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Automating Windows Setup via Chocolatey

Vinay Hegde on July 25, 2021

When you're a software professional, 1 thing you must've dreaded is setting up a new Windows machine (as in a development environment). This might ...
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jonrandy profile image
Jon Randy πŸŽ–οΈ β€’

The steps I usually use are:

1) Download the iso image for Ubuntu
2) Make a bootable USB drive
3) Wipe Windows with Ubuntu
4) Proceed from there

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vinayhegde1990 profile image
Vinay Hegde β€’ β€’ Edited

@jonrandy +1 if that's sarcasm but you could lessen effort even further by not installing Windows at all

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jonrandy profile image
Jon Randy πŸŽ–οΈ β€’

I didn't. Damn near impossible to get a machine with Ubuntu pre-installed here in Thailand

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vinayhegde1990 profile image
Vinay Hegde β€’

Hard luck there! It can be skipped if an assembled PC is available but a laptop will surely come with Windows pre-installed so now I know why step 3 is needed.

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djibe profile image
djibe β€’

Hi,
I did the same performance with Winget recently.
And Winstall (winstall.app/) is awesome for this.

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jonjpbm profile image
jonjpbm β€’

"The winget tool is currently a preview, so not all planned functionality is available at this time."

docs.microsoft.com/en-us/windows/p...

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vinayhegde1990 profile image
Vinay Hegde β€’

Yes I remember winget isn't live yet so it won't be usable for all. Also chocolatey is relatively evolved and supports more functions along with a super helpful community.

Thanks for the ideas @jonjpbm and @djibe

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jonjpbm profile image
jonjpbm β€’

Also

"The winget tool requires Windows 10, version 1809 (10.0.17763), or a later version of Windows 10."

Which might be limiting.

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vinayhegde1990 profile image
Vinay Hegde β€’ β€’ Edited

Unsure how you interpeted circular logic out of those 2 comments, let me make it easier

Tweaking Windows to one's preferences is difficult as Microsoft doesn't permit changes to the OS or any components in it. They also have a history of botched OTA updates.

This then leads people to stay away from customisations & ignore future updates willfully as they don't want to tamper a working environment & impact their daily work.

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vinayhegde1990 profile image
Vinay Hegde β€’ β€’ Edited

That's because of a handshake between Microsoft's arcane documentation and burnt child dreads the fire experiences people have had when tinkering with Windows until now. But it does seem Windows 11 will change that perception for the better.

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vinayhegde1990 profile image
Vinay Hegde β€’

Looks interesting but any specific reason one should prefer Freshbuild over any of the above installers?

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vinayhegde1990 profile image
Vinay Hegde β€’

Please re-read my previous comments, I already have.

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vinayhegde1990 profile image
Vinay Hegde β€’ β€’ Edited

Scoop has more dev tools + an extras bucket for non-dev stuff (Skype, Slack etc..) but some apps are either missing or a bit dated.

Overall very promising, thanks for the info

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vinayhegde1990 profile image
Vinay Hegde β€’

When it's Windows, people aren't intentionally uninformed but rather due to unawareness or little/no choice/lack of alternatives.

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vinayhegde1990 profile image
Vinay Hegde β€’

Useful feature but multiple managers could mess up app installs or cause interference with one another.

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vinayhegde1990 profile image
Vinay Hegde β€’

@sharpninja what exactly do you mean by this?

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vinayhegde1990 profile image
Vinay Hegde β€’

I agree, but from observation people don't do it proactively for Windows