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The error was entirely on my part and completely unrelated. Sorry for the noise.

The cause of this issue was pretty bizzare and I'll explain below for those interested, but TL;DR is there's nothing wrong with askbot or jinja2_makemessages. So the django version thing that Evgeny mentions must be unrelated.

Being new to django and rosetta, I completely missed the fact that you have to select a 3rd party catalogue for translation (top-right corner of the initial rosetta view, not visible in later views; defaults to "Project only").

The reason this sort of worked for us and we didn't notice anything for a long time was that because of django.staticfiles, most of the askbot strings were actually picked up for translation! managy.py collectstatic copied askbot templates to a local dir under project, where makemessages found them and presented them for translation in rosetta. So when we were thinking we're translating askbot, we were actually translating its (partially) cloned version in STATIC_DIR! Heh.