Everyone at some stage of career, would have experienced screwing up something at work. Sometimes it go unnoticed and sometimes it makes our day worst. However, down the lane when we recollects the incident and the way we overcame it, we find ourselves a laughing stock. :P I could remember a few regarding JIRA itself.

Once I mis-mapped Issue Key in my CSV to Issue Type in JIRA while importing. JIRA created 1500+ new issue types on import and it went down. Hahaa.. However, my then lead @Vishnukumar Vasudevan was kind enough and was cool, though he knew it from the support team via logs. Luckily it was a development instance and it was brought up again. :P
There was another incident where I was writing some groovy scripts. I was referring to the JIRA java APIs navigating from google page (without noticing the version of Java doc :P). During production go-live (on an upgraded version), it started throwing lot of errors on logs since a few methods were deprecated. Somehow we fixed it sitting overnight. 
Note: Please don't share these with your current team members/managers
:P
We do not learn anything new by doing everything right! Make mistakes, learn from them, move on!! Happy Screwing-up!! 