Room2.09Floor 2 Servers and cloud
Cloud migration for small and mid-size businesses
We help offices retire the server in the closet, deciding workload by workload what moves to Microsoft 365, what moves to Azure or a cloud application, and what is better left on site.
- Retire the server, not just move it
- Files to SharePoint
- Apps to SaaS or Azure
- A plan for what stays local
The server in the closet is running out of time
Many offices still run on a single Windows server bought around 2016 or 2017. It holds the shared drives, signs everyone in, runs the printers and hosts one important application. It has worked quietly for years, which is exactly why nobody has planned what comes next.
Microsoft has set the date for that conversation. Windows Server 2016 reaches the end of extended support on January 12, 2027. After that it receives no security updates unless you pay for Extended Security Updates. Two other deadlines have already passed: Exchange Server 2016 and 2019 left support in October 2025, and SQL Server 2016 followed on July 14, 2026. A server running all three is now three problems at once.
Cloud migration is how most of our clients answer it. Not by copying the old server into the cloud as it is, but by deciding, one job at a time, where each thing the server does should live now.
Workload by workload: where each piece usually goes
A typical office server does seven or eight different jobs. Each has its own best destination, and its own trap to avoid.
| What the server does today | Where it usually goes | Watch out for |
|---|---|---|
| Shared drives | SharePoint sites and Teams, by department | Permissions rebuilt rather than copied, and paths longer than SharePoint’s 400-character limit |
| Personal home drives | Each person’s OneDrive | Old files nobody owns. Decide what to archive before moving |
| Sign-in and Group Policy | Microsoft Entra ID and Intune | Applications that still need Active Directory to log in |
| Print server | Universal Print | Label printers and specialist devices that need their own drivers |
| Email on Exchange Server | Exchange Online | Scanners and applications sending mail through the old server |
| Accounting software with a shared data file | The vendor’s cloud edition, or a hosted desktop in Azure | Never sync the data file through OneDrive. It corrupts |
| Line-of-business application with a database | The vendor’s SaaS version, an Azure server, or staying on site | Vendor support for the new location, and speed over the internet |
| Remote access VPN | Often no longer needed once files and apps are in the cloud | Anything left on site still needs a secure way in |
| Backups | Cloud backup of Microsoft 365 and any remaining servers | Microsoft 365 is not backed up by default beyond short recycle windows |
Each of these has its own page if you want the detail: SharePoint migration, Active Directory and Entra ID, printing and Universal Print and Azure.
Five possible outcomes for each workload
Consultants describe cloud migration with a list of words beginning with R. In plain terms there are five things that can happen to each job the server does, and a good migration uses all five.
Retire it
Every server holds things nobody uses: a database from software replaced years ago, a share for a project that ended in 2019. Switching them off costs nothing and shrinks everything else.
Replace it with a subscription
Many business applications now have a cloud version run by the vendor. Moving to it removes the server, the updates and the backups from your list entirely.
Move it into Microsoft 365
Files, email, sign-in, device management and printing all have a home in licences most offices already pay for.
Rehost it in Azure
Some applications genuinely need a Windows server. Those can run on a server in Azure, in Toronto, reached by staff over a remote desktop or a secure connection.
Keep it on site
Some things belong in the building, and we say so. Those stay on a smaller, supported server or NAS, properly backed up, rather than being forced into the cloud.
Comparing the costs fairly
Cloud migration is often sold as a saving. Sometimes it is. For many offices under 50 people, the total cost over five years ends up similar either way. What changes is what the money buys.
Staying on a server costs
- New server hardware every five to seven years
- Windows Server licences and client access licences
- Backup software, storage and an off-site copy
- Power, cooling and a UPS that needs new batteries
- Patching, monitoring and the occasional weekend failure
Moving to the cloud costs
- Microsoft 365 licences, which many offices already own
- Azure for any application that still needs a server
- Cloud backup for Microsoft 365
- A better internet connection, plus a second one as backup
- The migration project itself, once
The real gains are rarely on the invoice. Staff can work from anywhere without a VPN. There is no single box whose failure stops the office. And there is no deadline like January 2027 to plan around next time. We set both sides out in writing so you can decide on the full picture.
What to fix before anything moves
A migration exposes every shortcut taken in the old setup. These are the things we sort out first, because doing them afterwards is harder.
- The internet connection. Once files and apps are in the cloud, the internet is the office. A second connection from a different provider, with automatic failover on the firewall, stops a cut cable from becoming a lost day. Our networks and firewalls service covers it.
- Sign-in security. MFA for everyone and old sign-in methods switched off, before company data becomes reachable from any browser in the world.
- Clean-up. Duplicate, obsolete and abandoned files are archived instead of moved. Most shared drives shrink by a third or more when someone actually looks.
- Permissions. Years of one-off folder permissions are replaced with simple groups by department, so access in SharePoint makes sense from the start.
- Vendor confirmation. Every application vendor confirms in writing where and how their software is supported before we move it.
When staying on site is the right answer
Cloud is not right for every office, and a provider who says otherwise is selling something. These are the cases where we often recommend keeping some or all of it on site.
- Large design, CAD, video or imaging files opened all day by people in the same building, where local storage is much faster
- Software that controls machinery, scales or production lines and must keep running if the internet drops
- Applications whose vendors do not support any cloud or remote setup
- Sites where a reliable, fast internet connection is not available
In those cases the answer is usually a smaller, modern server or NAS, supported and backed up properly, with everything else moved to the cloud around it. Our server support and server migration services cover that path.
Cloud migration work we quote
Every migration starts with an inventory of what your server actually does, so the quote covers real work rather than a guess at it.
- Server inventory and cloud migration planFixed quote
- Windows Server 2016 retirement projectFixed quote
- File server moved to SharePoint and OneDriveFixed quote
- Active Directory replaced with Entra ID and IntuneFixed quote
- Line-of-business application moved to AzureFixed quote
- Second internet connection with automatic failoverFixed quote
Questions people ask
What happens to our server after January 12, 2027?
If it runs Windows Server 2016, it keeps working, but Microsoft stops releasing security updates for it unless you buy Extended Security Updates. Any flaw found after that date stays open. Cyber insurers and clients increasingly ask about unsupported systems, so the practical deadline is now.
Is the cloud more secure than our own server?
Microsoft's data centres are far better protected than any office closet, but most breaches happen through stolen passwords, not broken-in buildings. Moved to the cloud without MFA and sensible sign-in rules, data can be less safe than before. Moved properly, it is considerably safer, which is why we fix sign-in security first.
Can QuickBooks Desktop or Sage 50 move to the cloud?
Yes, but not by syncing the company file through OneDrive or SharePoint, which risks corrupting it. The options are the vendor's own cloud edition, or running the desktop software on a hosted desktop in Azure that staff connect to remotely. We check which suits your version and how many people use it.
How long does a cloud migration take?
For an office of 15 to 50 people with one server, usually four to eight weeks from inventory to switching the server off, with most of the visible change happening over one or two weekends. Applications that depend on a vendor's schedule can stretch it.
Will our files be slower in SharePoint than on the server?
For everyday documents, no. Files open from the local OneDrive sync and feel the same. Very large files, such as CAD drawings, video or huge Excel models opened all day by several people, can be slower, and those are the cases where we may recommend keeping some storage on site.
What if the internet goes down?
Synced files remain available on each laptop and changes upload when the connection returns, but email, Teams and cloud applications stop until it does. That is why we recommend a second internet connection from a different provider, with the firewall switching over automatically.
Do we still need Active Directory?
Often not. Many offices can sign in and manage devices entirely through Microsoft Entra ID and Intune. Some applications and devices still need traditional Active Directory, and in those cases we keep a small domain controller or run it in Azure until the dependency is gone.
Will we save money?
Sometimes, but it should not be the only reason. Over five years many small offices spend a similar amount either way. The difference is that cloud spending buys flexibility, remote access and no single point of failure, rather than a box that needs replacing. We show both costs side by side before you commit.
Tell us what’s going on
Pick how urgent it is and leave a way to reach you. The help desk replies by phone or email. If work has stopped, call 647-812-3775 instead.
Something broken, or something to plan?
For anything urgent, call. A technician answers the emergency line 24/7. For everything else, open a ticket and tell us what is going on.