave differently on Akamai

Microsoft splits cloud providers into two groups.

Listed Providers are AWS, Microsoft Azure, Google Cloud, and Alibaba Cloud. Everyone else is an Authorized Outsourcer. Akamai Cloud is in the second group, and that single fact changes what you may do with licenses you already own.

Since October 2022, the Flexible Virtualization Benefit lets customers with active Software Assurance or subscription licenses deploy Microsoft server software on an Authorized Outsourcer's infrastructure, including shared multi-tenant hardware. That benefit does not apply on Listed Providers. On AWS, running Windows Server on licenses you already paid for means dedicated hosts or dedicated instances, and most teams give up and pay the license-included rate instead.

In practice this gives you three paths, and the assessment tells you which one you are on:

Your position

What it means on Akamai Cloud

Active Software Assurance or subscription licenses

Bring them. Flexible Virtualization covers deployment on shared hardware. No new license purchase.

Perpetual licenses without active Software Assurance

Not eligible to bring. New licenses are procured as part of the migration, typically around $1,320 per VM.

Mixed estate

The common case. Some workloads bring licenses, some get new ones, and the assessment prices both.

Two infrastructure consultants talk while looking at a laptop screen

Not everything should move

An assessment that recommends moving everything is a sales document, not an assessment. Workloads we routinely advise leaving alone:

  • Domain controllers where the forest has to stay put for compliance or latency reasons
  • Applications with hardware-locked vendor licenses where the vendor will not reissue
  • Anything depending on nested virtualization, since it is not available
  • SQL Server high-availability designs that assume shared storage, until they are redesigned rather than moved
  • Workloads under a vendor certification that names a specific certified cloud
  • Anything scheduled for decommission inside twelve months, where the migration cost never pays back

Proof: Done in production, not in a lab

A US market-analytics platform, fintech. Running entirely on AWS at roughly $30,000 a month, with no FinOps practice and no SRE layer, and a board-level objective to reduce single-vendor dependency. Five Windows servers had to come along: three production, two test.

What we did:

  • Migrated the estate from AWS to Akamai Cloud over a six-week fixed-price engagement
  • Built and licensed the five Windows servers on Akamai, since no marketplace image exists
  • Moved S3 to Akamai's S3-compatible Object Storage and stood up two-way VPN connectivity between the Kubernetes nodes and the AWS infrastructure that stayed
  • Replatformed Kafka, PostgreSQL, and the chatbot services onto Kubernetes, replacing single-VM databases with self-healing, auto-scaling clusters
  • Replaced the AWS WAF with a Cloudflare WAF at roughly $200 a month
  • Wrapped the result in SRE-as-a-Service: 24/7 incident response, observability, GitOps and CI/CD, DevSecOps, backup and disaster recovery, secret and certificate management

Result: monthly cloud spend fell from about $30,000 to about $18,700, a reduction of roughly 35%. The original proposal modeled 25 to 30%. Execution beat the estimate.

What it costs: Fixed price to move, monthly retainer to run

We publish ranges because the shape of the commercial model matters more than the exact number, and because the number depends on your estate.

Migration: fixed price, from approximately $11,000 for a small estate, typically delivered in six weeks. Scope drives the number: workload count, Windows server count, database complexity, and how much has to stay connected to AWS.

Managed SRE after cutover: from approximately $5,400 a month for 24/7 coverage, incident response, observability, patching, and backup.

Windows licensing: zero additional cost where Flexible Virtualization applies to licenses you already hold. Approximately $1,320 per VM where new licenses are procured.

Check if you should migrate with Maxima Consulting

A fit if:

Not a fit if:

You run Windows Server or SQL Server workloads on hyperscalers and the bill is above roughly $10,000 a month

You want contractors to manage day to day

You have estate facing the upcoming deadline

Your estate is a handful of small VMs where the migration cost will not pay back

Reducing dependency on a single hyperscaler is an actual objective, not a slide

You need someone to sign off on your Microsoft license compliance, which no partner legitimately can

You have no dedicated FinOps or SRE function, and cannot justify hiring one

You want one team accountable for the migration and for what happens afterward

Contact us

Get your Windows estate and licensing assessment

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Frequently Asked Questions

Does Akamai Cloud support Windows Server?
Windows runs on Akamai Cloud, but not through a marketplace image. Akamai's custom image upload accepts gzipped raw images up to 6 GB uncompressed on ext3 or ext4 filesystems, which a Windows disk does not fit. The working method is a custom install with VirtIO drivers slipstreamed into upstream Microsoft media and console access enabled through LISH. Maxima builds and operates these images as a managed service.
Can I bring my existing Windows Server licenses to Akamai Cloud?
If your licenses have active Software Assurance or are subscription licenses, yes. Akamai is not a Microsoft Listed Provider, so the Flexible Virtualization Benefit introduced in October 2022 applies, and it permits deployment on shared multi-tenant hardware. Perpetual licenses without active Software Assurance are not eligible and need to be replaced. The assessment establishes which of these describes your estate.
Why is licensing different on Akamai than on AWS?
Microsoft designates AWS, Azure, Google Cloud, and Alibaba Cloud as Listed Providers, and excludes them from the Flexible Virtualization Benefit. On AWS, using licenses you already own generally requires dedicated hosts or dedicated instances. On an Authorized Outsourcer such as Akamai, licenses with Software Assurance can be deployed on standard shared compute.
What happens to backups? I heard the platform does not cover Windows disks.
That is correct and it is the most common post-migration surprise. Akamai's native backup service expects ext filesystems, so a raw NTFS partition is not covered by it. Backup and disaster recovery for Windows workloads have to be designed separately, and that design is part of the migration scope, not an afterthought.
How long does a Windows migration take?
A small estate, in the range of five to ten Windows servers alongside other workloads, is typically a six-week fixed-price engagement. The variables are Active Directory dependencies, SQL Server high-availability design, and how much has to stay connected to AWS afterward.
What about SQL Server?
SQL Server is scoped separately from Windows Server because edition, version, and high-availability design all change the licensing and the migration approach. Always On availability groups and failover clustering are redesigned rather than lifted. SQL Server 2016 left support in July 2026, so a 2016 estate is a modernization decision, not just a move.
Can you guarantee we are license compliant?
No, and neither can any other partner or cloud provider. License compliance is between you and Microsoft. What we do is document your position, model the options, procure where you need new licenses, and give you the evidence trail. Any vendor telling you they carry that risk for you is selling you something they cannot deliver.
Do you keep running it after the migration?
That is the intent of the model. Managed SRE covers 24/7 incident response, monitoring, patching, backup and disaster recovery, and cost governance. We would rather be accountable for the running system than only for the migration project.