Hi,
Version 2.2.8.1 is very old. It is quite possible it had a bug running under medium trust.
I would suggest:
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review the release notes of all version since 2.2.8.1 for any upgrade notes
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make sure .NET 3.5 SP1 is on both machines
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backup everything on the Win 2008 machine so you can restore to your current state if something goes wrong
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upgrade the win 2008 machine to the latest version 2.3.3.4.
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add the ScriptLoader control to your layout.Master if it does not already have it, copy from one of the skins under /Data/skins in the new version
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make sure everything is working ok, if you have any issues post in the forums
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Then try the migration again
Hope it helps,
Joe