Microsoft is ending support for Windows 10 on October 14, 2025 and the time to start planning is now. We work with a lot of local businesses in the Boston area, and one of the things we hear a lot is - later! It's always a little stressful to think about making a change, and when your "to do" list is long, this is easy to put on the back burner. Delaying your Windows 11 upgrade will only add risk and stress later, so get started now!
If you have a relatively new system, you probably won't need to purchase a new computer - you'll likely be able to just do a software update, which keeps costs a lot lower. When you're on Windows 11, you won't need another upgrade for many years (but security updates along the way are always important).
🛠 What This Means for Your Business
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Security: Staying on Windows 10 after October means no more patches, leaving your business vulnerable to new cyber threats.
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Compliance: Many industries require supported software for data security standards. Are you regulated by HIPAA, FTC Safeguards, CMMC, SEC, IRS Safeguarding Taxpayer Data?
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Software Compatibility: Future apps and services will be designed with Windows 11 in mind.
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Stress Reduction: Planning your upgrade now means avoiding rushed decisions later.
Upgrading to Windows 11 isn’t like learning a whole new system - but there are some interface changes that can trip people up. I recall the first time I wanted to reboot my system in Windows 11 and I couldn't find the power button! I actually had to look it up!
Here are a few common “where did it go?” moments we’ve helped clients with:
🔵Where's the Power Button?
In Windows 10, the Power button was always visible in the bottom-left Start menu.
➡️ In Windows 11, click the centered Start button, then look to the bottom-right corner of the Start menu - you’ll see a power icon for Shut Down / Restart.
This is probably the biggest hiccup for getting used to Windows 11. The start button is "centered", but not in the center, depending on how many items you have in your task bar. On your laptop screen it may be closer to the left, and on a bigger monitor it may be closer to the middle.
By the way, you can modify the look of your Task Bar by right clicking on a blank spot on the Task Bar and select "Taskbar Settings":
From there, you can select "Taskbar Behaviors" and then change from to "left". This is one of the first things a lot of people do after switching to Windows 11.
Quick tip: You can still right-click the Start button and use Alt+F4 on the desktop to bring up shutdown options.
🗂 How Do I Rename a File?
In File Explorer, the right-click menu is now simplified in Windows 11. The “Rename” option may not appear where users expect.
➡️ To rename:
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Click the file once, then press F2
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Or right-click and choose “Rename” icon (a pencil)
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If you don’t see the option, scroll down and click “Show more options” - this opens the classic right-click menu from Windows 10
This behavior is consistent across most file types - but OneDrive files especially may force users to use the “Show more options” menu depending on sync settings.
📁 The Start Menu Looks… Different
Windows 10 had a live tile layout - Windows 11 replaces it with a simpler, cleaner grid. But:
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Pinned apps are now at the top
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All apps list is now a small button in the top-right
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No more dragging shortcuts to Start from File Explorer - you must right-click → “Pin to Start”
💬 Where Did My Taskbar Shortcuts Go?
Windows 11 centers the taskbar icons by default. You can still move them to the left (like Windows 10):
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Go to Settings → Personalization → Taskbar behaviors
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Change Taskbar alignment to Left
Also, drag-and-drop to the taskbar works differently - it was removed in early versions of Windows 11 but has since returned with updates.
🔍 Search Bar Now a Button
Instead of the persistent text field in Windows 10, Windows 11 uses a magnifying glass icon or a floating search bar.
➡️ You can change this in Settings → Personalization → Taskbar → Search
Choose from: Icon only | Search box | Search bar
🖼️ Snipping Tool Has Changed
The old “Snip & Sketch” tool has been merged into the new Snipping Tool with keyboard shortcut Win + Shift + S (one of my favorite keyboard shortcuts I use every day!) - this still works, but it now saves to Clipboard unless you click Save.
📎 Drag-and-Drop to Taskbar
If you're used to dragging files to open them in pinned apps (like dragging a doc to Word on the taskbar), this was temporarily removed in early Windows 11. Microsoft added it back in later builds - so it depends if you’ve kept Windows 11 updated.
🧘♀️ Bottom Line: Different Doesn’t Mean Difficult
Every version of Windows introduces some UI changes, and Windows 11 leans into a cleaner, modern design - but the core functions are all there. With a few minutes of orientation, most users adapt quickly.
And you're not on your own — we're here to guide you and your team through the change, help with training, or even just answer those "how do I do this now?" questions.
📞 Need help planning your Windows 11 rollout or training your team? Let's talk: Contact Us
We offer free 30-minute consultations with one of our top experts to help you stay ahead of the Windows 11 transition - and anything else on your IT roadmap. No pitches. No pressure. Just practical advice to help you make confident, informed decisions. If it turns out we’re a good fit to work with you, great! If not, you’ll still walk away with valuable insight.
About the author:
Ann Westerheim, PhD is the Founder and President of Ekaru, a Technology Service Provider of cybersecurity and IT services for small and medium businesses in the greater Boston area. Ann is an accomplished technology innovator and leader with three engineering degrees from MIT. She has twenty years of high tech experience in research, advanced development, product development, and as an entrepreneur. Her career has spanned a vast range of technology endeavors including research in thin film semiconductors and superconductors, microprocessor fabrication, development of early Internet medical applications, and now focusing on the application of technology in business. She has an avid focus on the "last mile" of technology and decreasing the digital divide.
https://www.linkedin.com/in/annwesterheim/ Let's connect!