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I have a Windows laptop(old) and a Mac laptop(new) and have lots of pictures, music, and documents on Windows laptop. Also I'm aware of the fact that the programs I have installed won't carry over to Mac, but that's fine. I already have an external hard drive where I can backup my Windows laptop data to.

What would be the best strategy to backup everything from Windows laptop and then restore it all on Mac laptop as painless as possible?

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I'm assuming this is a one-time file transfer.

Honestly, just copy and paste your files using Windows Explorer and Finder.

It'll take you longer to set up an application or script to do it. Unless you have 10+ distinct unnested directories, it'll be faster to copy everything manually through your external drive.

On the Windows side, you'll probably want to grab these folders:

  • Documents
  • Pictures
  • Videos
  • Music

On the Mac side, copy those complete folders to their matching folders in your home directory.

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