Hands-On Tech 232: Enrolling in Windows 10 Extended Security Updates

Date: September 7, 2025
Host: Micah Sargent
Topic: How to stay secure on Windows 10 after end-of-life by enrolling in Microsoft’s Extended Security Updates (ESU) program for consumers.

Episode Overview

This episode tackles a timely issue: how everyday users can keep their Windows 10 systems secure beyond the official end-of-life date (October 14, 2025) by enrolling in Microsoft’s new Extended Security Updates (ESU) program—something previously available only to business clients. Micah Sargent answers listener Kevin’s question about the available enrollment options, the rollout process, eligibility, and tips for those who don’t yet see the ESU option. The episode also features helpful listener follow-ups on KVM setups and password manager selection.

Key Discussion Points & Insights

1. Listener Question: How to Enroll in Windows 10 ESU (00:00–11:43)

• Listener Kevin’s situation: He’d like to use Microsoft Rewards points to enroll in ESU (as his computer cannot move to Windows 11 due to software compatibility) but isn’t seeing the option in Windows Update.
• Micah's Summary:
  • Microsoft is offering three ways for consumers to enroll in Windows 10 ESU:
    • Paying $30
    • Redeeming 1,000 Microsoft Rewards points
    • Syncing your PC settings and apps to the cloud (via Windows Backup in OneDrive)
  • The ESU program began rolling out in mid-August 2025 through Windows Update.
  • The option to enroll should appear in Windows Update for eligible users running Windows 10 version 22H2 in participating regions (notably, the US).

Notable Quote:

• “At some point, you should be able to hop in there and see that option has appeared for you. My suggestion for you, Kevin, is if you do not see that change by mid September, then it's probably worth at that point reaching out to Microsoft support.” – Micah Sargent [04:45]

What To Do If the Option Doesn't Appear (04:30–07:15)

• Keep checking Windows Update regularly and ensure your system is up to date.
• Avoid unwieldy workarounds (like logging out and back in with your Microsoft Account) as the timing of ESU activation isn’t critical until closer to October 14.
• If not available by mid-September, reach out to Microsoft support.

Enrollment Timing and Coverage (07:16–10:30)

• The ESU program covers you with updates until October 13, 2026.
• The sooner you enroll, the more coverage you get—enrolling after October 14, 2025, shortens your protection period.
• After that cutoff, devices not enrolled or upgraded to Windows 11 lose:
  • Technical support
  • Feature updates
  • Quality/security updates

Notable Quote:

• “You really want to make this happen … before October 14th. Because at that point, you’re not getting any more than what you have now. It's on October 14th that that stops.” – Micah Sargent [06:08]

Eligible Devices & Regions (10:31–11:43)

• Only certain Windows 10 devices (running version 22H2) and regions (including US) are eligible.
• Enrollment is handled via Windows Update, followed by a transaction through Microsoft Store.

2. Follow-up: KVM Switch Experiences & Tips (11:44–15:40)

Listener Heath builds on Micah’s previous advice around using keyboard-video-mouse (KVM) switches for handling multiple computers with multiple monitors.

Main Takeaways:

• KVMs often present problems like windows “jumping around” between monitors—especially without EDID (extended display identification data) emulation.
  • “Look for [EDID emulation] as an option if you’re worried about that being an issue for you.” – Micah Sargent [13:45]
• Switching between different operating systems (ex: macOS and Windows 11), three monitors, and using DisplayMaid (macOS) can help manage window positions.
• If using a USB hub, make sure it’s powered (not just bus-powered)—important for devices like webcams.

Pro tip:

• If you’re a Windows user and do not have 4K displays, less expensive KVMs may suffice, but always check for EDID emulation if multi-monitor accuracy matters.
• For macOS users, window management tools like DisplayMaid are very helpful.

3. Follow-up: Finding the Right Password Manager (15:41–18:56)

Listener Jim follows up on password manager recommendations, seeking a solution for shared use with his technophobic wife.

Micah’s Recommendations:

• Micah uses and endorses 1Password, especially the family plan ($4.99/month, $60/year).
• Suggests that the more tech-comfortable partner should test solutions alone first before introducing them to less enthusiastic partners.

Notable Quote:

• “You don’t want to involve your SO in doing the experimenting with tech if they are not techie people themselves; it’s only going to result in them not wanting to use whatever solution you’ve come up with.” – Micah Sargent [17:35]

Memorable Moments & Notable Quotes

• On the ESU Transition:
  • “If you enroll after October 14th, when they’re done with Windows 10, you’re getting a shorter period of time, so you’re not getting as much for your money… So you really want to make this happen… before October 14th.” – Micah Sargent [06:08]
• On KVM Switches:
  • “Windows tend to jump around when switching from one computer to another. If the switch doesn’t have what’s called EDID emulation… more expensive switches are more likely to have [it].” – Heath, as read by Micah Sargent [13:45]
• On Family Password Sharing:
  • “You and Leo have filled in some of the gap for my missing help desk.” – Jim [18:20]
• On Listener Involvement:
  • “Love to hear from you if you followed through with one of the fixes I've suggested, or if you are able to answer a question that comes up on the show in a new or novel way…” – Micah Sargent [11:43]

Timestamps for Important Segments

| Time | Segment | |-----------|----------------------------------------------------| | 00:00 | Introduction / Listener Kevin’s ESU question | | 02:01 | ESU Program Overview and Enrollment Options | | 04:30 | Troubleshooting the Missing ESU Option | | 07:16 | Enrollment Timing, Coverage, and Urgency | | 10:30 | Eligible Devices & Regions Explained | | 11:44 | Listener Heath’s KVM Follow-up & Practical Tips | | 15:41 | Listener Jim’s Password Manager Feedback |

Listener Community Engagement

• Micah encourages ongoing feedback and new questions:
  • “If you have questions that you would like answered, hotwit TV is how you get in touch with me. We love to hear from you, love to answer your questions…” [18:56]

Summary

This episode is a practical toolkit for all Windows 10 users facing end-of-support, with a clear roadmap for joining Microsoft’s ESU program and tips to ensure you maximize your protection window. The listener-driven format highlights real-world concerns and provides detailed technical guidance—not just on ESU but also on advanced home setups and family tech management.

Perfect for:
Anyone seeking to keep their tech secure—and functional—without making a hasty upgrade, and anyone who appreciates crowd-sourced tips for optimizing complex setups.