Guides on how to switch operating systems

MacBook, coffee mug, and cactus

Updated on May 14, 2023

New computers often beg the question “how do I move my files/settings/apps to my new machine?” It’s especially so if one’s switching operating systems, or needs to move between OSes easily.

I thought I’d round up in one post some online resources explaining how to move to various operating systems.


While Windows is the dominant computer operating system, Microsoft is still concerned about losing market share. On the high end, there’s MacBooks, while on the low end, there’s Chromebooks and tablets (including the iPad). As such, Microsoft’s been trying to lure users at both ends back to Windows. Their TV ads leave much to be desired in this regard, however, whether the “Scroogled” anti-Chromebook ads from last year or the forced-rhyme-using Surface Pro 3 vs. MacBooks ads from this year (“it’s got a USB,” indeed).

On the better side, Microsoft’s recruited HP to produce the Stream laptop to try to fight Chromebooks at the low end, along with the Surface for the high end against MacBooks/iPads. They’ve also produced an online guide on how to switch from OS X to the Surface. However, I’d say it applies to anyone moving their files, music, etc. from OS X to Windows.


Apple’s been trying to lure people to OS X, of course, especially with the rise of MacBook sales. Similar to Microsoft, Apple also has a guide explaining some OS X/Mac basics to those that’ve switched from Windows.

Elsewhere online, Macworld has an extensive guide explaining how to buy a Mac, transferring files from a Windows PC, and OS X software/operating system equivalents to those in Windows.

Finally, I’ve written about my move a few years ago from Linux back to the Mac.

Chrome OS

Google’s written a basic guide for new Chromebook users, including how to set up a Chromebook, a tour of Chrome OS, and a list of Google/Chrome equivalents to common Windows/OS X desktop software.

Intel’s also taken a shine to Chrome OS lately, to the point they’ve written a program, Intel Easy Migration, designed to transfer files from various OSes to Chrome OS.

Of course, I’ve written a few posts on Chromebooks/Chrome OS, including about what apps I’ve found useful.


There’s a variety of Linux user guides online. Ubuntu has one for those moving from OS X, Windows, or another Linux distribution.

For Linux Mint, I’ve written my own post-installation guide.

(Updated 10/22/15)


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Anthony Dean

Anthony Dean is the owner of Diverse Tech Geek and Diverse Media Notes.

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