Today Yahoo! News’s official Twitter feed felt the wrath of an easily offended internet.

The company debuted the #HashOut tag to promote their upcoming “social media talk show” of the same name with a message making light of the recent two-year jail sentence handed down to Russian anti-government punk bad Pussy Riot. Yahoo! tweeted:

“Last week, a Moscow judge sentenced a punk band to two years in prison. What musical act would you send to lockup, and why?”

We guess we can see why they thought this one would work: Everybody has opinions about music, everybody read something about Pussy Riot last week, and everybody likes to be interactive. But Yahoo!’s opening shot fell a bit short: While a few angry re-tweeters noted that the suppression of free speech by authoritarian governments is no laughing matter, we just didn’t think the “joke” was very funny.

Cheeky humor usually wins the day online, but the question must be asked: Where does the invisible line between “edgy” and “offensive” begin? Are the rules different in the social media sphere, particularly when the responsible party is a huge corporation rather than a single individual? Most importantly, since social media is all about standing out, how can marketers and PR reps achieve and maintain a winning balance between risky and boring?

We understand a general aversion to risk, but “safe” comedy gets dull pretty quickly, right Kenny?