Upgrading a Windows Operating System

Upgrading an Operating System seems easy, because the vendor wants you to think it is, but... there is a but, a HUGE but.

But, unless you prepare your PC for upgrade and test the upgrade, you are putting your data and system at risk. It is easy to forget, which is why this page was written.

There are a few steps you can take to make the upgrade process smoother:

Check Compatibility

  1. Open Add/Remove Programs from the Control Panel and make a list of all the applications that appear there.
  2. Open System from the Control Panel, go to the Hardware tab and open Device Manager, then make a list of the components in your PC.
  3. Go to the manufacturer website for either the hardware or software and check whether your version is supported by the new operating system.
  4. Download updates and drives for your new OS from the manufacturer's web site or from the vendor's website.

Back up Data

Back up all your important files before doing anything else. The upgrade process is not always a smooth one and you may lose data, so it is best to have a backup just in case.

User files are typically stored in the following locations:

  1. Windows 95/98/Millennium - Default Settings
    %windir%\application data
    %systemdrive%\my documents
  2. Windows 95/98/98SE/Millennium - Profiles Enabled
    %windir%\profiles\application data
    %windir%\profiles\my documents
  3. Windows NT 4.0 -
    %windir%\profiles\%username%\application data
    %windir%\profiles\%username%local settings\application data
  4. Windows 2000/XP/2003 -
    Documents and Settings\%username%\application data
    Documents and Settings\%username%\cookies
    Documents and Settings\%username%\desktop
    Documents and Settings\%username%\favorites
    Documents and Settings\%username%\local settings\application data
    Documents and Settings\%username%\my documents

Before backing up a profile directory or the entire %username% folder in Documents and Settings, purge Temporary Internet Files and Temp Files because they can take up a lot of room. Getting rid of unnecessary data like that can reduce the profile directory size up to 90%.

Some application installations save data and files elsewhere, so it is always a good idea to double check where things are stored and make another backup just to be sure. Investigate any folder in the root of the drive that is not a default folder because you may have inadvertently saved something there.

    Default Folders:
  1. %systemdrive%\common
  2. %systemdrive%\documents and settings
  3. %systemdrive%\program files
  4. %systemdrive%\recycler
  5. %systemdrive%\windows
  6. %systemdrive%\winnt
  7. %systemdrive%\windows update setup

Restoring from backup is always easier than recreating lost data, and having a backup is just a generally good idea so you can store it offsite. Having your backup sitting next to your PC is useless if they both catch fire.

Verify the backup(s) by restoring one or more files to the system. It never hurts to check.


At this point, make sure you have the media for the upgrade, the license key(s) handy, all the drivers on floppy or CD-ROM, and a few hours to kill. You are ready to begin, drop the upgrade media in and start the upgrade process.

NOTE: Windows XP is equipped with an automated compatibility check function before running an upgrade. Anyone thinking about upgrading is encouraged to use that tool before starting an upgrade. It can save a lot of time and effort by identifying applications or hardware that would otherwise be problematic. Insert the Windows XP CD-ROM, then click on Start, select Run, and type [CD drive letter]:\i386\winnt32 /checkupgradeonly or download the Upgrade Advisor from Microsoft. Investigate and troubleshoot any issues reported by the upgrade check before proceeding.

If something should go wrong, check the vendor online help or call someone more knowledgeable before making significant configuration changes.

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