@thegibson Long ago, I created a website with a webmaster email address on it that forwarded to my boss. Then one day my boss went on vacation, so he set up an autoresponder. Someone mailed the webmaster, it forwarded to the boss, which replied to the webmaster... Which forwarded to the.boss. And I brought down the company mail for a while.

Not my worst fail though. My worst was owning the component that brought down healthcare.gov when it launched. Oops.