Greg Broiles may call himself a fuddy-duddy (he’s relucant to upgrade from Windows XP), but he’s got some seriously good advice for anyone looking to upgrade Windows:

Always start with a fresh, complete installation on an empty partition or hard disk.

The easiest way to do this is to just buy a new computer with the new OS already installed; you can use both of them in parallel until you’ve got the new one working correctly …

The second easiest way to do this is to buy a new hard disk; take the old hard disk out of your computer and put it somewhere safe. Install the new hard disk, and then install the new OS on the new hard disk as if you’d just bought a new computer.

The third easiest way to do this is to make a complete image backup of your hard disk(s) using something like Clonezilla or Norton Ghost or Acronis True Image.

Seriously, don’t “upgrade” an existing system – best case, you’ll have a working system that’s got a filesystem full of outdated files that just take up space and confuse you (or the computer). Worst case, you don’t have a working system, and will have to restore from the backup you probably didn’t make because nobody ever told you that upgrading is evil.

Greg is 100% correct. Although I don’t follow his advice. Instead, I make sure I have a current backup (I usually have several) of my files, then plow ahead with the upgrade. If it fails, I’ll be up all night reinstalling the operating system and all my software from scratch, then restoring my files. But at least I know I will have a clean install. And for me, it’s just two computers.


  1. Isaac says:

    Sure thing, sir :) Specially when it comes to mobile devices. Upgrade packages for smartphones, for instance, are never clearly described and you never know exactly what you get and what you lose. Sometimes an alleged upgrade will in fact downgrade your device and take away your chance of regreting and going back to the old version.

  2. Ken Vedaa says:

    This is horrible advice.

    For a professional who is likely in possession of a great deal of sensitive information, much of it belonging to clients whom you have an obligation to protect, it is nothing short of negligence to expose this information to the risk of an unpatched windows machine.

    While patching and upgrading is not trivial, basic precautions can mitigate most of the risk. Even if you do not care about your clients, your chance of maintaining a system in a useable manner will only increase when you regularly perform patches and upgrades.

    • Aaron Street says:


      I think you are conflating the concepts of updating (patching security fixes, etc., which is absolutely necessary) and upgrading (transitioning from Windows 7 to Windows 8, for instance).

      • Ken Vedaa says:


        In reality the difference between updating and upgrading is relatively arbitrary, based on the naming and versioning conventions of a particular vendor. It is rather common for vendors to leave significant known security vulnerabilities unresolved in previous versions of an application and/or OS (even if it is still ‘supported’).

        Holding off on an update for a fairly short period of time can be a reasonably calculated risk/reward calculation. Yet, the realistic limitations of this behavior is far shorter than most people seem to realize. The use of XP (or older) as an OS for a system that has access to sensitive data is poor choice, regardless of what patches/updates have been applied.

        It should be noted that these issues also extend beyond the OS to applications as well. One clear example would be a product such as Adobe Acrobat Reader. The ‘X’ version includes a considerable structural change to how the application handles data (e.g. sandboxing) that was not present in versions 9 and before. While Adobe is continuing to provide updates/patches to version 9, users who stick to this version are facing considerably higher security risk than those that upgrade.

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