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If you don't have a lot of machines you'd better just logon to each machine and update manually. Otherwise, there are a lot of ways to do it remotely and automatically. For example,

1. Use Microsoft SMS to deliver the patch.
2. Use rcmd to logon to each machine and install the patch from the command line. This can be automated.
3. Method 2 is not quite secure. A secure method would be to install ssh server on each machine and use ssh instead of rcmd. Again, this can be automated too.

You can combine method 2 and 3: use rcmd to install ssh server remotely and use ssh for security update and any future update. The only catch for method 2 and 3 is that Windows 9x/ME might not support rcmd or ssh.

A version of OpenSSH v3.0.2 on Windows can be found in the attached link.
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