“I set up a twitter bot that thanked trolls for insulting our company.”

This one happened years ago at a SaaS startup with about 100 employees trying to make waves in the productivity software space. We had just launched a new feature and expected social media to blow up with customer praise. To save time and keep the momentum going, we set up a Twitter bot to automatically respond to positive mentions. The idea was simple: if someone said something like “This tool is amazing!” the bot would reply, “Thanks for your support! We’re glad you’re loving it!”

What we didn’t anticipate was how easily the automation could be exploited. Within hours, trolls caught on and started tagging us with sarcastic or offensive posts: “This company is a scam and a joke!” The bot, unaware of context, chirped back, “Thanks for your support!”

People started posting screenshots of the replies. Some posts racked up thousands of likes and shares, and our boss was not amused. We had to shut the bot down, issue an apology, and manually reply to comments for weeks. PR nightmare.