Back then Windows had already blessed Windows Installer packages (.msi), which could be installed unattended from the CLI. But, to be fair, many companies still

Back then Windows had already blessed Windows Installer packages (.msi), which could be installed unattended from the CLI. But, to be fair, many companies still preferred to use other installer tools, including sometimes Microsoft themselves (e.g. ClickOnce). But there's been improvements. The winget CLI can now install and update several well-known applications, and even upgrade them when you first downloaded them any other way. There's also the MSIX package format, which is much closer to distro packages or mobile apps, can auto-update without a central repository and supports sandboxing. Nowadays, even if still a bit hacky, I definitely consider Windows packaging less painful than the mess that is Linux distribution. Packages in distro repositories are regularly outdated, and every other package is installed misconfigured or has been patched in unclear ways by the distro maintainers; then there's Flatpak which make for gigantic installs with clunky sandboxing, or AppImages.