A smooth, slightly dangerous upgrade

ITworld.com –

Four of my last five articles have been more or less tutorial in nature, so I thought it was time for a slight change of pace. If you missed my previous column, you can read it here.

This week, I'm going to discuss the process of upgrading from Windows 95 to Windows 2000 Professional. I'm not going to give a lot of technical detail, just some insights about how well I think Microsoft has designed the process for performing the upgrade in a managed, corporate environment.

For the most part, I have to say that the upgrade was seamless and thorough when I tried it. During the initial few steps, the setup program ran a utility to check if currently installed applications were compatible with Windows 2000. For example, it identified WinPopup.exe, installed in the Startup Program Group, as an incompatible program, because Windows 2000 -- like Windows NT -- installs the Messenger Service, which basically takes over the same functionality.

On a scale from 1 to 10, I'd give this particular feature a 7 -- well above average. It queries all programs installed on a system and verifies them against a list of those it actually knows to have problems, or that have upgrades available. It even gives links to additional information.

After the compatibility check, the installation routine asked a few preliminary questions and then told me it would reboot three times during the upgrade -- a lot, but at least you're warned in advance. It then proceeded with the upgrade, and I went to lunch.

When I got back, the system was completely installed; all I had to do was set some passwords for accounts it had created for me. Basically, it looked through the existing profiles, created an account to match each profile, and asked me to create a password for each account.

This is a potential problem. Even though this makes upgrading easier for the everyday home user, for corporate use it isn't very secure to have the Administrator password be just anything the user wants. Even a blank password worked in this case. The system should instead recommend a strong password -- a combination of alphanumeric characters of different cases and in a random order, such as "R8nLF44vM" -- for the Administrator account, and then allow you to set passwords separately for each of the accounts it creates for you.

If you were upgrading a large number of desktops in a managed corporate environment, you would probably automate this, setting it up to create a strong password and adding the Domain Administrators group to the local Administrators group. This last step lets administrators control the machine without having to know the Administrator password. If the desktops in a managed environment have all the user accounts stored on a domain controller, the issue of passwords can be ignored.

After I set the passwords, the installation routine started Windows 2000 and I saw a desktop that almost mirrored my previous Windows 95 desktop. I was amazed -- it actually worked. I would not have thought you could upgrade a personal operating system such as Windows 95 to a professional business operating system such as Windows 2000 so easily and with so few problems.

It's possible that I just got lucky, of course. For one guy I talked to, the system hung in the middle of the upgrade when the program was detecting hardware. He had to restart the system, which left the system in an inconsistent state and unable to be successfully booted. He thinks the problem was due to a graphics card, but -- the question of blame aside -- nothing was logged and he wasn't given any warning. Luckily, he was experienced enough just to format and do a fresh install. More importantly, he had a backup of his data.

I would recommend that Microsoft include better logging during the upgrade process, as well as a rollback feature that would allow a failed upgrade to revert back to the previous OS. Until then, users and administrators should have a complete and tested backup of their system data. They should also verify their hardware against Microsoft's hardware compatibility list.

A final potential problem, for some sites at least, is that Windows 2000 is installed into the

<font size="+0">C:\Windows</font>
directory, which is the default for Windows 95. Although this might not seem like that big of a deal, new machines will probably use the
<font size="+0">C:\Winnt</font>
directory, which could cause problems for large installations, where corporate standards are important to maintaining help-desk sanity.

In my opinion, the installation should change all references from

<font 
size="+0">C:\Windows</font>
to
<font size="+0">C:\Winnt</font>
and rename the directory during the upgrade. While it is possible to manually specify the use of a directory called
<font size="+0">C:\Winnt</font>
during the installation, it is highly recommended that you not do so.

Overall, Microsoft has done a great job of providing a smooth upgrade process. On the other hand, since large companies will want to maintain control before, during, and after the upgrade, I recommend that they don't let users do it themselves. Even though the program makes it easy for a nontechnical person to perform the upgrade, it does still require some knowledge of PCs --especially if something goes wrong.

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