What are the cheapest and easiest upgrade paths to Windows 8?

Updated November 2, 2012

With Windows 8, Microsoft has reduced the number of editions it's selling. In theory, that makes the buying and upgrading process easier than it was before. But easier is not the same as easy. There are still plenty of gotchas in the process.

If you're planning to upgrade to Windows 8, these are the current answers to the questions you're most likely to have. I plan to update this post several times as more details emerge and some of these products move from "pre-order" to "ship."

You should read this article even if you plan to skip Windows 8 and stick with Windows 7. If your new PC comes with Windows 8, you can spend a relatively small amount to secure downgrade rights that could save you a very large amount later.

See also:

• Prices and packaging for Windows 8 go public
• How the new Windows 8 license terms affect you
• How to skip Windows 8 and continue using Windows 7

I've broken this post into upgrade scenarios. If you've got a scenario you don't see covered here, use the Feedback form at the bottom of this post to send me a note.

You’re planning to buy a new Windows 8 PC.

Choose your OS version carefully. Most consumer PCs are sold with the base Windows 8 edition. This is the most economical time to purchase an upgrade to Windows 8 Pro. If you want to use downgrade rights to replace Windows 8 with Windows 7, you need Windows 8 Pro; you also need the Pro version to add Media Center capabilities and to join a Windows domain.

Be careful: Not all PCs include the option to upgrade to Windows 8 Pro. For example, the 5 PCs included on the Windows 8 pre-order page at Dell’s Consumer site come with Windows 8 only. No option is available. You have to go to the Business site to get that option, which currently costs $70.

You've purchased a new Windows 8 PC and want to upgrade to Windows 8 Pro.

If you've purchased a new PC with Windows 8, you can go to Microsoft's Add Features page and order the Pro Pack.

Currently, this option costs more than a Windows 8 Pro upgrade from Windows 7, Vista, or XP. More details here. 

You have an existing desktop PC or notebook that came with Windows XP, Vista, or Windows 7 and was purchased before June 2, 2012.

You have two options:

• You can order the Windows 8 Pro online upgrade from Microsoft for $40. Note that you can order the upgrade on a different PC than the one where you plan to install it. (You’ll need to use the option to create bootable installation media on a DVD or USB flash drive.) You can order a backup DVD for another $15. You'll find more details about the ordering process here. If you have questions about prices and upgrade paths, see this FAQ.
• Purchase a boxed upgrade to Windows 8 Pro from a reseller like Newegg, Amazon, or Staples. The current discounted price in the U.S. is $70, with some resellers offering slight discounts, free shipping, and so on. (I imagine big-box discounters like Walmart and Costco will have this product eventually.)

You have an existing desktop PC or notebook that came with Windows 7 and was purchased between June 2, 2012, and January 31, 2013.

Lucky you. You qualify for an upgrade to Windows 8 Pro for $14.99. Go to the Windows Upgrade Offer site to register. First. write down your Windows 7 product key (the one from the side of the PC (or for some laptops, in the battery compartment or on the power adapter). You'll need it to verify your eligibility for the discounted upgrade.

You want to install Windows 8 in a virtual machine on a Mac or PC.

A virtual machine is treated as if it were a new PC. See the next question.

You want to install Windows 8 on a new PC that you built or bought that did not include a Windows license.

You can preorder an OEM copy of Windows 8 that includes Personal Use Rights. Two weeks before the Windows 8 launch, those prices are around $100 for Windows 8 and $140 for Windows 8 Pro.

However, I recommend waiting until October 26 to see what price Microsoft offers on downloadable full licenses. I suspect that during the promotional period the discount will be significant.

You have a new Windows 8 PC and you want to add DVD playback capabilities and Media Center software.

If it’s a new PC that came with the base edition of Windows 8, you need the Windows 8 Pro Pack (currently $70 or less from online retailers). This product uses the same technique as Windows 7 Anytime Upgrade to unlock the Pro features on your installed copy. You use the Add Features option to enter a new product key, which you can buy online or as a key card in retail packaging.

If you upgraded Windows 7 or Vista or XP to Windows 8 Pro, regardless of which method you used (online or boxed software), you qualify to add the Windows 8 Media Center Pack for free.

Currently, Microsoft is offering the Pro pack for $70. The Media Center Pack is free for a limited time from the Add Features page. When the promotion ends, the Media Center Pack will be $10.

You want to downgrade to Windows 7.

If you purchased a new PC with Windows 8 Pro installed by the OEM, you can use your own Windows 7 media to install Windows 7 Professional. You’ll need to activate your copy over the phone using the product key from the sticker on the PC.

If you bought a new PC that included the base edition of Windows 8, your only official downgrade path is to buy a retail copy of Windows 7 and install that.

Upgrade copies of Windows 8 Pro do not include downgrade rights.

For more on downgrade rights, see “How the new Windows 8 license terms affect you”  and "How to skip Windows 8 and continue using Windows 7."