Almost 25 years ago, I wrote a blog post with the title ‘jumping ship slowly’ about leaving Windows (XP was awful, it was mind boggling to me that Vista managed to make people nostalgic for XP). My advice remains the same:

Don’t try switching OS first. The OS is the most easily replaceable bit in the stack. Switch applications first. Most ‘Linux’ apps are cross platform. They’ll run on Windows, and the few that don’t will run in WSL2. You can switch out apps one at a time, and take the time to get comfortable with the alternatives.

Once you’re comfortable not using any Windows-only apps, changing the OS but using all of the same applications is very easy to do. Changing OS and application stack at the same time is an enormous obstacle.

I believe this is also why a lot of corporate and government Linux migrations fail: they try to change everything at the same time and that’s too steep a learning curve.

@david_chisnall
After 2k Pro, XP was not a fond experience for me.

I multibooted OS/2 and Linux until I got early access to test Vista, and it was a revelation (once NVIDIA straightened up their drivers for the new WDDM).

I slowly adopted open data formats, then programs, then finally switched to Alpine Linux for myself and my family.

A long road, but as you noted, it need not be terribly difficult (in many cases).

@Brett_E_Carlock Got any advice or resources you particularly like for Alpine? I'm starting to play with it to replace several things, and I feel like I'm having to relearn a lot of fundamental stuff.

@noodle
I am always availble to help as I can.

I would say the Gentoo and Arch wikis are great, as Alpine tends to do things mostly like Gentoo, and Arch wiki usually always has gotchas documented.

Alpine Wiki is great, but can be outdated.

Main advice: backup /etc/apk/world to versioned backups. I do post-install, post-setup-desktop, post-personal packages, and post-work packages.

Move or copy the backup over world, doas apk fix, software state restored.

Try the default/alpinic way first

@Brett_E_Carlock Do you use autoconfig scripts or similar? For my purposes I'd prefer to rebuild rather than restore when things break. I keep very little data in the first systems I'm replacing.
@noodle this machine has been alpine for 7 years and it's still going. if you're using it as a desktop, i don't think you need to rebuild when something goes wrong, because the sorts of things that go wrong should be easy to repair.
@dysfun
@noodle
Yeah, alpine is pretty bullet-proof, especially when tracking latest-stable.

@noodle
No, I run it for family personal computing, not infra.

The Alpine cloud-init script might be a good base to poke at, as well as the setup-alpine answerfile.

What do you mainly want to use it for?

@Brett_E_Carlock @noodle I've been moving to Alpine from Debian, and the documentation could definitely use improvement. For example, the documentation for apk gives some example commands and says that tags are explained further below, but then tags aren't mentioned at all.

I'm thinking of trying to write a more definitive packaging guide, it's a bit fragmented at the moment.

@mathew
@noodle
Yeah, like almost any volunteer-driven OSS project, docs can fall behind.

I keep telling myself I will step up soon, but time has not been kind.

I am certain they would appreciate any new or fixed up docs/wiki entries.