Sec Form 4 Filing - Gupta Neeraj @ CASTLIGHT HEALTH, INC. - 2019-11-16

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Gupta Neeraj 2. Issuer Name and Ticker or Trading Symbol CASTLIGHT HEALTH, INC. [ CSLT] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) EVP, Engineering (Last) (First) (Middle) C/O CASTLIGHT HEALTH, INC., 150 SPEAR ST., SUITE 400 3. Date of Earliest Transaction (MM/DD/YY) 11/16/2019 (Street) SAN FRANCISCO, CA94105 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Class B Common Stock 11/16/2019 M 25,000 A $ 0 353,940 D Class B Common Stock 11/16/2019 M 3,125 A $ 0 357,065 D Class B Common Stock 11/16/2019 M 8,125 A $ 0 365,190 D Class B Common Stock 11/16/2019 M 3,125 A $ 0 368,315 D Class B Common Stock 11/16/2019 M 20,750 A $ 0 389,065 D Class B Common Stock 11/18/2019 S( 1 ) 21,973 D $ 1.3442 ( 2 ) 367,092 D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Restricted Stock Units (RSU) ( 3 ) 11/16/2019 M 25,000 ( 4 ) ( 4 ) Class B Common Stock 25,000 $ 0 75,000 D Restricted Stock Units (RSU) ( 3 ) 11/16/2019( 5 ) M 3,125 ( 5 ) ( 5 ) Class B Common Stock 3,125 $ 0 15,625 D Restricted Stock Units (RSU) ( 3 ) 11/16/2019 M 8,125 ( 6 ) ( 6 ) Class B Common Stock 8,125 $ 0 73,125 D Restricted Stock Units (RSU) ( 3 ) 11/16/2019 M 3,125 ( 7 ) ( 7 ) Class B Common Stock 3,125 $ 0 34,375 D Restricted Stock Units (RSU) ( 3 ) 11/16/2019 M 20,750 ( 8 ) ( 8 ) Class B Common Stock 20,750 $ 0 269,750 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Gupta Neeraj C/O CASTLIGHT HEALTH, INC. 150 SPEAR ST., SUITE 400 SAN FRANCISCO, CA94105 EVP, Engineering Signatures /s/ Trevor Dutcher, by power of attorney 11/19/2019 Signature of Reporting Person Date

Explanation of Responses:

( 1 )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. ( 2 )Represents the weighted average sales price per share. The shares sold at prices ranging from $1.27 to $1.42 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. ( 3 )Each RSU represents a contingent right to receive one (1) share of the Class B Common Stock upon settlement for no consideration. ( 4 )1/4th of the RSUs vested on August 16, 2017, 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. ( 5 )1/4th of the RSUs vested on March 7, 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. ( 6 )1/16th of the RSUs vested on May 16, 2018, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date. ( 7 )1/16th of the RSUs vested on November 16, 2018, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date. ( 8 )1/16th of the RSUs vested on May 16, 2019, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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