The Outlook offline does not regiter plugin assemblies correctly. This may happen when uninstalling and re installing the Offline client.
To fix this, you need to write the Assembly Public Key token in the registery as a new key under ther "HKEY_CURRENT_USER\Software\Microsoft\MSCRMClient\AllowList" Key.
Getting the key can be done by executing sql query "select * from PluginAssemblyBase" in the organization database.
This is from KB 949088 by microsoft, can be found on KBAlertz here.
The title for the KB is :
Error message when you start a plug-in assembly in the Microsoft Dynamics CRM 4.0 client for Outlook: "Unable to load plugin assembly"
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