I wrote a ruby script to manage the dependencies, so that I can get the order of the plugins right. I've since written a powershell script to download the latest version of each of the plugins, so I've worked around this issue.
My workflow for updating plugins is a bit convoluted, I have a Jenkins installation on my personal laptop, and use it to grab the desired plugins and updates. I then run the ruby script to list the plugins in order of dependency. I email that list to my work address. From my work laptop, I feed the list to the powershell script that grabs the packages from the Jenkins plugins site. I transfer the lot to the server, and load them manually from the plugins page. Woe is me if I try to dump all the packages directly in the plugins directory and restart.
I tried loading them via a Groovy script from the Jenkins console, but although dynamic loading appeared to work, items I loaded earlier weren't recognized even though I'd restart when I got an exception saying a restart was needed.
I'd be very happy to hear of a better way to update plugins (given the server doesn't have an Internet connection).
Why hide the most current version of the plugin? What's the now preferred way of getting a new plugin?