IllegalAccessError:class <classname> cannot access its superinterface <interfacename>

It looks to me like package-protection fails with instrumentation and multiple classloaders, even if the loaders are chained. This javadoc on java.lang.instrument.Instrumentation isn't directly related to your scenario, but it does describe a similar scenario:

The agent should take care to ensure that the JAR does not contain any classes or resources other than those to be defined by the bootstrap class loader for the purpose of instrumentation. Failure to observe this warning could result in unexpected behaviour that is difficult to diagnose. For example, suppose there is a loader L, and L's parent for delegation is the bootstrap class loader. Furthermore, a method in class C, a class defined by L, makes reference to a non-public accessor class C$1. If the JAR file contains a class C$1 then the delegation to the bootstrap class loader will cause C$1 to be defined by the bootstrap class loader. In this example an IllegalAccessError will be thrown that may cause the application to fail. One approach to avoiding these types of issues, is to use a unique package name for the instrumentation classes.

The Java Virtual Machine Specification specifies that a subsequent attempt to resolve a symbolic reference that the Java virtual machine has previously unsuccessfully attempted to resolve always fails with the same error that was thrown as a result of the initial resolution attempt. Consequently, if the JAR file contains an entry that corresponds to a class for which the Java virtual machine has unsuccessfully attempted to resolve a reference, then subsequent attempts to resolve that reference will fail with the same error as the initial attempt.

Maybe check which loader is finding your instrumented classes, and see if there is a way to get both Assembly and IAssembly to load from that same classloader.