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Tales of Windows and woe

· 3 min read

Normally, installing Windows (or Linux for that matter) is nothing to write about.

However, over the past year I've ran into one surprising blocker after another.

To prevent more wasted troubleshooting hours, I've put all of these together.

Getting the image

Microsoft makes Windows client ISO images available to download, and has for years now.

These are forced to be downloaded via the media creation tool if the download site detects your browser platform as Windows.

Otherwise the ISOs are offered for direct download.

However, even the download (direct or otherwise) can be not what it seems.

Verification

Linux pros take it as given that downloads (and media creation) can fail in subtle ways.

Every Linux ISO download I've seen has a corresponding cryptographic hash, allowing verification.

Unfortunately, Microsoft does not provide this.

This can lead to a multitude of interesting outcomes:

  • ISO is downloaded by Media Creator which does know about the expected hash/checksum

    • Media Creator will refuse to create media, but not inform the user as to why

  • ISO is downloaded directly - and cannot be verified. Installation will fail at some illogical point:

    • installation will fail citing bad serial key, but failure happens before serial is asked for
    • installation will proceed and then hang at file copy dialog
    • installation will complete but Windows then will have sporadic instability, e.g. inability to wake from sleep

The last one is notably hard to diagnose as the problem is quite removed from the cause.

Never skip ARM day

Windows on ARM is also offered from the same page.

MS seems to update the actual image less often than x64, yet, the labelling is updated.

This leads to major confusion when installing ARM64 Win11 that was downloaded and named as, say, 25H2, but turns out to be 24H2 - for no apparent reason.

Given that e.g. Intune features require specific release versions, this can make troubleshooting a rather interesting experience.

Installing Windows without Windows

As it is, Windows Media Creator only runs on Windows.

Directly writing the ISO image to removable media isn't designed to work, either.

Usually, this isn't even a problem - if one is installing Windows, chances are, there is access to an existing Windows install, or a virtual machine.

However, it is always nice to have options.

After testing a few USB creators, one that I have been able to observe working consistently is Ventoy.

While typically used to provide the option of booting multiple different Linux environments, it works for Windows as well - only caveat being Secure Boot.

Secure Boot will need to be disabled in order to boot the installer - once Windows itself is the boot target, Secure Boot can be enabled.