Fall IT Review Checklist: Windows 10 End of Life, iOS 26, macOS, and Budgeting for 2026

Fall is a season of preparation. Farmers harvest their crops, families get their homes ready for colder weather, and businesses should take the time to review their IT. A yearly review is one of the best ways to avoid costly surprises, protect your data, and make sure your technology supports your goals for the year ahead.

This fall, there is more urgency than usual. Windows 10 will reach End of Life on October 14, 2025, which is less than 60 days away. Apple is preparing to release iOS 26 and a new version of macOS, both of which will leave older devices unsupported. Cloud vendors are requiring stronger internet and security standards as they push applications into the cloud. And AI is becoming a valuable business tool that must be implemented carefully to protect sensitive data.

All of these changes make fall the perfect time to review your IT environment and create a budget that sets your business up for success in 2026.

Why IT Reviews Matter

An IT review is like a health check for your business. It highlights what is working well, what is outdated, and what could be putting your systems at risk. Without regular reviews, businesses often end up reacting to emergencies, which usually costs more and causes unnecessary downtime.

A good review covers:

• Devices and systems nearing the end of their lifecycle

• Software licenses that are no longer needed or about to expire

• Security tools that may be outdated or misconfigured

• Internet and vendor contracts that may be overpriced or lacking in service

• User accounts that are no longer in use but remain active. These old accounts can become hidden entry points for cyberattacks. For example, I once reviewed a system for a small business and found accounts belonging to employees who had left years earlier. Those accounts still had access to email and files. If a hacker had guessed or stolen one of those passwords, they would have had direct access to the company’s data without anyone noticing.

• Future needs that should be included in the next budget

The goal is not to spend more. The goal is to plan ahead so that IT costs are predictable and aligned with your business growth.

Real Client Stories

Construction Company: Preparing for the Cloud

I support a construction company that relies on project management and job costing software. Their software vendor recently announced that by 2026, all on-premises servers must be moved to the cloud. That move will bring flexibility and scalability, but it also requires reliable and high-bandwidth internet service.

Their current fixed wireless provider could not handle the bandwidth requirements. On top of that, the provider wanted them to sign a three-year contract with a new equipment install fee. Even after paying those costs, they would still face outages whenever the weather turned bad. The total would have come to about $8,500 per year for unreliable service.

Instead, we reviewed alternatives and moved them to Starlink Business. Their annual cost is now $3,480, which is less than half of what they would have paid. They own their equipment outright, are not locked into a long-term contract, and can scale their bandwidth as their needs grow. By making the switch now, they will save over $5,000 every year and ensure that their cloud transition happens smoothly and without downtime.

Farm: Eliminating Fees and Adding Security

Another client runs a farm with cow monitoring software. During an on-site review, the owner shared plans to expand the monitoring system and add a new computer in another building. When I looked at their internet contract, I discovered they were paying $300 every month in rental fees for equipment. That added up to $3,600 per year with no long-term value.

We built a plan to eliminate those fees by purchasing their own equipment. We also installed a firewall with VPN access, allowing the owner to securely connect to the monitoring database from anywhere on the farm. This eliminated the need for remote access software, which can cost between $600 and $1,200 per year. The firewall also supports Unified Threat Management, adding another layer of protection for their systems and data.

With these changes, the farm will save thousands of dollars every year, strengthen their security, and build a more flexible IT environment to support their growth plans.

Timely Reminders for Fall

✔️ Windows 10 End of Life is October 14, 2025. After that date, Windows 10 devices will stop receiving security updates. Unsupported systems quickly become targets for hackers and can even cause compliance issues in industries like healthcare, finance, and legal.

✔️ iOS 26 will be released soon. Older iPhones and iPads will no longer receive updates. Outdated mobile devices create the same vulnerabilities as unsupported computers. Businesses should inventory their company-owned phones and plan refresh cycles now.

✔️ New macOS release is also around the corner. Macs that cannot run the update will no longer receive support. Unsupported Macs carry the same risks as outdated Windows PCs and should be included in upgrade planning.

✔️ Vendor contracts should be reviewed. Internet providers, VoIP phone services, and even managed printer contracts often have hidden fees or outdated terms. Reviewing these agreements in the fall can uncover savings and ensure the services you pay for match your future needs.

Incorporating AI Safely and Strategically

AI has become part of everyday business life. Tools can draft emails, summarize meetings, and even help analyze reports. But small businesses must approach AI carefully.

When Google confirmed that anonymized ChatGPT conversations had been used for training data, it raised an important question. Where does your data go once it is entered into an AI platform, and is it secure? For businesses that handle sensitive information, this is not just a technical question but a compliance concern.

Safe adoption of AI should be part of every IT review. Businesses can:

• Use business-grade AI tools like Microsoft 365 Copilot or Google Workspace AI that follow existing compliance standards

• Start with low-risk use cases, such as meeting transcription or scheduling help

• Train employees on what data can and cannot be entered into AI platforms

• Establish policies that prevent staff from pasting client or financial data into consumer AI tools

• Budget for AI training so staff can use it effectively and securely

AI can save time and improve efficiency, but it should never put your data or your clients at risk.

Your Fall IT Review Checklist

1. Audit all computers for operating system support, especially Windows 10 devices.

2. Review company-owned mobile devices for iOS 26 and macOS compatibility.

3. Check the internet and vendor contracts for savings and performance improvements.

4. Evaluate cloud migration requirements and bandwidth capacity.

5. Review backup and disaster recovery solutions to confirm they are current.

6. Confirm firewalls and network security tools are updated and effective.

7. Ensure multifactor authentication and password managers are in use across accounts.

8. Review software licenses, renewals, and eliminate unused subscriptions.

9. Audit user accounts to ensure old or inactive accounts are removed and access is properly managed. Old accounts create unnecessary risks if they are forgotten but still active.

10. Assess remote access setups, including VPNs and secure connections.

11. Plan hardware refresh cycles for laptops, desktops, and servers.

    
    

The Bottom Line

Fall is a season of preparation, and your IT should be part of that. By reviewing your systems now, you can identify potential savings, enhance security, and plan for upgrades before they become urgent issues. Whether it is preparing for a cloud migration, eliminating unnecessary costs, upgrading outdated devices, or adopting AI safely, the businesses that plan will be the ones that thrive in 2026.

If you want help with your fall IT review, I can walk you through the process. Together, we can make sure your technology supports your business goals instead of holding you back.