I am not seeking or in need of legal advice, but an interesting though experiment came to my mind.
Imagine the following situtation (I cannot really think about a concrete example and I am unsure if a real manifestation even exists): there is a free (libre) api A licensed under some permissive license or even LGPL. Non-free application B implements this api in order host plugins, but there are other free software doing the same thing. Moreover, there is plugin C acting as a plugin under api A. It links to library D, that is under GPL, so C is also under GPL. Plugins using A are loaded into hosts via a dlopen-like mechanism and use complex data structure for host-plugin communication. Neither B nor C distribute any files that may be required for A to function properly (like headers containing the structure definitions of A or dynamic libraries containing helper functions for A written by the authors of A), but such things may exist.
Now some user installs application B and plugin C on his machine, along with anything that may be required for api A to function properly. Then he proceeds and loads C into B and creates some intellectual property with B which is not a piece of software.
Did a GPL violation happend at some point, and if so, who violated GPL and why?
The authors of C violate D's license by making C possible to be used in non-free host B? This is a possibility because they can't give and exception of GPL (like one described in http://www.gnu.org/licenses/gpl-faq.html#GPLPluginsInNF or http://www.gnu.org/licenses/gpl-faq.html#LinkingOverControlledInterface) due to D's license terms.
The authors of B violate C's and D's license by making C possible to be loaded in B? This is a possibility because http://www.gnu.org/licenses/gpl-faq.html#NFUseGPLPlugins disallows the mechanisms A uses for communitation between the free and non-free modules.
The authors of A, because the api may be used (and in this case, was used) for communication between GPL'd and non-free software. This would be extremely absurd.
The user, because at the moment of loading B into C, he made a derived work of C. I think this is impossible, because he does not distribute it. But would the situation change is he decided to release a configuration file of B which makes B load C as a plugin?
Nobody, because A counts as a 'system library', and both B and C directly interact only with A, not eachother. In a sane world, this would happen...
A concrete example of A could be some kind of audio (think LADSPA) or image processing api. However, I could find no such interface (that is free software, generic and is also implemented by commercial tools). A real-world example could also be quite enlightening.