The week between Christmas and New Year’s is quiet in most offices. It is also the one week many owners have to look at the parts of the business that run in the background, and the first workday of January is when you find out whether they kept running.
A laptop that has been slow for a while won’t start. A software subscription isn’t renewed because the card on file expired. A former employee still has an email account, and no one knows who set the Wi-Fi password, or what it is.
None of this is new. It was there in December, and a short list can help you find these problems. Here is the one we use.
Things that have an end date in 2027
Windows 10 stopped getting regular security updates in October 2025. Microsoft sells a paid program, Extended Security Updates, that keeps Windows 10 computers getting the important fixes for a while longer. For businesses, the first year ended on October 13, 2026, and the second runs to October 12, 2027. Microsoft also says its home version of the program isn’t for business use.
The first year (to October 2026) cost $61 US (about $87 CAD) per computer, and the price doubles each year. A business that signs up for the second year (to October 2027) pays for the first as well. If you have Windows 10 computers you were going to replace anyway, December is a good time to decide whether a year of updates is worth paying for.
Two other dates to know about:
- Windows 11 version 24H2 stopped getting security updates for Home and Pro editions in October 2026. Most computers update to a newer version on their own, but one with updates paused or held back won’t. You can find the version on each computer under Settings, System, About.
- Windows Server 2016 reaches the end of its security updates on January 12, 2027. Most of the businesses we work with have no server, so this applies to few offices, but if you have one, it needs a plan before that date.
Which computers will you replace next year?
Make a list of every computer: who uses it, how old it is, and whether it has been slow, crashing or noisy this year. The oldest ones are added to a replacement list with a rough cost, and that list goes into next year’s budget instead of arriving as a surprise one morning. We wrote about how to tell when a computer is due and about what a small business can expect to spend on IT.
If a replacement is coming anyway, ask your accountant whether buying before December 31 or after makes a difference for your taxes.
Who can still sign in who shouldn’t?
Go down the list of everyone with a login: email, Microsoft 365, accounting software, the shared drive, the phone system, the alarm. Anyone who has left needs to be taken off. So does a contractor from a project that finished in the spring. Each unused Microsoft 365 licence also costs money every month, and we wrote about how to find them.
Shared passwords are the other half of this. If one is on a sticky note or in a spreadsheet, a password manager means it only has to be changed once when someone leaves.
Could you get recently deleted files back by lunchtime?
Most offices have a backup. Few have ever tested restoring from it. Pick one file or one email from a few weeks ago and have it restored, not copied from the folder where it still sits. If it takes more than a few minutes, or no one knows who is able to do it, that is what you need to find out.
Microsoft 365 keeps your files available, but that isn’t the same as a backup.
What renews in January?
Write down every subscription and service that needs to be renewed: your domain name, website hosting, antivirus, Microsoft 365, accounting software, the software your industry depends on. For each one, note the renewal date, the cost, who pays and which email address the notice goes to. That address is often one that belongs to someone who has left.
Losing your domain name takes every service tied to it down with it, including your website and your email, so check that one first. Cancel anything no one uses before it is renewed automatically.
Will last year’s insurance answers still be true?
If you carry cyber insurance, find the application you filled in. Insurers ask about multi-factor authentication, backups, employee training and a plan for an incident, and the answers you gave have to still be true at renewal. If a new employee has no sign-in code, or a backup stopped running in the summer, some of the answers on the form are no longer correct. Those need to be addressed and the form corrected before you renew.
A few hours is usually enough to go through the list and mark which items are fine and which need attention. If you would like our team to go through it with you, book a free 15-minute discovery call and we’ll set up a time.
