Cloud Migration in Aurora, Planned Around the January 2027 Server Deadline
ACT360 moves Aurora businesses off aging Windows servers and onto Microsoft 365 and Azure in tested stages, so a server that loses Microsoft security updates on January 12, 2027 is retired on your schedule, not in a panic.
If your office still relies on a server bought around 2016 or 2017, there is a good chance it runs Windows Server 2016, and that version gets its last Microsoft security update in January 2027. That turns "we should look at the cloud someday" into a decision with a date on it.
How we stage migrations in general is explained on our cloud migration services page. This page is about making that call in Aurora, working from our office at 24 Maple Ave in Barrie.
FREE · 30 MIN · NO OBLIGATION
What We Check in a Free 30-Minute Server Review
An ACT360 partner goes through what your server does today and what each way off it would involve.
- Which Windows Server and database versions you run, and when each stops getting patches
- What depends on that box: files, sign-in, printing, accounting or industry software
- Whether to retire it, replace it or keep one piece local for now, with the reasoning
Why Does January 12, 2027 Matter to an Aurora Business With a Server?
It is the day Windows Server 2016 stops receiving security updates from Microsoft. The server will keep running, but every flaw discovered after that date stays open, and that becomes your problem the next time an insurer or customer asks how your systems are patched.
The date comes from Microsoft itself. Its Windows Server team confirms that extended support for Windows Server 2016 ends on January 12, 2027. Microsoft’s suggested route is an upgrade to a newer Windows Server release, which for a small office often means new licences and new hardware to run them on. The other route is to stop owning a server and move each job it does into Microsoft 365 or Azure.
Aurora’s connections make that second route easier to weigh than it was a few years ago. Stouffville-based telMax broke ground on its first Aurora fibre installations at Wilson Park in October 2023, extending the network it already runs in Newmarket. YorkNet, the Region’s own fibre company, lists a fibre activation in the Leslie and Westview area of Aurora in its 2025 annual report. More fibre choice means more offices and home workers can get the upload speed that makes cloud files feel local. Coverage still varies by street, so we test your actual line before planning.
The server itself is rarely doing just one thing. In a 20-person office it can be holding the shared drive, signing people in, running print queues, hosting an accounting database and kicking off a backup at 2 a.m. Each of those jobs needs its own destination, and some move more easily than others. One Ontario law firm’s move from a vendor-locked remote desktop setup into Azure is a good picture of a staged move; the Azure case study shows how it was sequenced. To prepare before you call anyone, our cloud migration checklist lists what to gather.
What an ACT360 Server Retirement in Aurora Covers
Server Job Inventory
Every role the server plays gets written down: file shares, sign-in, printing, backups, databases and the scheduled task someone set up years ago.
Version and Deadline Check
We confirm which Windows Server and database editions you run and when each loses support, so the plan is built on dates instead of guesses.
Shared Drives to SharePoint and OneDrive
Folders rebuilt in Microsoft 365 with permissions that match how your departments share work today, not how they did in 2016.
Applications to Azure or the Vendor’s Cloud
Accounting, CRM or industry software moved to the vendor’s hosted edition or an Azure virtual machine, once the vendor confirms which works.
Sign-In That No Longer Needs the Server
User accounts and laptop management moved into Microsoft 365, so staff can log in and get updates without the office box.
Retiring the Old Box
When nothing depends on it, we agree with you how its data is archived and when it is switched off, so it doesn’t hum away in a closet for years.
Three Ways to Handle the Windows Server 2016 Deadline in Aurora
These are the realistic options. None is right for every business, which is why the assessment comes before the recommendation.
Our Approach
A.C.T.I.O.N.
For an Aurora server retirement, ACTION starts with one question: what would stop working if this box were unplugged tomorrow? Everything in the plan comes from the answer.
Assess
We go through the server with you and list each role, share and scheduled job, instead of estimating from a user count.
Comprehend
We ask where the business is going. A firm planning to hire, add a site or sell in a few years needs a different end state.
Tailor
You get a written recommendation for each workload: Microsoft 365, Azure, the vendor’s cloud or stay local for now, with a cost and a reason.
Implement
Workloads move one group at a time outside your busy hours, and the server stays on until the people who use each one confirm it works.
Optimize
After go-live, quarterly reviews look at licence counts, cloud spending and anything that changed in the business since the last meeting.
Nurture
We get to know your office manager and the people who phone with problems, so support after the move starts with context.
How ACT360 Keeps an Aurora Server Migration Low-Risk
Financial
The migration is quoted in writing after the assessment, with monthly Microsoft licensing shown separately. The 90-day exit clause covers Managed IT agreements only, not migration projects.
Switching
The old server keeps running until every workload has been tested in its new home.
Political
The Assess step ends with a plain summary you can take to partners or your controller before anyone signs.
Operational
Adam or Jeffrey Bowles stays your contact from the first inventory to the day the server is switched off.
Ownership
Your Microsoft tenant, subscriptions and admin accounts are registered to your business.
What Aurora Owners Ask Before Retiring a Server
Nothing forces the server to shut down on January 12, 2027, but it stops getting Microsoft security fixes that day. After that, every newly found flaw stays unpatched. The real question is how long you’re comfortable running it that way, and what your insurer or your customers will think when they ask.
Sometimes, for the first year or two. A new server avoids monthly cloud fees, but it brings hardware, licences and another refresh roughly five to seven years later. We price both side by side during the assessment, including what your current server really costs to keep running.
Your connection decides which workloads move comfortably, so we test it before planning anything. telMax and YorkNet have both added fibre in parts of Aurora since 2023, but service still varies street by street. Email works fine on a modest line; big shared drives need more upload speed.
Usually, though the route depends on the vendor. Some offer their own hosted edition, some run well on an Azure virtual machine, and a few are better left on a small local machine for now. We confirm with the vendor before quoting, because that answer drives most of the cost.
ACT360 quotes server migrations in writing after the free assessment, because the price depends on data volume, users and how many applications need special handling. Microsoft licensing is billed separately. If you want the new setup looked after afterwards, Managed IT runs $80 to $150 CAD per user per month, and our Aurora managed IT pricing page breaks that range down.
When hands are needed on hardware, such as unplugging the old server or checking the network closet, we come to you. Most planning, configuration and testing happens remotely, and our office at 24 Maple Ave is about 45 minutes up Highway 400. We’re also members of the Aurora Chamber of Commerce.
That depends on what the server does, so ACT360 gives you a schedule after the assessment instead of a guess. A box holding only files moves faster than one running a database and industry software. If not everything can move before January, the review tells you which jobs to move first. Book the free 30-minute call to get that order of work.
Who Plans Your Aurora Server Migration
Two partners, both reachable directly while the work is underway.
Adam Bowles
Partner & CEO15+ years helping Ontario businesses close the gap between the technology they bought and the technology they actually need. Adam asks what the business needs from its systems before anyone talks about servers or subscriptions.
Jeffrey Bowles
Partner & Director of IT ServicesA founding ACT360 team member who trained in computer science at Georgian College. Jeffrey leads the technical side of migrations, along with ACT360’s vCIO and DEEP MSP programs.
ACT360’s six team values, starting with Be the Client, shape how we work inside somebody else’s business during a migration. You can read them on our About page.
Find out what your Aurora server is really doing before January 2027
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