Windows Server and Exchange
Support for the Windows servers GTA offices still rely on, and a plan for what replaces them at end of support. Exchange 2016 and 2019 are already past it, and Windows Server 2016 follows on January 12, 2027.
The server in the back room still matters
Plenty of GTA offices still run a Windows server on site. It handles staff logins, shared drives, printers, an accounting or line-of-business database, and sometimes an Exchange email server. We support these servers day to day and plan what replaces them when Microsoft stops releasing security updates. Some of those deadlines have already passed.
The calls we get are familiar. Nobody can log in on Monday morning. The S: drive is full. A server warranty ran out three years ago. The person who set up Exchange left long ago and took the admin password with them. Each one has a fix, and the fix is easier when someone has written down how the server is set up.
| Server and Exchange work | Managed plan |
|---|---|
| Help desk and on-site calls when a login, shared drive or printer fails | Included |
| Adding staff, changing folder permissions, resetting passwords | Included |
| Server hardware, Windows Server and Exchange licences | Billed separately |
| Windows 10 Extended Security Updates | Billed separately |
| Azure usage after a move to the cloud | Billed separately |
| Server replacement, Exchange migration, Windows 11 upgrades | Fixed quote |
How many servers you run is one of the things that sets where your office lands in the managed plan’s per-user range. The pricing page explains the rest.
End-of-support dates to check now
When Microsoft ends support for a product, it stops releasing public security fixes. The software keeps running, but later flaws stay open unless you pay for extended updates.
Three products common in GTA offices are at or near that point: Exchange Server 2016 and 2019, Windows Server 2016 and Windows 10. Here is where each stands as of October 2026.
- Exchange Server 2016 and 2019: end of support was October 14, 2025. No more public security updates.
- Windows 10: end of support was October 14, 2025. Businesses can buy Extended Security Updates for a limited time.
- Windows Server 2016: extended support ends on January 12, 2027.
An Exchange server is the most urgent of the three. It faces the internet by design, because it receives your email, and Exchange servers have been a favourite target for attackers for years. Running one without security updates puts your mailboxes, and often the rest of the network, at risk.
Not sure what you are running? Open a ticket with your server names, or call, and a technician will check the versions with you.
Windows 10 PCs after end of support
Windows 10 stopped getting free security updates on October 14, 2025. Businesses can pay Microsoft for Extended Security Updates, priced per device, but it is a stopgap. The price doubles each year, joining late means paying for the years you missed, and the updates cover security fixes only. The lasting answer is Windows 11 or a replacement PC.
Windows 11 needs TPM 2.0 and a supported processor, and many older PCs do not meet those requirements. We check each machine and sort them into three groups: upgrade in place, replace, or cover with Extended Security Updates for a short while because it runs equipment or software that cannot move yet.
Upgrades are booked in batches so a whole department is never offline at once, and each user’s files, printers and email are checked before the job is signed off. Replacement PCs are quoted with the hardware listed separately. If budget means spreading this over a year, our IT planning service can set the order.
Replace the server, or move to Microsoft 365 or Azure
When a server reaches end of support, each job it does can go one of three ways: a new server running a current version of Windows Server, Microsoft 365, or Azure. Most offices end up with a mix. We look at each job separately and recommend what will cost least over the next several years.
Email on Exchange Server
For most small and mid-size offices, the answer is Exchange Online in Microsoft 365. Microsoft runs the server, applies the security updates and keeps it available. If you must keep email on site, Exchange Server Subscription Edition is Microsoft’s current on-premises version, and its licences need an active subscription or Software Assurance. We migrate mailboxes, shared mailboxes, room calendars and public folders either way. The Microsoft 365 page walks through a typical move.
Shared drives
Files on a server share can move to SharePoint and OneDrive, which removes the need for a VPN to reach them from home. Large files, such as engineering drawings, video or scanned archives, sometimes work better on a new on-site server or storage device. We look at how your staff use the files before choosing.
Logins and line-of-business software
Staff logins and device policies can move to Microsoft Entra ID in the cloud. An accounting or industry application usually decides the rest: some vendors support Azure, some need a server on site, some have moved to their own cloud. We ask your vendor before we quote, so the plan fits the software you actually use.
Server projects quoted as fixed prices
Server replacements, migrations and Windows upgrades are planned as fixed-price projects, agreed before any work starts. The quote names each server, what happens to every job it does, the hardware and licences needed, and when staff will notice the change. Day-to-day help with the servers you keep is part of ordinary support.
- Exchange 2016 or 2019 mailboxes moved to Exchange OnlineFixed quote
- Exchange 2019 upgrade to Subscription EditionFixed quote
- Windows Server 2016 replacementFixed quote
- Shared drives moved off an end-of-support serverFixed quote
- Windows 10 to Windows 11 upgrades by batchFixed quote
- Windows 10 PC inventory and replacement planFixed quote
Questions people ask
What do Ontario small businesses need to know about Windows 10 end of life?
Windows 10 stopped getting free security updates on October 14, 2025. PCs still work, but new flaws stay unpatched. Businesses can buy Extended Security Updates per device as a short-term bridge, with the price doubling each year. The lasting fix is upgrading eligible PCs to Windows 11 and replacing the rest.
When does Windows Server 2016 support end?
Extended support for Windows Server 2016 ends on January 12, 2027. After that date, security updates come only through Microsoft's Extended Security Updates program. Plan the replacement or migration now, because ordering hardware, moving data and testing line-of-business software can take several weeks once the work is approved.
Can we keep using Exchange Server 2016 or 2019?
It will keep running, but both versions reached end of support on October 14, 2025 and no longer get public security updates. Because an Exchange server receives email from the internet, it is exposed by design. Most offices should move to Exchange Online in Microsoft 365; the alternative is Exchange Server Subscription Edition.
Should we replace our server or move to the cloud?
Decide job by job. Email almost always belongs in Microsoft 365. Shared files often move to SharePoint, but very large files may suit a new on-site server. Line-of-business software depends on what its vendor supports. We look at each job the server does and recommend the cheapest option that will last.
Are Windows 10 Extended Security Updates worth buying?
They are worth it for machines that cannot be replaced yet, such as a PC running equipment or software that will not work on Windows 11. They cover security fixes only and cost more each year, so use the time they buy to finish your upgrade plan.
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.