This post is about my biggest quandary, my biggest awkwardness, and my biggest disaster in connection with pastoral confidentiality. My biggest quandary was when someone informed me he was hiring a hit-man. I did not reveal it. Afterwards, he told me that our session had changed his mind. My biggest awkwardness was when someone revealed to me who had ransacked my vestry, and requested that I inform no one. I broke confidentiality -- a rare breach. My biggest disaster was when someone revealed massive embezzlement in a para-statal organisation, and I passed on the information. It opened a Pandora's Box of terrors.