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UPGRADING WINDOWS

By Susan Bradley

Windows 20H2 is in the pipeline — so it’s about time to install … its predecessor, Win10 2004.

On October 20, Microsoft tweeted that the October 2020 Update (aka 20H2) has been officially released and will show up over time via a “throttled” rollout. But a few of the tweet’s replies quickly noted that some Win10 users are still waiting for Version 2004 — or had to manually install it. (Microsoft states that the upgrade from Win10 2004 to 20H2 should go faster because it’s more like a monthly update.)

The key to a stable Win10 system is to upgrade when you feel you’re ready. And I’ve finally reached that point for Version 2004. The “spring” release has been out for nearly five months now, giving Microsoft time to fix the more egregious bugs. And early adopters have gotten a good look at the OS.

By now I’ve installed Version 2004 on several test machines at both home and office — and I’ve not run into any major hiccups. (That said, when I upgrade my production systems, I will doubtlessly hit some post-installation snags.)

Before installing 2004 on production business systems, I’ll review installed software and confirm that any specialized apps are ready for Win10 2004. I’ll upgrade my personal systems soon, too, but you can do so when you’re ready … and you have time for it.

A fix for what ails Windows Update: Are you having problems with installing patches via Windows Update? A feature upgrade can be a good way to make WU whole again, as a recent BleepingComputer article showcased.

So here’s my checklist for making sure my key machines are ready for Version 2004.

It should go without saying — but I will anyway — that the first step in any upgrade process is to ensure you have full, recent, and working backups. Only when that’s done should you proceed to the next steps.

Storage space: During the installation process, you’ll effectively have two versions of Windows 10 on your system at the same time. So you need plenty of free hard-drive space. These days, that’s most likely a problem on systems with smaller solid-state drives. (Note that Version 2004 will take up more space than the more incremental 20H2.)

If you’re not sure that you have sufficient disk space, don’t worry; the Win10 installer will check your system at the start of the upgrade process.

On most systems you can typically use the flash drive–based install option. But for really cramped drives, you can download Version 2004’s ISO from the Web and place it on an external hard drive (not a flash drive), then launch the upgrade from that location. I use that technique for my Acer laptop, which has an anemic 35GB drive. (I’m constantly adjusting that device to ensure it has enough space.)

In fact, using an external drive and an ISO is the only way I’ve been able to get a feature release installed on the Acer. My external Western Digital drive automatically reconnects after installation reboots, allowing the upgrade process to continue. So when in doubt, have an external hard drive handy.

For a typical upgrade, a free-space buffer of at least 20GB should be more than enough for installing a semi-annual “feature” release. Keep this in mind: If you’re struggling to free up space on a nearly full hard drive, it’s probably time to look for a larger drive before moving to the next version of Win10.

Note: Upgrading the drive on some laptops is nearly impossible. And leaving your machine at a computer-repair store during the pandemic might be equally problematic. So when I purchase a new portable, I usually opt for the largest and fastest drive offered.

If Microsoft deems your machine ready for a new release of Windows 10, you can initiate the upgrade from Windows Update (WU). But on machines that I’ve previously had difficulty upgrading, the process often goes better with a Win10 ISO rather than via WU. Microsoft’s handy Media Creation Tool (download page; click the Download tool now button) lets you build either an ISO file or a flash drive–based installer. The flash drive is easier for a one-time install, but the ISO file is a better option if you want to reinstall Version 2004 (or any other older Windows release) down the road.

Warning: Now that Version 20H2 has been released, the Media Creation Tool will no longer download Win10 2004 — just 20H2. So hopefully you have a Version 2004 ISO stashed away, as we’ve recommended in several articles. If not, you’re probably better off sticking with Win10 1909 for now — or use the Rufus option discussed below.

Assuming you do have a 2004 ISO, simply double-click it; that’ll mount the Windows 10 installer as a new virtual hard drive on your system. Next, click setup.exe, and Version 2004 will install on top of your existing system — without impacting your existing files. It’s essentially the same process as doing an in-place repair/reinstall.

Figure 1. Win10 2004’s installer system opens on a virtual drive. To start the upgrade process, simply double-click setup.exe.

The Rufus option: The drawback of Microsoft’s Media Creation Tool is that it supports only the most recent Win10 release. But the third-party Rufus app lets you download any older version of Win10. (Please note: In order to use the “download” option, you must follow the instructions to update Rufus and then close/relaunch the app.) Rufus can be a bit quirky. For example, on my Lenovo laptop, it did not offer several Win10 versions. But on my HP desktop PC, all older releases were shown. (I suspect the difference was due to the relatively small drive on the Lenovo.)

Figure 2. Use Rufus to download past versions of Windows 10.

Bottom line: I recommend getting comfortable with downloading Windows 10 ISOs — regardless of the source — and with saving them to external storage.

Set aside some time: As a general rule, a feature upgrade should take about 30 minutes, start to finish. If it takes significantly longer, it probably means you have a really slow Internet connection — or an exceptionally slow hard drive or PC. Our redoubtable AskWoody editor has a mere seven-megabits-per-second download speed to his small tree farm — on a good day. Upgrades are measured in hours.

(Microsoft employees have undoubtedly been spoiled with extremely good broadband. But as more of its staff become from-home workers — more or less permanently — it’ll be interesting to see whether they spin out any changes to Win10 that will help those of us with slow Internet speeds.)

If you have robust bandwidth, but your machine still has a traditional spinning-platter drive, you should seriously consider upgrading to a solid-state device. That’ll help future upgrades go more quickly.

With more of us now working from home — or staying at home or having never left home — now might be a good time to assess your technology needs. If you have a slow laptop, keep in mind that you can find relatively inexpensive refurbished computers. They’re an excellent value and often come with a warranty. Also, don’t skimp on the spec: generally, the more powerful the PC, the longer it’ll remain viable.

When I’ve purchased new/used systems equipped with older IDE hard drives, I’ve used upgrade kits to transfer the data from an existing computer to a new hard drive.

After a feature upgrade, check that your key applications still work. For example, I typically have to use Intuit’s “PDF and Component Repair tools … ” (download site) following a major update.

Next, I make sure that all printers are properly set up and operational. Early feature releases often reset these devices to their default drivers, thus wiping out my printing customizations. Fortunately, recent updates have been better behaved. But every new upgrade is a spin of the roulette wheel.

The older the device, the more it might fight the upgrade. For example, Microsoft recently changed its policy on third-party drivers. As Microsoft noted, “Starting with [the October] release, Windows will require the validity of DER-encoded PKCS#7 content in catalog files. Catalog files must be signed per section 11.6 of describing DER-encoding for SET OF members in X.690.” (BleepingComputer has a translation.) In short, Microsoft is ensuring that malware doesn’t ride into your system disguised as a driver.

Consequently, when installing a third-party driver, you might receive the error message “Windows can’t verify the publisher of this driver software.” You might also see “No signature was present in the subject” when attempting to view the driver’s signature using File Explorer.

None of these issues is the direct result of a feature update, but they could crop up after the upgrade is complete. Just be aware that, from now on, Windows will block any OEM or manufacturer driver that it can’t verify. (HP warned about the issue in a recent alert — more info.)

Finally, if you’ve been beating your head against the wall in trying to upgrade an older device, it might be time to find an alternative use for it — or retire it. It all comes down to your perseverance. Personally, as I’ve gotten older, my tolerance for misbehaving technology has decreased significantly. Now, I’ll simply discard/recycle a device that no longer works properly or fits my needs.

Forewarned is forearmed: As with any update, keep an eye on Version 2004’s list of still-outstanding issues. Bookmark its Health Dashboard. And I’ll say this once again: Make sure you have a good backup before you upgrade. With that and an ISO, you can decide when it’s the right time for installing 2004.

Stay safe out there!

In real life, Susan Bradley is a Microsoft Security MVP and IT wrangler at a California accounting firm, where she manages a fleet of servers, virtual machines, workstations, iPhones, and other digital devices. She also does forensic investigations of computer systems for the firm.

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Fellow Loungers suggest various causes for a sudden jump in junk mail — hacked ISP servers, compromised email lists, visiting sketchy sites — the ways are many and the solutions few. Have you been hit by a wave of spam? What was your solution?

If you’re not already a Lounge member, use the quick registration form to sign up for free.

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