How to Keep Your Business Software Up to Date Without Breaking Anything

What you will need: about 30 minutes to set up, one computer you can use as a "test machine," and a recent backup of your important files.

Software updates fix security holes and bugs, but now and then one causes a new problem, like a printer that stops working or a program that won't open. You don't have to choose between updating and staying safe. A simple test-first habit gets you both.

Quick definitions

• Update (or patch): a new version of a program that fixes problems or adds features. "Patch" usually means a small fix.
• Security update: an update that closes a weak spot attackers could use to get into your computer.
• Line-of-business app: the specialized software your company runs on, such as accounting, scheduling, point-of-sale, or industry-specific programs.
• Release notes: the software maker's short summary of what changed in an update.
• Backup: a separate copy of your files, kept somewhere other than the computer itself.

Step 1: Make a list of what you use

You can't keep track of software you've forgotten about.

1. Write down the main programs each computer uses: Windows or Mac apps, web browsers, and any line-of-business apps.
2. Next to each one, note who handles its updates: automatic, you, or the software vendor.
3. Mark the critical ones, the programs that would stop work for the day if they broke.

A simple spreadsheet or a page in a notebook is enough.

While you're at it, check your Windows version. Microsoft stopped free security updates for Windows 10 on October 14, 2025. A Windows 10 computer that isn't enrolled in Microsoft's paid Extended Security Updates program no longer gets security fixes, and no update routine can change that. Plan to upgrade or replace it.

Step 2: Confirm your backup works

Before any update, make sure you could undo a bad one.

1. Check that your most recent backup finished successfully.
2. Confirm you can open at least one file from it.
3. For line-of-business apps, find out where their data lives: a folder on your computer, a database on a server in your office, or the vendor's cloud. If it's on your own equipment, make sure your backup includes it. If it's in the vendor's cloud, the vendor runs the servers, but ask how you can export your own copy of your data if you ever need it.

New to backups? Our guide to the 3-2-1 backup rule covers the basics.

Step 3: Pick a test machine

1. Choose one computer to get updates first. Ideally it's one that is used regularly but isn't mission-critical.
2. If you're a one-person office, your test machine is your only computer. In that case, update at the start of a quiet day, not before a deadline.
3. Always update the test machine first, then the others.

Step 4: Update on the test machine

Windows

1. Open Settings, then Windows Update.
2. Select Check for updates.
3. Install what's offered and restart when prompted.
4. For apps from the Microsoft Store, open the Microsoft Store, go to Library, and select Get updates (or Update all, depending on your version).

Our guide on how to check for Windows updates has more detail.

Mac

1. On macOS Ventura or later, open the Apple menu, then System Settings, then General, then Software Update. On older versions, it's Apple menu, then System Preferences, then Software Update.
2. Install what's offered.
3. For apps from the App Store, open the App Store and select Updates.

Safari, Apple's browser, is updated through Software Update along with macOS.

Web browsers

Browsers are a favorite target for attackers, so keep them current.

• Chrome: menu (three dots), then Help, then About Google Chrome. It checks for updates and may ask you to relaunch.
• Edge: menu (three dots), then Help and feedback, then About Microsoft Edge.
• Firefox: menu (three lines), then Help, then About Firefox.

Most browsers download updates on their own but only finish installing them when you restart the browser. If you leave yours open for weeks, close and reopen it.

Menu names change from time to time. If yours looks different, search the browser's help page for "update."

Line-of-business apps

These need extra care, so slow down.

1. Read the release notes before installing.
2. Check that the new version works with your version of Windows or macOS. Vendors usually list this on their website or support page.
3. If the update changes how the program stores data, make a fresh backup first.
4. If you're unsure, contact the vendor's support and ask, "Is this update safe to install now?"

Step 5: Run a quick test

After updating, spend five to ten minutes checking the things your business can't do without.

1. Open your critical programs and make sure they start.
2. Try your everyday tasks: open a file, send an email, print a page, run a report, or process a sample sale.
3. Check that your internet, printer, scanner, and card reader still work.
4. Write down anything odd, even if it seems small.

If everything works, use the computer normally for a day, then update the other machines. If something breaks, stop and see "If something goes wrong" below.

Step 6: Know when to wait a few days

Waiting is fine for some updates, but not for others.

Install promptly (within a day or two):

• Security updates, especially ones the vendor describes as fixing a problem attackers are already using.
• Browser updates.

Wait a few days, and let the test machine go first:

• Major version upgrades, such as a new version of Windows or macOS.
• Updates to line-of-business apps, especially ones that change how the program looks or stores data.
• Updates that arrive right before a busy period such as month-end, payroll, or a big sale.

Wait for the vendor's go-ahead:

• Large operating system upgrades when a critical app hasn't been confirmed as compatible yet.

Waiting a few days gives the software maker time to fix any early problems, and gives other users time to report them. The wait shouldn't turn into weeks or months, though, because older software keeps its security holes.

Step 7: Set up a routine

1. Pick a regular time, such as the first quiet morning of each week, to check for updates.
2. Turn on automatic updates for browsers and low-risk apps.
3. For critical line-of-business apps, keep updates manual so you control the timing.
4. On Windows, you can pause updates for a short time if the timing is bad. Look for the Pause updates option in Windows Update. How long you can pause depends on your version, so treat it as a short delay, not a way to skip updates.
5. Keep a simple log of the date, what you updated, and whether anything went wrong.

If something goes wrong

1. Restart the computer. This fixes more problems than you'd expect.
2. Check the software maker's support page for known issues with that update.
3. Don't update the other computers until you know what happened.
4. Contact the vendor's support for line-of-business apps.
5. Consider rolling back, which means returning to the previous version:
   • Windows: in Windows Update, open Update history, then Uninstall updates to remove a recent one. After a major Windows upgrade, you can usually go back to the previous version for about 10 days, under System, then Recovery.
   • Mac: there's no simple undo button for macOS updates. This is what your backup is for.
6. Restore from your backup if files or data are affected.

Quick checklist

• List of programs and who updates each
• Windows 10 computers identified and planned for
• Recent backup confirmed
• Test machine chosen
• Release notes read for critical apps
• Quick test completed after updating
• Security and browser updates not delayed
• Weekly update time on the calendar

If you're in Southeast Michigan and would like help setting up an update routine for your office, get in touch with us.