Windows 10 Retirement FAQs For Business Owners.
- Oakland Solutions
- Aug 16
- 2 min read
Photo courtesy of Adem Erkoc
Answers to the most common questions Oakland Solutions gets from business owners like you.
Can’t we just keep using Windows 10 after October?
Technically, yes, but we strongly advise against it. After October 14, 2025, Microsoft will stop releasing security updates. That means your systems won’t be protected against new threats, and cybercriminals will be actively targeting known vulnerabilities.
What’s the actual risk of doing nothing?
The main risks are:
Increased chance of phishing, ransomware, and malware attacks
Software compatibility issues as new apps stop supporting Windows 10
Compliance problems (especially in healthcare, finance, law, etc.)
Insurance claims being rejected due to unsupported systems
Will we lose any data during the upgrade?
No. We’ll back everything up before we touch a single thing. Documents, emails, bookmarks, printer settings, it all comes across with you.
What if some of our apps don’t work on Windows 11?
We’ll check compatibility with your key tools before upgrading. If anything needs adjusting or swapping, we’ll talk it through with you first.
How much downtime should we expect?
Most upgrades take 1–2 hours per device. Replacements take 3-4 hours per device. We’ll schedule everything to fit around your team’s workday so there’s no disruption to your operations.
What happens if we wait until September or October?
We expect a serious rush industry-wide as the deadline approaches. By planning now, you avoid scheduling bottlenecks, higher costs, and last-minute scrambling.
Can we just do this ourselves internally?
In theory, yes, but it’s rarely smooth.
Upgrading a business computer isn’t just about clicking “update.” It involves backing up critical data, checking software compatibility, reconfiguring printers, accounts, shared drives, and more. We’ll handle all of that for you (plus the post-upgrade support), so you avoid mistakes, downtime, or grumpy staff 🙂
Have more questions?
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