They can just block everything by default and only enable what they can decrypt. Maybe you could try tunelling encrypted data over HTTP, but heuristics could probably pick that up too.
This realistically shouldn't be too hard to do with obfsproxy's already-built framework.
s/cat pictures/whatever you want/
For email, you'd encrypt data to have it look like regular prose. So you'd only get a few bits per English word, but that would be sufficient for short messages. Could also make use of extra spaces in between words.
The real trick with that would be to take an existing document, and alter it to encode a message. So you'd be doing things like using synonym choice to get your bits.