I usually separate them into two separate assemblies. One of the usual reasons for a interface is to have a series of objects look the same to some subsystem of your software. For example I have all my Reports implementing the IReport Interfaces. IReport is used is not only used in printing but for previewing and selecting individual options for each report. Finally I have a collection of IReport to use in dialog where the user selects which reports (and configuring options) they want to print.
The Reports reside in a separate assembly and the IReport, the Preview engine, print engine, report selections reside in their respective core assembly and/or UI assembly.
If you use the Factory Class to return a list of available reports in the report assembly then updating the software with new report becomes merely a matter of copying the new report assembly over the original. You can even use the Reflection API to just scan the list of assemblies for any Report Factories and build your list of Reports that way.
You can apply this techniques to Files as well. My own software runs a metal cutting machine so we use this idea for the shape and fitting libraries we sell alongside our software.
Again the classes implementing a core interface should reside in a separate assembly so you can update that separately from the rest of the software.