In December, job recruiter J-Com's IPO in Tokyo goes awry when a trader for Mizuho Securities types in an order to sell 610,000 shares at 1 yen (less than a penny) per share instead of the intended 1 share at 610,000 yen (about $5,000). Though the order is for 41 times the number of outstanding shares, the Tokyo Stock Exchange insists that the order be processed as entered. Mizuho loses at least 27 billion yen ($225 million) on the typo, an amount nearly equal to its entire profit for the prior fiscal year.

Oh, wait...wrong text box...d'oh!

Update: This one highlights the importance of double-checking your boolean logic:

A few weeks after eZiba.com sends out its winter catalog, the call center's pin-drop silence begins to worry execs. As it turns out, a bug in a program designed to identify the best prospects on eZiba's mailing list led to the catalog instead being sent to those deemed least likely to respond. "Sadly, our probability estimates were correct," says eZiba founder Dick Sabot. On Jan. 14, eZiba suspends operations while seeking new investors to cover its cash shortfall. Overstock.com later buys the retailer's assets for $500,000.

Ouch.