Intent matters. The answer to "where do we draw the line" is that all the things you describe would be aiding and abetting if a jury would be convinced that yo

Intent matters. The answer to "where do we draw the line" is that all the things you describe would be aiding and abetting if a jury would be convinced that you did it with an intent to aid them. If you write "a general developer FAQ that would get anybody dev-minded up to speed" with the intent to help general developers everywhere and DPRK uses that, that's okay; but if you write the exact same FAQ content with an intent to help DPRK get that information because you figure out that just sending it directly in an email might be too visible, then that would be a crime, if intent can be established - based on e.g. your earlier communication and writings. It's a prohibition on trying to achieve a specific result, not on a prohibition on any particular means of achieving that result.