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 OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

Nolan Mangini Siobhan 		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)
CFO & Treasurer
(Last)          (First)          (Middle)

C/O CASTLIGHT HEALTH, INC., 150 SPEAR ST., SUITE 400 		3. Date of Earliest Transaction (MM/DD/YYYY)

5/16/2019
(Street)

SAN FRANCISCO, CA 94105
(City)        (State)        (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)

 
6. Individual or Joint/Group Filing (Check Applicable Line)

_ X _ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3) 		2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. 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   5/16/2019     M (1)    2500   A $0   241581   D    
Class B Common Stock   5/16/2019     M (2)    1875   A $0   243456   D    
Class B Common Stock   5/16/2019     M (3)    15625   A $0   259081   D    
Class B Common Stock   5/16/2019     M (4)    6250   A $0   265331   D    
Class B Common Stock   5/16/2019     M (5)    11250   A $0   276581   D    
Class B Common Stock   5/16/2019     M (6)    23062   A $0   299643   D    
Class B Common Stock   5/17/2019     S    21756   (7) D $3.4194   (8) 277887   D    

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3) 		2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. 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 7. Title and Amount of Securities Underlying Derivative Security
(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   $0   (9) 5/16/2019     M   (1)       2500      (10)   (10) Class B Common Stock   2500   $0   5000   D    
Restricted Stock Units   $0   (9) 5/16/2019     M   (2)       1875      (11)   (11) Class B Common Stock   1875   $0   5625   D    
Restricted Stock Units   $0   (9) 5/16/2019     M   (3)       15625      (12)   (12) Class B Common Stock   15625   $0   78125   D    
Restricted Stock Units   $0   (9) 5/16/2019     M   (4)       6250      (13)   (13) Class B Common Stock   6250   $0   43750   D    
Restricted Stock Units   $0   (9) 5/16/2019     M   (5)       11250      (14)   (14) Class B Common Stock   11250   $0   123750   D    
Restricted Stock Units   $0   (9) 5/16/2019     M   (6)       23062      (15)   (15) Class B Common Stock   23062   $0   345938   D    

Explanation of Responses:
(1)  Release and settlement of restricted stock units ("RSUs") granted to the Reporting Person on November 16, 2015, the grant of which was previously reported by the Reporting Person on a Form 3.
(2)  Release and settlement of RSUs granted to the Reporting Person on February 26, 2016, the grant of which was previously reported by the Reporting Person on a Form 3.
(3)  Release and settlement of RSUs granted to the Reporting Person on July 8, 2016, the grant of which was previously reported by the Reporting Person on a Form 4.
(4)  Release and settlement of RSUs granted to the Reporting Person on March 7, 2017, the grant of which was previously reported by the Reporting Person on a Form 4.
(5)  Release and settlement of RSUs granted to the Reporting Person on February 15, 2018, the grant of which was previously reported by the Reporting Person on a Form 4.
(6)  Release and settlement of RSUs granted to the Reporting Person on April 5, 2019, the grant of which was previously reported by the Reporting Person on a Form 4.
(7)  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.
(8)  Represents the weighted average sales price per share. The shares sold at prices ranging from $3.27 to $3.53 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.
(9)  Each RSU represents a contingent right to receive 1 share of the Issuer's Class B common stock upon settlement for no consideration.
(10)  25% of the RSUs vested on November 16, 2016 and the remainder vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.
(11)  25% of the RSUs vested on February 16, 2017 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.
(12)  25% of the RSUs vested on August 16, 2017 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.
(13)  25% of the RSUs will vest on February 16, 2018 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.
(14)  The RSUs will vest in equal quarterly installments over four years, beginning on May 16, 2018. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.
(15)  The RSUs will vest in equal quarterly installments over four years, beginning on May 16,2019. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
Nolan Mangini Siobhan
C/O CASTLIGHT HEALTH, INC.
150 SPEAR ST., SUITE 400
SAN FRANCISCO, CA 94105

CFO & Treasurer

Signatures
/s/ Jennifer Chaloemtiarana, by power of attorney 5/20/2019
** Signature of Reporting Person 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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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