X0306 4 2021-11-16 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001717376 Chan M.P. Eric C/O CASTLIGHT HEALTH, INC. 150 SPEAR STREET, SUITE 400 SAN FRANCISCO CA 94105 0 1 0 0 Chief Accounting Officer Class B Common Stock 2021-11-16 4 M 0 4688 0.00 A 117749 D Class B Common Stock 2021-11-16 4 M 0 1563 0.00 A 119312 D Class B Common Stock 2021-11-16 4 M 0 1875 0.00 A 121187 D Class B Common Stock 2021-11-16 4 M 0 6250 0.00 A 127437 D Class B Common Stock 2021-11-16 4 M 0 6250 0.00 A 133687 D Class B Common Stock 2021-11-17 4 S 0 7629 1.7788 D 126058 D Restricted Stock Units (RSU) 2021-11-16 4 M 0 4688 0.00 D Class B Common Stock 4688 0 D Restricted Stock Units (RSU) 2021-11-16 4 M 0 1563 0.00 D Class B Common Stock 1563 1555 D Restricted Stock Units (RSU) 2021-11-16 4 M 0 1875 0.00 D Class B Common Stock 1875 9375 D Restricted Stock Units (RSU) 2021-11-16 4 M 0 6250 0.00 D Class B Common Stock 6250 56250 D Restricted Stock Units (RSU) 2021-11-16 4 M 0 6250 0.00 D Class B Common Stock 6250 81250 D Represents the aggregate number of shares sold by the Reporting Person to cover taxes and fees due upon the release and settlement of the RSUs. The Reporting Person did not sell or otherwise dispose of any of the shares reported on this Form 4 for any reason other than to cover required taxes and fees. Represents the weighted average sales price per share. The shares sold at prices ranging from $1.76 to $1.83 per share. Full information regarding the number of shares sold at each price shall be provided upon request to the staff of the U.S. Securities and Exchange Commission, the Issuer, or a security holder of the Issuer. Each RSU represents a contingent right to receive one (1) share of the Class B Common Stock upon settlement for no consideration. 1/4th of the RSUs vested on November 16, 2018, and the remainder will vest 1/16th quarterly over three years in equal installments, subject to the continuing service of the Reporting Person on each vesting date. 1/16th of the RSUs vested on May 16, 2018, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. 1/16th of the RSUs vested on May 16, 2019, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. 1/16th of the RSUs vested on May 16, 2020, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. 1/16th of the RSUs vested on May 16, 2021, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. /s/ Mary Ahern, as attorney-in-fact 2021-11-18