X0306 4 2019-07-26 0 0001446847 IRONWOOD PHARMACEUTICALS INC IRWD 0001601360 Gilbert Halley E C/O IRONWOOD PHARMACEUTICALS, INC. 301 BINNEY STREET CAMBRIDGE MA 02142 0 1 0 0 Chief Admin Officer & SVP Class A Common Stock 2019-07-26 4 M 0 20000 4.88 A 260169 D Class A Common Stock 2019-07-26 4 S 0 20000 10.00 D 240169 D Employee Stock Option (Right to Buy) 4.88 2019-07-26 4 M 0 20000 4.88 D 2019-07-28 Class A Common Stock 20000 22472 D The reporting person acquired 1,929 shares of Class A common stock under the issuer's employee stock purchase plan on June 28, 2019. This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $9.80 to $10.09, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote. The option vested as to 20,000 shares of Class A Common Stock upon the issuer's achievement of a commercial milestone on January 4, 2017. The remainder of the option expired on July 28, 2019. /s/ Conor Kilroy, Attorney-in-Fact 2019-07-30