How to Make a DOS Bootable USB Key, The Easy Way

This article provides simple instructions for creating a DOS bootable USB key from within Microsoft Windows. This is one of those operations that in theory should be extremely simple to perform, but there appears to be a lot of incomplete and even incorrect information online. So here we are. First, the tools and files that you will need:

  1. Download a boot disk from bootdisk.com. In this example, I will use the Windows 98 SE image, called boot98se.exe. Annoyingly, these files were created using an ancient version of WinImage’s Self-Extracting utility.
  2. Consequently, you will need to download WinImage by Gilles Vollant. The utility is shareware, but will run as a 30 day trial without registration. Alternatively, you can use the free utility Virtual Floppy Drive 2.1 to accomplish the same effect, but that approach won’t be covered here.
  3. Download the HP USB Disk Storage Format, V2.1.8. This is the official version directly from Hewlett-Packard’s site; avoid downloading this tool from third-party sources as many of those sites appear to be questionable.

That’s it for the needed files. Now to create the actual USB bootable USB key:

  1. Install WinImage as well as the HP USB Disk Storage Format Tool.
  2. Open boot622.exe from within WinImage. Under the Image menu, select Extract, and find a convenient location for extraction.
  3. Open the HP USB Storage Format Tool, select your USB device, and select Create a DOS startup disk. Browse for the DOS system files located at the directory from the previous step.
  4. Copy all of the files, such as command.com on to the USB key.

If you’re not sure that your system is capable of booting from USB in the first place, try the pre-built USB Boot Test to determine your motherboard USB compatibility.

Windows Server 2008 Password Complexity Requirements

When trying to change the Windows 2008 Administrator password, I immediately received the following error message:

Unable to update the password. The value provided for the new password does not meet the length, complexity, or history requirements of the domain

But what exactly are the default password requirements? This is described in the Windows Server 2008 Security Guide, under Domain Policy Settings:

  • Passwords cannot contain the user’s account name or parts of the user’s full name that exceed two consecutive characters.
  • Passwords must be at least six characters in length.
  • Passwords must contain characters from three of the following four categories:
    • English uppercase characters (A through Z).
    • English lowercase characters (a through z).
    • Base 10 digits (0 through 9).
    • Non-alphabetic characters (for example, !, $, #, %).