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Help Guide for Patch Management Without Chaos

7 min read

A practical monthly update routine for Windows, macOS, browsers, and key applications. Keep your systems secure without losing productivity to surprise updates.

Written by CTC Editorial Editorial Team

Why Updates Matter

Let's be blunt: unpatched software is one of the easiest ways for attackers to compromise your business.

- **Known vulnerabilities** get published (CVEs)

- **Attackers build exploits** targeting those vulnerabilities

- **Automated tools** scan the internet for vulnerable systems

- **Your unpatched computer** becomes an easy target

The window between vulnerability disclosure and active exploitation is shrinking—sometimes hours, not days. A systematic approach to updates is essential.

The Challenge for Small Businesses

Enterprise IT teams have dedicated patch management systems and staff. Small businesses face different challenges:

- **No dedicated IT person**: Updates fall to whoever's technically inclined

- **Fear of breaking things**: "The last update broke my accounting software"

- **Time pressure**: Staff postpone updates to finish urgent work

- **Varied devices**: Mix of Windows, Mac, phones, each with different update mechanisms

- **Critical applications**: Some software needs testing before updates

This guide provides a practical routine that balances security with business continuity.

What Needs Updating

Critical (Update Immediately)

| Component | Why Critical | Update Frequency |

|-----------|--------------|------------------|

| Operating system | Most exploited | Monthly minimum |

| Browsers (Chrome, Firefox, Edge) | Constant target | Auto-update, check weekly |

| Email client | Phishing vector | Monthly |

| Microsoft Office / Google Docs | Malware delivery | Monthly |

| Security software (antivirus) | Definition updates | Daily (automatic) |

Important (Update Monthly)

| Component | Why Important | Notes |

|-----------|--------------|-------|

| PDF readers (Adobe, Foxit) | Malware delivery vector | Adobe has security updates monthly |

| Java (if still needed) | Frequently exploited | Remove if not needed |

| Flash (remove entirely) | End of life, dangerous | Should not be installed |

| Video conferencing apps | Growing attack surface | Zoom, Teams update frequently |

| Password manager | Protects all passwords | Usually auto-updates |

Business Applications (Test Then Update)

| Component | Approach |

|-----------|----------|

| Accounting software | Test update on one machine first |

| CRM | Check vendor release notes |

| Industry-specific software | Verify compatibility |

| Custom/legacy applications | May need delayed updates |

A Simple Monthly Routine

The Second Wednesday Approach

Microsoft releases patches on the second Tuesday of each month ("Patch Tuesday"). A sensible schedule:

**Second Tuesday**: Microsoft releases patches

**Wednesday-Thursday**: Early adopters report issues

**Friday/Weekend**: Apply updates (if no major issues reported)

Monthly Checklist

**Week 1 (Post-Patch Tuesday)**

- [ ] Review Microsoft patch announcements

- [ ] Check for critical vulnerabilities (Zero-days being exploited)

- [ ] Apply critical/zero-day patches immediately if needed

- [ ] For normal patches, schedule for weekend

**Week 2**

- [ ] Apply OS updates to test machines first

- [ ] Apply OS updates to all machines

- [ ] Update browsers (verify auto-update working)

- [ ] Update Adobe products

**Week 3**

- [ ] Update business applications

- [ ] Test critical workflows after updates

- [ ] Document any issues and resolutions

**Week 4**

- [ ] Review update status across all devices

- [ ] Follow up on any machines that didn't update

- [ ] Plan for any delayed updates

Windows Update Management

For Individual Computers

**Settings** → **Windows Update** → **Check for updates**

Configure active hours to prevent restart during work:

**Advanced options** → **Active hours** → Set your work hours

Using Group Policy (Small Networks)

If you have Windows Pro and a simple network:

1. **gpedit.msc** → Computer Configuration → Administrative Templates → Windows Components → Windows Update

2. Configure:

- "Configure Automatic Updates" = 4 (Auto download, schedule install)

- "Scheduled install day" = 0 (Every day) or specific day

- "Scheduled install time" = After hours (e.g., 03:00)

Using Intune (Recommended)

If you have Microsoft 365 Business Premium:

1. **Intune admin centre** → **Devices** → **Windows** → **Update rings**

2. Create update policy:

- Quality update deferral: 3-7 days (time for early issues to surface)

- Feature update deferral: 30-60 days (major updates need more testing)

- Maintenance window: Set to after hours

- Deadline for updates: 7 days (forces install)

Windows Server Updates

Servers need more careful handling:

- **Never auto-update production servers**

- Schedule maintenance windows

- Update test/dev servers first

- Have rollback plan ready

- Consider Windows Server Update Services (WSUS) for control

macOS Update Management

For Individual Macs

**System Settings** → **General** → **Software Update**

Configure automatic updates:

- Check for updates: On

- Download new updates when available: On

- Install macOS updates: On (or off for more control)

- Install Security Responses: On (small, critical patches)

Managed Macs (MDM)

Use Jamf, Kandji, or similar:

- Defer major OS updates (30-60 days)

- Allow security updates promptly

- Schedule installations after hours

- Notify users before forced updates

Browser Updates

Browsers update frequently and should auto-update. Verify it's working:

Chrome

**Settings** → **About Chrome**

Should show "Chrome is up to date" or update automatically when you visit.

Firefox

**Settings** → **General** → **Firefox Updates**

Set to "Automatically install updates"

Edge

**Settings** → **About Microsoft Edge**

Follows similar pattern to Chrome.

Safari

Updates with macOS system updates.

**Weekly check**: Visit the "About" page in each browser to verify current version.

Application Updates

Microsoft Office

**File** → **Account** → **Update Options**

- Enable automatic updates

- Or manually check: "Update Now"

Microsoft 365 apps auto-update by default. If using volume license, you may need to configure updates.

Adobe Creative Cloud

Creative Cloud app manages updates:

- Set automatic updates on

- Or check weekly

- Major version upgrades may need testing

Other Applications

Many apps now auto-update. For those that don't:

1. **Check on first launch** each month

2. **Enable notifications** for updates

3. **Add to monthly checklist**

Tools like **Ninite** (free for personal, paid for business) can update common applications automatically.

Handling Problem Updates

Before Updating

- **Know your rollback options** (Windows has "Go back to previous version")

- **For critical systems**, test on one machine first

- **Check online** for reports of problems with the update

If an Update Causes Problems

**Windows**:

1. **Settings** → **Windows Update** → **Update history** → **Uninstall updates**

2. Find problematic update, uninstall

3. Pause updates temporarily

4. Report issue and monitor for fix

**macOS**:

1. Boot to Recovery (Command-R at startup)

2. Restore from Time Machine backup

3. Or reinstall macOS (preserves files)

Documenting Issues

Keep simple records:

- Date of update

- What broke

- How you fixed it

- How long to resolve

This helps identify patterns and prepares you for future updates.

Urgent/Zero-Day Updates

Sometimes updates can't wait. Signs you need to act immediately:

- Microsoft releases "out of band" update (not on Patch Tuesday)

- NCSC issues alert about active exploitation

- Security news reports attacks in the wild

- Vulnerability has CVSS score of 9.0+ and is being exploited

**Action**: Apply these updates within 24-48 hours, even if it disrupts normal schedule.

Tools to Help

Free Options

**Windows Update (built-in)**: Handles OS and Microsoft products

**Microsoft Update Catalog**: Manual download of specific patches

**Ninite**: Updates common applications (free for basic use)

**Patch My PC** (home version): Free for personal use

Business Tools

**Microsoft Intune**: Included with M365 Business Premium, manages Windows/Mac/mobile

**Patch My PC** (business): From £2/device/year, automates third-party updates

**PDQ Deploy**: From £500/year, powerful Windows patching

**ManageEngine Patch Manager Plus**: From £200/year, cross-platform

**NinjaOne**: MSP-focused, includes patching

For Macs

**Jamf Pro**: Enterprise Mac management

**Kandji**: Modern Mac MDM with auto-patching

**Mosyle**: Good for smaller Mac fleets

Building a Patch Policy

Document your approach:

> **[Company Name] Patch Management Policy**

>

> **Scope**: All company computers, servers, and managed devices

>

> **Routine Updates**:

> - Operating systems: Within 7 days of release, tested first where practical

> - Browsers: Automatic updates enabled, verified weekly

> - Business applications: Monthly, after vendor testing

>

> **Emergency Updates**:

> - Critical/exploited vulnerabilities: Within 48 hours

> - Authorised disruption to apply if necessary

>

> **Exceptions**:

> - [Legacy system X] updates require [manager] approval and testing

> - Production servers: Weekend maintenance window only

>

> **Responsibility**: [Name/Role] monitors patches and coordinates updates

>

> **Review**: This policy reviewed annually

Authority Resources

- **NCSC Patching Guidance**: [ncsc.gov.uk/guidance/vulnerability-management](https://www.ncsc.gov.uk/guidance/vulnerability-management) - UK government patching recommendations

- **NCSC Early Warning Service**: [ncsc.gov.uk/information/early-warning-service](https://www.ncsc.gov.uk/section/services/early-warning-service) - Free alerts for UK organisations

- **Microsoft Security Update Guide**: [msrc.microsoft.com/update-guide](https://msrc.microsoft.com/update-guide) - Official patch information

- **CISA Known Exploited Vulnerabilities**: [cisa.gov/known-exploited-vulnerabilities-catalog](https://www.cisa.gov/known-exploited-vulnerabilities-catalog) - Vulnerabilities being actively exploited

Monthly Patch Calendar

| Week | Focus | Tasks |

|------|-------|-------|

| **Week 1** (After Patch Tuesday) | Planning | Review patches, prioritise, schedule |

| **Week 2** | Windows/macOS | Apply OS updates, test |

| **Week 3** | Applications | Update business apps, Office, Adobe |

| **Week 4** | Review | Verify all updated, catch stragglers |

| **Ongoing** | Monitoring | Watch for zero-days, auto-update checks |

Getting Started This Week

**Day 1**: Audit—check update status on all computers (Settings → Windows Update)

**Day 2**: Enable automatic browser updates, verify they're current

**Day 3**: Configure Windows Update active hours on all machines

**Day 4**: Create simple monthly checklist (spreadsheet or document)

**Day 5**: Set calendar reminder for post-Patch Tuesday review

**Ongoing**: Follow the monthly routine

Patching isn't glamorous, but it's one of the most effective security measures you can take. A few hours per month prevents vulnerabilities that attackers actively exploit. The routine becomes easy once established—the hardest part is starting.

Frequently Asked Questions

What if an update breaks something important?

For Windows, you can uninstall recent updates via Settings → Windows Update → Update history → Uninstall updates. For critical systems, always test updates on one machine first. Keep records of problems so you know what to watch for next time.

Can't I just set everything to auto-update and forget about it?

For browsers and security software, yes—auto-update is best. For operating systems and business applications, auto-update can cause problems if an update conflicts with your software. A managed approach gives you the security benefit with fewer surprises.

How do I know which updates are critical?

Microsoft labels patches as Critical, Important, Moderate, or Low. Watch for 'actively exploited' warnings—these need immediate attention. The NCSC Early Warning Service and security news sites flag the most urgent issues.

What about legacy software that doesn't support the latest Windows?

This is a business risk that needs addressing. Options: isolate the machine from the network, virtualise it with limited connectivity, or (best) upgrade or replace the software. Running unpatched systems to support legacy software is increasingly dangerous.

How long should I wait after Patch Tuesday before updating?

For most updates, 2-5 days lets early problems surface without exposing you too long. For critical/exploited vulnerabilities, don't wait—apply immediately. For feature updates (major Windows upgrades), 30-60 days deferral is reasonable.

About the Author

CTC Editorial

Editorial Team

The Compare the Cloud editorial team brings you expert analysis and insights on cloud computing, digital transformation, and emerging technologies.