X0202 3 2004-06-17 0 0001106942 BLACKBOARD INC BBBB 0001292030 Pittinsky Matthew L 1899 L STREET NW 5TH FLOOR WASHINGTON DC 20036 1 1 0 0 Chairman Common Stock 418010.0000 D Series C Convertible Preferred Stock Common Stock 11.0000 D Stock Option (right to buy) 9.3400 2002-11-09 2011-05-30 Common Stock 264276.0000 D Stock Option (right to buy) 9.6600 2004-09-10 2013-09-10 Common Stock 4719.0000 D Convertible immediately and automatically converts into common stock upon the closing of the issuer's initial public offering. Includes 1 share of common stock payable with respect to accumulated dividends upon the closing of the issuer's initial public offering, assuming the issuer's initial public offering closes on June 23, 2004 at an initial price to the public of $14.00 per share. Each share of Series C Convertible Preferred Stock is convertible into approximately 0.472 shares of common stock, plus the issuance of shares of common stock in lieu of cash payment of accrued dividends thereon. The stock option vested as to 25% of the shares on 11/09/2002 and as to an additional 2.08% of the shares monthly thereafter. The stock option vests as to 25% of the shares on 09/10/2004 and as to an additional 2.08% of the shares monthly thereafter. /S/ Justin Tan, Attorney-in-fact for Matthew L Pittinsky 2004-06-17