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That I know of, Microsoft Paint does not have the ability set transparencies for pictures that can support it. There's always Gimp for worktstations that can and ARE PERMISABLE to install.

Two situations I find myself in quite frequently is a) I'm ssh'd into a linux box where anything gui is not possible or b) in a windows server box where our policies do not permit installing anything on production servers other than what they were inteded for (yes, even Gimp is not allowed). Is there some back door way of accomplishing this task?

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Hell yes. On Linux, with graphicsmagick or imagemagick, anything is possible! But I don't use them really often, so you will need to wait a few minutes until someone posts a detailed howto. :) –  Shiki Aug 3 '12 at 21:30
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You ca use imagemagick as suggested above.

convert input.png -channel Alpha -evaluate Divide 2 output.png

This command will change the transparency of the whole picture (-channel Alpha) to 50% (Divide 2)

You can use "-transparent white" instead of "-channel Alpha" to change the transparency of the white color only.

There are plenty of other options, like changing the transparency of only one color etc.

You can use this on several image formats.

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Of course this answers only the linux part of your question. For windows, connect via ssh to a linux box, convert the image and transfer it back. –  Bruno9779 Aug 4 '12 at 5:34
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