Sooner or later somebody on the leadership team asks it: should we just move to the cloud version?
If you are on SharePoint Server 2016 or 2019, the deadline for that question has already gone by. Both went out of support on July 14, 2026. Same day, both of them. Microsoft has not announced an ESU program for either one, which it did do for Exchange Server.
For most teams the answer is yes, move. But not for the reasons a vendor will give you. Here is what really changes, and the one thing that decides how hard it will be.
The short version, as a decision
Two questions decide it. A 'no' to both points almost every Ontario small business to SharePoint Online.
What you lose
Vendors skip this part. Here is the real list, worst first.
01 Deep customization
.wsp packages), sandboxed solutions, and farm-level features do not exist in SharePoint Online. The way you extend things now is SPFx (SharePoint Framework) and the Power Platform. Some custom code rewrites cleanly. Some has nowhere to go, because the problem is solved a different way now.02 SharePoint Designer workflows
03 InfoPath forms
.xsn templates and the .xml submissions, then rebuild in Power Apps or Microsoft Forms. Allow 4 to 8 hours per form for anything that is not simple.04 Direct SQL and server access
The InfoPath date has already passed. Forms Services shut off in SharePoint Online on July 14, 2026, and that date matters even if you stay on your own servers. More on that below.
What you get
No more server
People underrate this one. You stop patching Windows Server, SQL, the SharePoint binaries, and everything holding them up. In a shop of 10 to 50 people that is 2 to 4 hours a month of admin time that simply goes away.
Collaboration that works the way people expect
Two people editing the same Word file at once. Teams built in. Sharing a file with someone outside the company without standing up a whole extranet farm. The gap between on-prem SharePoint and how people expect to work in 2026 is wide, and staff feel it every day.
Copilot with nothing to install
SharePoint Server has no Copilot built in. Your on-prem content can reach Microsoft 365 Copilot, but only through the SharePoint Server Microsoft 365 Copilot connector. That is a Graph connector, still in preview as of mid 2026, and it needs its own connector agent plus Active Directory sync.
In SharePoint Online, Copilot reads your content natively and there is nothing to set up. If AI is on the leadership wish list, the cloud is the short road. Staying put means building and looking after extra kit to get to the same place.
Compliance gets easier
Microsoft Purview, retention policies, sensitivity labels, DLP. All built in, and far less work to run than the on-prem versions. If anyone is talking about ISO 27001 or SOC 2, that takes a lot of manual effort off the table.
A bill you can predict
One price per user per month. Compare that with Software Assurance plus CALs plus server licences plus SQL plus Windows Server plus hardware plus the hours spent patching it. Under 200 users, the SharePoint Online number is almost always the smaller one.
The file move is the easy part. The real cost is the custom work, and you cannot price what you have not counted.
The thing that decides how big the job is
Two companies the same size can have very different migrations.
A 60-person firm with plain team sites and document libraries is a clean three to six week job. A 60-person firm with a publishing portal, twenty SharePoint Designer workflows and a pile of InfoPath forms is a job measured in months. Same headcount. Completely different project.
This table is the one to bookmark. It is the difference between a guess and an estimate.
| Asset type | Moves cleanly? | Notes |
|---|---|---|
| Document libraries | Yes | SPMT or Migration Manager (both free); ShareGate for large or complex libraries |
| Lists (no custom forms) | Yes | Metadata and views transfer |
| Team sites (no customization) | Yes | Permissions need a review |
| Publishing sites | Partial | No direct modern equivalent, usually a rebuild |
| SharePoint Designer 2013 workflows | No | Rebuild in Power Automate |
| InfoPath forms | No | Rebuild in Power Apps or Microsoft Forms |
| Full-trust solutions | No | Rewrite as SPFx or retire |
| Sandboxed solutions | No | Deprecated in SharePoint Online, remove |
| Custom master pages | No | Modern sites don’t use master pages |
Mostly top rows? The move is quick. Heavy on the bottom rows? Budget for the rebuild. That is where the time and the money go.
The tools, and what they cost
Robocopy will not do it. SharePoint Online throttles you if you push files too hard, so you need a real migration tool. Three are worth knowing in 2026.
- SharePoint Migration Tool (SPMT). Free. You download it and run it. Fine for most volumes.
- Migration Manager. Also free, and already sitting in the SharePoint admin center. It covers file shares, Box, Dropbox, Google Workspace and Egnyte, and you scale it by installing agents on more machines. It does not take SharePoint Server as a source, which Microsoft’s own routing table sends to SPMT instead.
- ShareGate. The paid third-party one people reach for. Worth it on big or messy migrations that need proper reporting and repeat syncs.
Costs people forget
Staying on your own servers. New hardware every 5 to 7 years. SQL licensing, and plenty of SharePoint 2016 farms are quietly running Enterprise SQL. The hours spent patching. Backup kit. Swapping SSL certificates. Windows Server CALs.
Moving to the cloud. Power Automate premium connectors, if your workflows need them. A paid migration tool for anything that is not simple. Time spent on governance, because SharePoint Online shares more freely by default than most on-prem farms do. And cleaning up external sharing, which everyone puts off and which bites about a year later.
When staying put makes sense
SharePoint Server Subscription Edition is the real “stay on-prem” option. It is on the Modern Lifecycle, fully supported, and no retirement date has been announced. That is not true of 2016 and 2019, which both ran out on July 14, 2026.
Staying makes sense in a short list of cases:
- A rule says the data in question cannot go in the cloud.
- You have a site with bad internet where people still need to work on files locally.
- You have a lot of custom work and the business will not pay to rebuild it yet. Fair enough, but Subscription Edition only buys you time. The work does not go away.
One thing it does not save: InfoPath. Forms Services lost support on July 14, 2026 on Subscription Edition too. Staying on your own servers gets you a supported platform. It does not get you your forms back. They still need rebuilding in Power Apps or Microsoft Forms, and the InfoPath forms decision tree sorts each one into rebuild, replace, or bin it before you start.
What I would tell you
For almost any Ontario small business between 10 and 200 users on SharePoint 2016 or 2019: move to SharePoint Online. The time saved, the easier compliance story and Copilot working out of the box all point the same way.
The pain is all in one place, the custom work. If you do not have much of it, there is barely any pain at all.
Which is exactly why you count it first. Site collections, total storage, customizations, workflows, forms. The estimate has almost nothing to do with how many people you employ and almost everything to do with that list. If you want the Canadian dollar ranges that come out the other side, the migration cost and scoping guide has them, plus a worksheet so you can price your own before you ask anyone for a quote.