CSLT / Castlight Health Inc - Class B - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Castlight Health Inc - Class B
US ˙ NYSE ˙ US14862Q1004
HINDI NA ACTIVE ANG SIMBONG ITO

Mga Batayang Estadistika
LEI 549300K52FAO83JL0L06
CIK 1433714
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Castlight Health Inc - Class B
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
February 28, 2022 15-12B

As filed with the Securities and Exchange Commission on February 28, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EX

As filed with the Securities and Exchange Commission on February 28, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 SC TO-T/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3) CASTLIGHT HEALTH, INC. (Name of Subject Company (Is

SC TO-T/A 1 d508987dsctota.htm SC TO-T/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3) CASTLIGHT HEALTH, INC. (Name of Subject Company (Issuer)) CARBON MERGER SUB, INC. (Offeror) A wholly owned subsidiary of VERA WHOLE HEALTH, INC. (Parent of Offe

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 EX-99.1

Vera Whole Health, Inc. Completes Acquisition of Castlight Health, Inc.

FOR IMMEDIATE RELEASE Vera Whole Health, Inc. Completes Acquisition of Castlight Health, Inc. SEATTLE, WA - Feb. 17, 2022 - Vera Whole Health, Inc. (?Vera?) announced today that it has successfully completed its previously announced acquisition of Castlight Health, Inc. (?Castlight?) at a price of $2.05 per share, net to the seller, in cash, without interest and subject to any required tax withhol

February 17, 2022 EX-99.25

EX-99.25

NOTIFICATION OF THE REMOVAL FROM LISTING AND REGISTRATION OF THE STATED SECURITIES The New York Stock Exchange hereby notifies the SEC of its intention to remove the entire class of the stated securities from listing and registration on the Exchange at the opening of business on February 28, 2022, pursuant to the provisions of Rule 12d2-2 (a).

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 8-K

Changes in Control of Registrant, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 16, 2022 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

As filed with the Securities and Exchange Commission on February 17, 2022 Registration No.

February 17, 2022 EX-3.2

Amended and Restated Bylaws of Castlight Health, Inc.

CASTLIGHT HEALTH, INC. THIRD AMENDED AND RESTATED BYLAWS As Adopted on February 17, 2022 CASTLIGHT HEALTH, INC. THIRD AMENDED AND RESTATED BYLAWS Table of Contents Page Article I MEETINGS OF STOCKHOLDERS 1 Section 1.01. Annual Meetings 1 Section 1.02. Special Meetings 1 Section 1.03. Participation in Meetings by Remote Communication 1 Section 1.04. Notice of Meetings; Waiver of Notice 1 Section 1.

February 17, 2022 EX-3.1

Amended and Restated Certificate of Incorporation of Castlight Health, Inc.

AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF CASTLIGHT HEALTH, INC. ARTICLE I: NAME The name of the corporation is Castlight Health, Inc. (hereinafter the ?Corporation?). ARTICLE II: AGENT FOR SERVICE OF PROCESS The address of the Corporation?s registered office in the State of Delaware is located at 1209 Orange Street, Corporation Trust Center, in the City of Wilmington, County of New Cas

February 17, 2022 EX-99.(A)(5)(D)

Press Release issued by Vera Whole Health, Inc., dated February 17, 2022.

Exhibit (a)(5)(D) FOR IMMEDIATE RELEASE Vera Whole Health, Inc. Announces Completion of the Tender Offer for All Outstanding Shares of Castlight Health, Inc. SEATTLE, WA - Feb. 17, 2022 - Vera Whole Health, Inc. (?Vera?) announced today that its wholly-owned subsidiary, Carbon Merger Sub, Inc. (?Purchaser?), has successfully completed the previously announced cash tender offer for all of the issue

February 17, 2022 S-8 POS

As filed with the Securities and Exchange Commission on February 17, 2022

S-8 POS 1 s-8pos.htm S-8 POS As filed with the Securities and Exchange Commission on February 17, 2022 Registration No. 333-194566 Registration No. 333-202701 Registration No. 333-216374 Registration No. 333-221191 Registration No. 333-223373 Registration No. 333-230026 Registration No. 333-236778 Registration No. 333-248586 Registration No. 333-253453 UNITED STATES SECURITIES AND EXCHANGE COMMISS

February 17, 2022 SC 14D9/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 (Amendment No. 3) Castlight Health, Inc. (Name o

SC 14D9/A 1 d317899dsc14d9a.htm SC 14D9/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 (Amendment No. 3) Castlight Health, Inc. (Name of Subject Company) Castlight Health, Inc. (Name of Person(s) Filing Statement) Class A Common Stock, par val

February 14, 2022 EX-99.B

Power of Attorney

EXHIBIT B Power of Attorney KNOW ALL MEN BY THESE PRESENTS, that I, Lee S. Ainslie III, hereby make, constitute and appoint Mark Gurevich as my agent and attorney-in -fact for the purpose of executing (i) in my personal capacity or (ii) in my capacity as manager or other officer or representative of Maverick Capital Management, LLC, Maverick Capital, Ltd. or any affiliate of either, all documents

February 14, 2022 SC 13G/A

CSLT / Castlight Health Inc / MAVERICK CAPITAL LTD - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 9)* CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

February 14, 2022 EX-99.A

JOINT FILING AGREEMENT

EXHIBIT A JOINT FILING AGREEMENT The undersigned hereby agree that the statement on Schedule 13G/A with respect to the Common Stock of Castlight Health, Inc.

February 9, 2022 EX-99.(A)(5)(C)

E-mail to employees of Vera Whole Health, Inc., dated February 9, 2022.

Exhibit (a)(5)(C) From: Ryan Schmid To: All Vera Subject: Update on our journey forward with Castlight Team, I hope you were able to join our most recent Team Esteem to hear directly from me and Maeve O?Meara, Castlight?s CEO, discussing our excitement as we take the next step in our journey towards a health revolution by combining our two organizations.

February 9, 2022 SC TO-T/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2) CASTLIGHT HEALTH, INC. (Name of Subject Company (Is

SC TO-T/A 1 d294730dsctota.htm SC TO-T/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2) CASTLIGHT HEALTH, INC. (Name of Subject Company (Issuer)) CARBON MERGER SUB, INC. (Offeror) A wholly owned subsidiary of VERA WHOLE HEALTH, INC. (Parent of Offe

February 7, 2022 SC 14D9/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 (Amendment No. 2) Castlight Health, Inc. (Name o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 (Amendment No. 2) Castlight Health, Inc. (Name of Subject Company) Castlight Health, Inc. (Name of Person(s) Filing Statement) Class A Common Stock, par value $0.0001 per share Class B Common Stock,

February 4, 2022 SC TO-T/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(D)(1) OR 13(E)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) CASTLIGHT HEALTH, INC. (Name of Subject Company (Is

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(D)(1) OR 13(E)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) CASTLIGHT HEALTH, INC. (Name of Subject Company (Issuer)) CARBON MERGER SUB, INC. (Offeror) A wholly owned subsidiary of VERA WHOLE HEALTH, INC. (Parent of Offeror) TRUTH HOLDINGS MIDCO, INC. TRUTH HOL

February 4, 2022 SC 14D9/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 (Amendment No. 1) Castlight Health, Inc. (Name o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 (Amendment No. 1) Castlight Health, Inc. (Name of Subject Company) Castlight Health, Inc. (Name of Person(s) Filing Statement) Class A Common Stock, par value $0.0001 per share Class B Common Stock,

January 24, 2022 SC 13G/A

CSLT / Castlight Health Inc / Gagnon Neil - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to desig

January 19, 2022 EX-99.(A)(1)(F)

Notice of Offer to Purchase for Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock Castlight Health, Inc. $2.05 Net Per Share Carbon Merger Sub, Inc. a wholly owned subsidiary of Vera Whole Health, Inc.

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(1)(f) This announcement is neither an offer to purchase nor a solicitation of an offer to sell Shares (as defined below). The Offer (as defined below) is made solely pursuant to the Offer to Purchase (as defined below), dated January 19, 2022, and the related Letter of Transmittal (as defined below) together with any amendments or supplements thereto. T

January 19, 2022 SC 14D9

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 Castlight Health, Inc. (Name of Subject Company)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 Castlight Health, Inc. (Name of Subject Company) Castlight Health, Inc. (Name of Person(s) Filing Statement) Class A Common Stock, par value $0.0001 per share Class B Common Stock,

January 19, 2022 SC TO-T

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 CASTLIGHT HEALTH, INC. (Name of Subject Company (Issuer)) CARBON MERGER SUB, INC. (Offeror) A wholly owned subsidiary of VERA WHOLE HEALTH, INC. (Parent of Offeror) TRUTH HOLDINGS MIDCO, INC. TRUTH HOLDINGS TOPCO, INC.

January 19, 2022 EX-99.(D)(3)

Non-Disclosure Agreement between Castlight Health, Inc. and Clayton, Dubilier & Rice, LLC, dated May 11, 2021.*

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(d)(3) May 11, 2021 CONFIDENTIAL Clayton, Dubilier & Rice, LLC 375 Park Avenue, 18th Floor New York, NY 10152 Ladies and Gentlemen: In connection with the consideration of a possible negotiated transaction between Clayton, Dubilier & Rice, LLC (?CD&R? or ?you?) or one or more of its affiliates, and Castlight Health Inc., a Delaware corporation (the ?Company

January 19, 2022 EX-99.(A)(1)(A)

Offer to Purchase for Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 Net Per Share by CARBON MERGER SUB, INC., a wholly owned subsidiary of VERA WHOLE HEALTH, INC. THE OFFER AND WITHDRA

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(1)(a) Offer to Purchase for Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 Net Per Share by CARBON MERGER SUB, INC., a wholly owned subsidiary of VERA WHOLE HEALTH, INC. THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MINUTE AFTER 11:59 P.M., NEW YORK CITY TIME, ON FEBRUARY 16, 2022, UN

January 19, 2022 EX-99.(A)(1)(E)

Offer To Purchase For Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 NET PER SHARE Pursuant to the Offer to Purchase dated January 19, 2022 by CARBON MERGER SUB, INC., a wholly owned su

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(1)(e) Offer To Purchase For Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 NET PER SHARE Pursuant to the Offer to Purchase dated January 19, 2022 by CARBON MERGER SUB, INC., a wholly owned subsidiary of VERA WHOLE HEALTH, INC. THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MINUTE AFTER

January 19, 2022 EX-99.(A)(1)(C)

NOTICE OF GUARANTEED DELIVERY For Tender of Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. $2.05 NET PER SHARE Pursuant to the Offer to Purchase dated January [19], 2022 by CARBON MERGER SUB, INC., an wholly-owned s

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(1)(c) ?NOTICE OF GUARANTEED DELIVERY For Tender of Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC.? at $2.05 NET PER SHARE? Pursuant to the Offer to Purchase dated January [19], 2022 by CARBON MERGER SUB, INC.,? an wholly-owned subsidiary of VERA WHOLE HEALTH, INC.? THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MIN

January 19, 2022 EX-99.(A)(1)(D)

Offer To Purchase For Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. $2.05 NET PER SHARE Pursuant to the Offer to Purchase dated January 19, 2022 CARBON MERGER SUB, INC. a wholly owned subsidiar

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(1)(d) Offer To Purchase For Cash All Outstanding Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 NET PER SHARE Pursuant to the Offer to Purchase dated January 19, 2022 by CARBON MERGER SUB, INC. a wholly owned subsidiary of VERA WHOLE HEALTH, INC. THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MINUTE AFTER

January 19, 2022 EX-99.(A)(5)(B)

Press Release issued by Vera Whole Health, Inc., dated January 19, 2022.*

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(5)(B) FOR IMMEDIATE RELEASE Vera Whole Health, Inc. Announces Commencement of the Tender Offer for All Outstanding Shares of Castlight Health, Inc. NEW YORK, NY ? January 19, 2022 ? Vera Whole Health, Inc. (?Parent?, and together with its consolidated subsidiaries ?Vera?) announced today that its affiliate, Carbon Merger Sub, Inc., (?Purchaser?), commen

January 19, 2022 EX-99.(A)(1)(B)

Letter of Transmittal to Tender Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 Net Per Share Pursuant to the Offer to Purchase, dated January 19, 2022 by CARBON MERGER SUB, INC., a wholly owned subsidiary o

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(a)(1)(b) Letter of Transmittal to Tender Shares of Class A Common Stock and Class B Common Stock of CASTLIGHT HEALTH, INC. at $2.05 Net Per Share Pursuant to the Offer to Purchase, dated January 19, 2022 by CARBON MERGER SUB, INC., a wholly owned subsidiary of VERA WHOLE HEALTH, INC. The undersigned represents that I (we) have full authority to surrender w

January 19, 2022 EX-99.(B)(1)

Equity Commitment Letter, dated January 4, 2022 from Clayton, Dubilier & Rice Fund XI, L.P. and accepted and agreed to by Vera Whole Health, Inc.*

CASTLIGHT HEALTH, INC. SC TO-T Exhibit 99(b)(1) January 4, 2022 To: Vera Whole Health, Inc. 1201 Second Ave, Suite 1400 Seattle, WA 98101 Commitment Letter (the ?Commitment Letter?) Ladies and Gentlemen: Reference is made to the Agreement and Plan of Merger, dated as of the date hereof (as the same may be amended, supplemented or otherwise modified from time to time, the ?Merger Agreement?), by an

January 6, 2022 EX-99.(A)(5)(B)

E-mail to employees of Vera Whole Health, Inc., dated January 5, 2022.

Exhibit (a)(5)(B) Vera employee message Date: Wednesday, Jan 5, 5:40 am PST From: Ryan Schmid To: Vera All Subject: The next step in our journey towards a health revolution Team, I?m excited to share with you that Vera Whole Health will combine with Castlight Health, a pioneering healthcare data and navigation company.

January 6, 2022 EX-99.(A)(5)(D)

Blog post of Vera Whole Health, Inc., dated January 5, 2022.

Exhibit (a)(5)(D) Castlight Health and Vera Whole Health to Combine, Creating Pioneer Company to Scale Value Based Care in Commercial Market By Vera Whole Health | Posted January 5, 2022 | Posted in News Castlight Health and Vera Whole Health are combining to scale value-based care within the Commercial Market.

January 6, 2022 EX-99.(A)(5)(E)

Social Media (Twitter and Linkedin) Posts of Vera Whole Health, Inc., dated January 5, 2022.

Exhibit (a)(5)(E) The following was posted by Vera on Twitter at https://twitter.com/verawholehealth/status/1478851049574313988 on January 5, 2022. The following was posted by Vera on Twitter at https://twitter.com/verawholehealth/status/1478805829369442306 on January 5, 2022. 2 The following was posted by Vera on Linkedin at https://www.linkedin.com/posts/verawholehealthcastlight-health-and-vera-

January 6, 2022 SC TO-C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 Castlight Health, Inc. (Name of Subject Company (Issuer)) Carbon Merg

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 Castlight Health, Inc. (Name of Subject Company (Issuer)) Carbon Merger Sub, Inc. (Name of Filing Person?Offeror) Vera Whole Health, Inc. Truth Holdings Midco, Inc. Truth Holdings Topco, Inc. Truth Holdings, L.P. Truth

January 6, 2022 EX-99.(A)(5)(C)

E-mail to prospective clients of Vera Whole Health, Inc., dated January 5, 2022.

Exhibit (a)(5)(C) Subject: Castlight Health and Vera Whole Health to Combine, Creating Pioneer Company to Scale Value Based Care in Commercial Market.

January 5, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 4, 2022 CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

January 5, 2022 EX-99.1

Castlight Health and Vera Whole Health to Combine to Pioneer and Scale Value-Based Care in Commercial Market

Exhibit 99.1 Castlight Health and Vera Whole Health to Combine to Pioneer and Scale Value-Based Care in Commercial Market ? Combined company will integrate Castlight?s market-leading navigation technology with Vera?s best in class advanced primary care model to expand access to care, reduce healthcare costs, and improve outcomes ? Clayton, Dubilier & Rice funds to invest in new enterprise; former

January 5, 2022 EX-99.2

Email for All Employees Following Announcement

Exhibit 99.2 Email for All Employees Following Announcement From: Maeve O?Meara Subject: Exciting News! Team, I hope you all had a restful break and enjoyed some time with your family, friends, and loved ones. When I stepped into the CEO role in July of 2019, I shared my belief that our unique advantage was the combination of our data and technology. I laid out a strategy to unleash greater value

January 5, 2022 EX-10.1

Form of Tender and Support Agreement, dated as of January 4, 2022, by and among Vera Whole Health, Inc., Carbon Merger Sub, Inc., and the stockholders party thereto (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed with the SEC by Castlight Health, Inc. on January 5, 2022).*

Exhibit 10.1 TENDER AND SUPPORT AGREEMENT This TENDER AND SUPPORT AGREEMENT (this ?Agreement?) dated as of January [?], 2022, is by and among Vera Whole Health, Inc., a Delaware corporation (?Parent?), Carbon Merger Sub, Inc., a Delaware corporation and a wholly-owned subsidiary of Parent (?Merger Sub? and together with Parent, the ?Buyer Parties?), and each of the stockholders of Castlight Health

January 5, 2022 EX-2.1

Agreement and Plan of Merger, dated January 4, 2022, by and among Vera Whole Health, Inc., Carbon Merger Sub, Inc. and Castlight Health, Inc. (incorporated by reference to Exhibit 2.1 to the Current Report on Form 8-K filed with the SEC by Castlight Health, Inc. on January 5, 2022).*

Exhibit 2.1 AGREEMENT AND PLAN OF MERGER by and among VERA WHOLE HEALTH, INC., CARBON MERGER SUB, INC., and CASTLIGHT HEALTH, INC. Dated as of January 4, 2022 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS & INTERPRETATIONS 3 1.1 Certain Definitions 3 1.2 Additional Definitions 16 1.3 Certain Interpretations 18 ARTICLE II THE TRANSACTIONS 20 2.1 The Offer 20 2.2 Additional Actions 23 2.3 Stockholder

January 5, 2022 EX-99.3

2

Exhibit 99.3 Social Media Content LinkedIn post, dated January 5, 2022 (https://www.linkedin.com/company/castlight-health) We are thrilled to announce that we have entered into a definitive agreement to combine with @verawholehealth, creating a new company to pioneer and scale value-based care in commercial markets! The combination of Castlight?s market-leading navigation technology with Vera?s be

January 5, 2022 EX-99.1

1

Exhibit 99.1 The Summary: Today?s News ? Castlight has signed an agreement to combine with Vera Whole Health, a privately held leading advanced primary care organization. The companies will combine to create a first-of-its-kind, purpose-built primary care platform that will seek to transform how patients access and experience the healthcare system. ? The combined company will be a private company

January 5, 2022 SC14D9C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 Castlight Health, Inc. (Name of Subject Company)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14D-9 (Rule 14d-101) Solicitation/Recommendation Statement under Section 14(d)(4) of the Securities Exchange Act of 1934 Castlight Health, Inc. (Name of Subject Company) Castlight Health, Inc. (Name of Person(s) Filing Statement) Class A Common Stock, par value $0.0001 per share Class B Common Stock, par value $0.0001

November 15, 2021 SC 13G/A

CSLT / Castlight Health Inc / WELLCOME TRUST LTD (THE) as trustee of the WELLCOME TRUST - SC 13G/A Passive Investment

SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (Amendment No. 4)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) November 15, 2

November 3, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ☐ TRANSITION REPORT PURSUANT

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-3633

November 2, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 2, 2021 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

November 2, 2021 EX-99.1

Castlight Health Announces Third Quarter 2021 Results Third Straight Quarter of Sequential ARR Growth

Castlight Health Announces Third Quarter 2021 Results Third Straight Quarter of Sequential ARR Growth SAN FRANCISCO - November 2, 2021 - Castlight Health, Inc.

August 4, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 ☐ TRANSITION REPORT PURSUANT TO S

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CAS

August 3, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 3, 2021 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission Fi

August 3, 2021 EX-99.1

Castlight Health Announces Second Quarter 2021 Results Company Demonstrates Sequential Increase in ARR

Castlight Health Announces Second Quarter 2021 Results Company Demonstrates Sequential Increase in ARR SAN FRANCISCO - August 3, 2021 - Castlight Health, Inc.

June 10, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 10, 2021 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission Fil

April 30, 2021 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CA

April 30, 2021 EX-10.1

Consulting Agreement, dated as of February 16, 2021, by and between the Registrant and Seth Cohen

Consulting Services Agreement Dear Seth: I am pleased to formalize your role as a consultant (?You? or ?Consultant?) to Castlight Health, Inc.

April 29, 2021 EX-99.1

Castlight Health Announces First Quarter 2021 Results Company Demonstrates Sequential Increase in ARR and Increases 2021 Outlook

Castlight Health Announces First Quarter 2021 Results Company Demonstrates Sequential Increase in ARR and Increases 2021 Outlook SAN FRANCISCO - April 29, 2021 - Castlight Health, Inc.

April 29, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 29, 2021 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission Fi

April 20, 2021 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 20, 2021 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 5, 2021 SC 13D/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 4)1 C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 4)1 Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 (Title of Class of Securities) 14862Q 10 0 (CUSIP Number) Steve Wolosky

February 26, 2021 SC 13D/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 3)1 C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 3)1 Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 (Title of Class of Securities) 14862Q 10 0 (CUSIP Number) Steve Wolosky

February 24, 2021 S-8

- S-8

As filed with the Securities and Exchange Commission on February 24, 2021 Registration No.

February 24, 2021 EX-4.3

Description of Castlight Health, Inc. Common Stock Registered under Section 12 of the Securities Exchange Act of 1934.

Exhibit 4.3 Description of the Registrant?s Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934 The following description of capital stock of Castlight Health, Inc. (the ?company,? ?we,? ?us? and ?our?) summarizes certain provisions of our restated certificate of incorporation and our amended and restated bylaws. The description is intended as a summary, and is qual

February 24, 2021 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Subsidiaries of Castlight Health, Inc. Name of Subsidiary Jurisdiction Engage Technologies, Inc. Delaware Jiff, Inc. Delaware

February 24, 2021 10-K

Annual Report - 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the year ended December 31, 2020 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CASTLIGHT HEAL

February 23, 2021 EX-99.1

Castlight Health Announces Fourth Quarter and Full Year 2020 Results

Castlight Health Announces Fourth Quarter and Full Year 2020 Results SAN FRANCISCO - February 23, 2021 - Castlight Health, Inc.

February 23, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 23, 2021 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

February 16, 2021 SC 13G/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 8)* CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Cl

SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 8)* CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate b

February 9, 2021 SC 13G/A

SIGNATURE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to desig

February 4, 2021 SC 13D/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 2)1 C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 2)1 Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 (Title of Class of Securities) 14862Q 10 0 (CUSIP Number) Steve Wolosky

January 15, 2021 SC 13G/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (Amendment No. 3)* Castlight Health, I

SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (Amendment No. 3)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2

December 21, 2020 8-K

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 December 18, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

December 21, 2020 EX-3.1

Second Amended and Restated Bylaws, as amended December 18, 2020

CASTLIGHT HEALTH, INC. (a Delaware corporation) SECOND AMENDED AND RESTATED BYLAWS As Adopted March 19, 2014 Amended and Restated on December 18, 2020 CASTLIGHT HEALTH, INC. (a Delaware corporation) SECOND AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Page Article I: STOCKHOLDERS 1 Section: 1.1: Annual Meetings 1 Section: 1.2: Special Meeting 1 Section: 1.3: Notice of Meetings 1 Section: 1.4: Adjo

December 21, 2020 EX-3.2

Second Amended and Restated Bylaws of Castlight Health, Inc., effective December 18, 2020 (marked for changes

CASTLIGHT HEALTH, INC. (a Delaware corporation) SECOND AMENDED AND RESTATED BYLAWS As Adopted March 19, 2014 Amended and Restated on December 18, 2020 CASTLIGHT HEALTH, INC. (a Delaware corporation) SECOND AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Page ArticleARTICLE I -: STOCKHOLDERS......................................................................… 1 Section: 1.1: Annual Meetings........

November 6, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-3633

November 5, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 5, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

November 5, 2020 EX-99.1

Castlight Health Announces Third Quarter 2020 Results

Castlight Health Announces Third Quarter 2020 Results SAN FRANCISCO - November 5, 2020 - Castlight Health, Inc.

September 3, 2020 EX-99.1

Form of Inducement Restricted Stock Unit Agreement

Notice of Restricted Stock Unit Award Castlight Health, Inc. You (“you”) have been granted an award of Restricted Stock Units (“RSUs”) by Castlight Health, Inc. (the “Company”) subject to the terms and conditions of this Notice of Restricted Stock Unit Award (the “Notice”) and the attached Restricted Stock Unit Agreement (hereinafter “RSU Agreement”). For purposes of this RSU Agreement, terms shal

September 3, 2020 EX-99.2

Form of Inducement Stock Option Agreement

NOTICE OF STOCK OPTION GRANT Castlight Health, Inc. You have been granted an Option by Castlight Health, Inc. (the “Company”) to purchase shares of Common Stock of the Company subject to the terms and conditions of this Notice of Stock Option Grant (the “Notice”) and the Stock Option Agreement (the “Option Agreement”). Unless otherwise defined herein, any capitalized terms used herein will have th

September 3, 2020 S-8

- S-8

As filed with the Securities and Exchange Commission on September 3, 2020 Registration No.

August 4, 2020 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 4, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation or organization

July 31, 2020 EX-10.2

Separation Agreement, dated as of May 19, 2020, by and between the Registrant and Helen Kotchoubey

Exhibit 10.2 RCONFIDENTIAL SEPARATION AGREEMENT AND GENERAL RELEASE This Confidential Separation Agreement and General Release (“Agreement”) is made as of May 19, 2020, by and between Castlight Health, Inc., a Delaware Corporation (“Company”), and Helen Kotchoubey (“Employee”). The Agreement is based upon the following recitals of fact, which are hereby incorporated into this Agreement by referenc

July 31, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CAS

July 28, 2020 EX-99.1

Castlight Health Announces Second Quarter 2020 Results

Castlight Health Announces Second Quarter 2020 Results SAN FRANCISCO - July 28, 2020 - Castlight Health, Inc.

July 28, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 28, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission Fil

June 9, 2020 EX-99.1

June 9, 2020

Exhibit 99.1 June 9, 2020 Board of Directors Castlight Health, Inc. 50 Spear Street, Suite 400 San Francisco, CA 94105 Ladies & Gentlemen, Raging Capital Management, LLC is a significant shareholder of Castlight Health, Inc. (“Castlight” or the “Company”), currently owning over 9% of the outstanding shares. I am following up on the letter that I sent to you on April 21, 2020 expressing my serious

June 9, 2020 SC 13D/A

CSLT / Castlight Health, Inc. / Raging Capital Management, LLC - AMENDMENT NO. 1 TO SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 1)1 Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 (Title of Class of Securities) 14862Q 10 0 (CUSIP Number) STEVE WOLOSKY

June 3, 2020 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 3, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission File

May 21, 2020 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (a

May 8, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CA

May 7, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 3, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission File

May 7, 2020 EX-99.1

Castlight Health Announces First Quarter 2020 Results

Castlight Health Announces First Quarter 2020 Results SAN FRANCISCO - May 7, 2020 - Castlight Health, Inc.

May 7, 2020 EX-10.1

Third Amended and Restated Loan and Security Agreement, entered into as of May 5, 2020 by and among Silicon Valley Bank, Jiff, Inc. and Castlight Health, Inc.

THIRD AMENDED AND RESTATED LOAN AND SECURITY AGREEMENT THIS THIRD AMENDED AND RESTATED LOAN AND SECURITY AGREEMENT (this “Agreement”) dated as of May 4, 2020 (the “Effective Date”) by and among SILICON VALLEY BANK, a California corporation (“Bank”), JIFF INC.

May 4, 2020 8-K

Costs Associated with Exit or Disposal Activities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 4, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission File

April 28, 2020 8-K

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 22, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (State or othe

April 24, 2020 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 24, 2020 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 14, 2020 PRE 14A

CSLT / Castlight Health, Inc. PRE 14A - - PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: þ Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 31, 2020 EX-99.1

Castlight Health Receives NYSE Listing Compliance Notice

Castlight Health Receives NYSE Listing Compliance Notice SAN FRANCISCO, March 31, 2020 — Castlight Health, Inc.

March 31, 2020 8-K

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 30, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission Fi

March 30, 2020 EX-99.1

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13D (including amendments thereto) with respect to the Class B Common Stock, par value $0.0001 per share, of Castlight Health, Inc. This Joint Filing Agreement shall

March 30, 2020 EX-99.2

POWER OF ATTORNEY

Exhibit 99.2 POWER OF ATTORNEY Know all by these presents, that the undersigned hereby constitutes and appoints Frederick C. Wasch signing singly, the undersigned’s true and lawful attorney-in-fact to: 1. Execute for and on behalf of the undersigned all documents relating to the business of Raging Capital Management, LLC including, but not limited to, all filings with the Securities and Exchange C

March 30, 2020 SC 13D

CSLT / Castlight Health, Inc. / Raging Capital Management, LLC - SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. )1 Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 (Title of Class of Securities) 14862Q 10 0 (CUSIP Number) Steve Wolosky,

February 28, 2020 S-8

As filed with the Securities and Exchange Commission on February 28, 2020

As filed with the Securities and Exchange Commission on February 28, 2020 Registration No.

February 28, 2020 EX-10.20

Offer Letter, dated as of October 12, 2019, by and between the Registrant and Helen Kotchoubey.

October 12, 2019 Helen Kotchoubey Dear Helen, Congratulations! On behalf of Castlight Health, Inc.

February 28, 2020 EX-10.19

Offer Letter, dated as of November 18, 2019, by and between the Registrant and Will Bondurant.

EX-10.19 3 a201910-kex1019wbondur.htm EX-10.19 November 18, 2019 Will Bondurant Re: Promotion Dear Will, Thank you for your continued commitment and contributions to Castlight. I am pleased to inform you that you have been promoted to the position of Chief Financial Officer effective November 15, 2019 reporting to me. Your annual base salary will remain $300,000, less applicable withholdings. Your

February 28, 2020 EX-4.3

Description of Castlight Health, Inc. Common Stock Registered under Section 12 of the Securities Exchange Act of 1934.

Exhibit 4.3 Description of the Registrant’s Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934 The following description of capital stock of Castlight Health, Inc. (the “company,” “we,” “us” and “our”) summarizes certain provisions of our restated certificate of incorporation and our amended and restated bylaws. The description is intended as a summary, and is qual

February 28, 2020 10-K

Annual Report - 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the year ended December 31, 2019 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CASTLIGHT HEAL

February 28, 2020 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Subsidiaries of Castlight Health, Inc. Name of Subsidiary Jurisdiction Engage Technologies, Inc. Delaware Jiff, Inc. Delaware

February 25, 2020 EX-99.1

Castlight Health Announces Fourth Quarter and Full Year 2019 Results Company Provides Initial 2020 Financial Outlook

Castlight Health Announces Fourth Quarter and Full Year 2019 Results Company Provides Initial 2020 Financial Outlook SAN FRANCISCO - February 25, 2020 - Castlight Health, Inc.

February 25, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 25, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware 001-36330 26-1989091 (State or other jurisdiction of incorporation) (Commission

February 14, 2020 EX-99.1

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13G dated February 14, 2020 (including amendments thereto) with respect to the Class B Common Stock, par value $0.0001 per share, of Castlight Health, Inc. This Join

February 14, 2020 SC 13G/A

CSLT / Castlight Health, Inc. / MAVERICK CAPITAL LTD - AMENDMENT NO 7 Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No 7) CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule

February 14, 2020 SC 13G

CSLT / Castlight Health, Inc. / Raging Capital Management, LLC - SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(b) (Amendment No. )1 Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 (Title of Class of Securities) 14862Q 10 0 (CUSIP Number) D

February 13, 2020 SC 13G/A

CSLT / Castlight Health, Inc. / GAGNON NEIL - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

February 12, 2020 SC 13G/A

CSLT / Castlight Health, Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 5)* Name of issuer: Castlight Health Inc Title of Class of Securities: Common Stock CUSIP Number: 14862Q100 Date of Event Which Requires Filing of this Statement: December 31, 2019 Check the appropriate box to designate the rule pursuant to which this Schedule is filed:

February 6, 2020 SC 13G/A

CSLT / Castlight Health, Inc. / WELLCOME TRUST LTD (THE) as trustee of the WELLCOME TRUST - SC 13G/A Passive Investment

SC 13G/A CUSIP No. 14862Q100 13G Page 1 of 5 Pages SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (Amendment No. 2)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securitie

January 23, 2020 SC 13G/A

CSLT / Castlight Health, Inc. / OAK MANAGEMENT CORP - CASTLIGHT HEALTH, INC. Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 4)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rul

January 9, 2020 EX-99.1

Castlight Health Hires Keith Reynolds as New Chief Commercial Officer CVS Health and Aetna Veteran to Lead Castlight’s Sales and Customer Experience Functions Company Reiterates Full Year 2019 Guidance

Castlight Health Hires Keith Reynolds as New Chief Commercial Officer CVS Health and Aetna Veteran to Lead Castlight’s Sales and Customer Experience Functions Company Reiterates Full Year 2019 Guidance San Francisco – January 9, 2020 – Castlight Health, Inc.

January 9, 2020 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 January 8, 2020 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commiss

December 17, 2019 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 December 15, 2019 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commi

December 17, 2019 EX-10.1

Advisor Agreement, dated as of December 16, 2019, by and between the Company and Mr. Gupta.

Re: Castlight Health, Inc. – Advisory Services Dear Neeraj: I am pleased to formalize your role as an advisor (“Advisor”) to Castlight Health, Inc., a Delaware corporation (the “Company”), by this letter agreement (the “Agreement”). This Agreement will commence effective as of January 4, 2020 and shall continue until February 28, 2020 (the “Term”). As an Advisor, your role and responsibilities wil

October 31, 2019 EX-10.1

2014 Employee Stock Purchase Plan, as amended.

Castlight Health, Inc. 2014 Employee Stock Purchase Plan 1.Establishment of Plan. Castlight Health, Inc. proposes to grant options to purchase shares of Common Stock to eligible employees of the Company and its Participating Corporations pursuant to this Plan. The Company intends this Plan to qualify as an “employee stock purchase plan” under Code Section 423 (including any amendments to or replac

October 31, 2019 EX-10.2

Form of 2014 Employee Stock Purchase Plan enrollment/change form.

Castlight Health, Inc. (the “Company”) 2014 Employee Stock Purchase Plan (the “ESPP”) Capitalized terms used but not otherwise defined herein shall have the meanings given to them in the ESPP. Enrollment/Change Form (the “Agreement”) Section 1: Actions Check Desired Action: and Complete Sections: ☐ Enroll in the ESPP 2 + 3 + 4 + 20 ☐ Change Contribution Percentage 2 + 4 + 20 (for next offering per

October 31, 2019 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-3633

October 25, 2019 EX-10.2

Service Order Form 5 to Software as a Service (SaaS) Agreement, Enterprise Services, by and between Anthem, Inc. and Castlight Health, Inc., dated October 19, 2019.

CERTAIN CONFIDENTIAL INFORMATION CONTAINED IN THIS DOCUMENT, MARKED BY [***], HAS BEEN OMITTED BECAUSE IT IS NOT MATERIAL AND WOULD LIKELY CAUSE COMPETITIVE HARM TO THE COMPANY IF PUBLICLY DISCLOSED.

October 25, 2019 EX-99.1

Castlight Health Announces Third Quarter 2019 Results Signs Anthem, Inc. to Enterprise License Agreement Launches Personalized High-Touch Offering for Health Navigation Platform Customers Expands Leadership Team

Castlight Health Announces Third Quarter 2019 Results Signs Anthem, Inc. to Enterprise License Agreement Launches Personalized High-Touch Offering for Health Navigation Platform Customers Expands Leadership Team SAN FRANCISCO - October 24, 2019 - Castlight Health, Inc. (NYSE:CSLT), a leading health benefits platform provider, today announced results for its third quarter ended September 30, 2019.

October 25, 2019 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 October 19, 2019 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commis

October 25, 2019 EX-10.1

Software as a Service (SaaS) Agreement, by and between Anthem, Inc. and Castlight Health, Inc. as of November 1, 2015, as amended on October 19, 2019.

CERTAIN CONFIDENTIAL INFORMATION CONTAINED IN THIS DOCUMENT, MARKED BY [***], HAS BEEN OMITTED BECAUSE IT IS NOT MATERIAL AND WOULD LIKELY CAUSE COMPETITIVE HARM TO THE COMPANY IF PUBLICLY DISCLOSED.

July 31, 2019 EX-10.1

Offer Letter, dated as of July 26, 2019, by and between the Registrant and Maeve O’Meara.

July 26, 2019 Maeve O’Meara Re: Promotion Dear Maeve, Thank you for your continued commitment and contributions to Castlight.

July 31, 2019 10-Q

Quarterly Report - 10-Q Q2'19

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330

July 31, 2019 EX-10.2

Offer Letter, dated as of July 26, 2019, by and between the Registrant and Siobhan Nolan Mangini.

July 26, 2019 Siobhan Nolan Mangini Re: Promotion Dear Siobhan, Thank you for your continued commitment and contributions to Castlight.

July 30, 2019 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 26, 2019 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commissio

July 30, 2019 EX-99.2

Castlight Health Announces Key Management Changes Maeve O’Meara Named Chief Executive Officer; Siobhan Nolan Mangini Named President

Castlight Health Announces Key Management Changes Maeve O’Meara Named Chief Executive Officer; Siobhan Nolan Mangini Named President SAN FRANCISCO (July 30, 2019) – Castlight Health, Inc.

July 30, 2019 EX-99.1

Castlight Health Announces Second Quarter 2019 Results Updates Full Year 2019 Guidance & Announces Management Changes

Castlight Health Announces Second Quarter 2019 Results Updates Full Year 2019 Guidance & Announces Management Changes SAN FRANCISCO - July 30, 2019 - Castlight Health, Inc.

June 5, 2019 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 5, 2019 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commission

May 3, 2019 10-Q

CSLT / Castlight Health, Inc. 10-Q Quarterly Report 10-Q Q1'19

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2019 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-3633

May 2, 2019 EX-99.1

Castlight Health Announces First Quarter 2019 Results

Castlight Health Announces First Quarter 2019 Results SAN FRANCISCO - May 2, 2019 - Castlight Health, Inc.

May 2, 2019 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 2, 2019 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commission

April 26, 2019 DEFA14A

CSLT / Castlight Health, Inc. DEFA14A DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 26, 2019 DEF 14A

CSLT / Castlight Health, Inc. DEF 14A DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 1, 2019 S-8

CSLT / Castlight Health, Inc. S-8 2019

As filed with the Securities and Exchange Commission on March 1, 2019 Registration No.

March 1, 2019 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Subsidiaries of Castlight Health, Inc. Name of Subsidiary Jurisdiction Engage Technologies, Inc. Delaware Jiff, Inc. Delaware

March 1, 2019 EX-10.16

Job Offer Letter, dated as of July 26, 2017, by and between the Registrant and Eric Chan.

[Castlight Logo Here] July 26, 2017 Eric Chan [address line 1 intentionally omitted] [address line 2 intentionally omitted] Dear Eric Chan, Congratulations! On behalf of Castlight Health, Inc.

March 1, 2019 EX-10.17

Promotion Letter, dated as of May 31, 2018, by and between the Registrant and Maeve O’Meara.

May 31, 2018 Maeve O’Meara Dear Maeve, Thank you for your continued commitment and contributions to Castlight.

March 1, 2019 EX-10.18

Promotion Letter, effective September 17, 2018, by and between the Registrant and Neeraj Gupta.

Neeraj Gupta Re: Promotion to EVP, Engineering Dear Neeraj, Thank you for your continued commitment and contributions to Castlight.

March 1, 2019 10-K

CSLT / Castlight Health, Inc. 2018 10-K (Annual Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K [x] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the year ended December 31, 2018 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CASTLIGHT

February 28, 2019 EX-99.1

Castlight Health Announces Fourth Quarter and Full Year 2018 Results Full Year 2018 Total Revenue of $156.4 million, Up 18% Year-over-Year Generated $7.5 Million in Cash Flow from Operations in the Fourth Quarter

Castlight Health Announces Fourth Quarter and Full Year 2018 Results Full Year 2018 Total Revenue of $156.

February 28, 2019 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 28, 2019 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commi

February 14, 2019 EX-24.A

Power of Attorney

Exhibit 24.A Power of Attorney KNOW ALL MEN BY THESE PRESENTS, that I, Lee S. Ainslie III, hereby make, constitute and appoint Mark Gurevich as my agent and attorney-in-fact for the purpose of executing (i) in my personal capacity or (ii) in my capacity as manager or other officer or representative of Maverick Capital Management, LLC, Maverick Capital, Ltd. or any affiliate of either, all document

February 14, 2019 EX-24.B

Power of Attorney

Exhibit 24.B Power of Attorney KNOW ALL MEN BY THESE PRESENTS, that I, Andrew H. Warford, hereby make, constitute and appoint Mark Gurevich as my agent and attorney-in-fact for the purpose of executing (i) in my personal capacity or (ii) in my capacity as manager or other officer or representative of Maverick Capital, Ltd. or any affiliate of either, all documents to be filed with or delivered to

February 14, 2019 EX-99.A

Joint Filing Agreement

Exhibit 99.A Joint Filing Agreement The undersigned hereby agree that the statement on Schedule 13G/A with respect to the Class B Common Stock, $0.0001 par value per share of Castlight Health, Inc., dated as of February 14, 2019, is, and any amendments thereto (including amendments on Schedule 13D) signed by each of the undersigned shall be, filed on behalf of each of us pursuant to and in accorda

February 14, 2019 SC 13G

CSLT / Castlight Health, Inc. / GAGNON NEIL - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) February 8, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designa

February 14, 2019 SC 13G/A

CSLT / Castlight Health, Inc. / MAVERICK CAPITAL LTD - AMENDMENT NO 6 Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No 6) CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule

February 11, 2019 SC 13G/A

CSLT / Castlight Health, Inc. / VANGUARD GROUP INC Passive Investment

castlighthealthinc.htm - Generated by SEC Publisher for SEC Filing SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 4 )* Name of issuer: Castlight Health Inc Title of Class of Securities: Common Stock CUSIP Number: 14862Q100 Date of Event Which Requires Filing of this Statement: December 31, 2018 Check the appropriate

February 6, 2019 SC 13G/A

CSLT / Castlight Health, Inc. / WELLCOME TRUST LTD (THE) as trustee of the WELLCOME TRUST - SC 13G/A Passive Investment

SC 13G/A CUSIP No. 14862Q100 13G Page 1 of 5 Pages SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (Amendment No. 1)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities)

January 28, 2019 SC 13G/A

CSLT / Castlight Health, Inc. / OAK MANAGEMENT CORP Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 3)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rul

January 18, 2019 SC 13G/A

CSLT / Castlight Health, Inc. / GAGNON NEIL - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

November 7, 2018 10-Q

CSLT / Castlight Health, Inc. 10-Q Q3'18 (Quarterly Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2018 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-

November 6, 2018 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 6, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commis

November 6, 2018 EX-99.1

Castlight Health Announces Third Quarter 2018 Results Total Revenue of $40.0 million, Up 16% Year-over-Year

Castlight Health Announces Third Quarter 2018 Results Total Revenue of $40.0 million, Up 16% Year-over-Year SAN FRANCISCO - November 6, 2018 - Castlight Health, Inc. (NYSE:CSLT), a leading health benefits platform provider, today announced results for its third quarter ended September 30, 2018. “Our team executed exceptionally well this quarter, which resulted in the successful launch of our Compl

September 20, 2018 SC 13G

CSLT / Castlight Health, Inc. / GAGNON NEIL - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) September 10, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to desig

August 16, 2018 8-K/A

Costs Associated with Exit or Disposal Activities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A Amendment No. 1 Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 15, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization)

August 1, 2018 EX-10.17

Amendment to Offer Letter between the Registrant and Robert Derek Newell, dated June 11, 2018

JUNE 11, 2018 Robert Derek Newell [Personal address] Re: Amendment to Offer Letter Dear Derek, This letter (this “Amendment”) serves to amend the Offer Letter between you and Castlight Health, Inc.

August 1, 2018 10-Q

CSLT / Castlight Health, Inc. CSLT Q2'18 10-Q (Quarterly Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2018 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330

July 30, 2018 EX-99.1

Castlight Health Announces Second Quarter 2018 Results Total Revenue of $37.8 million, Up 16% Year-over-Year

Castlight Health Announces Second Quarter 2018 Results Total Revenue of $37.8 million, Up 16% Year-over-Year SAN FRANCISCO - July 30, 2018 - Castlight Health, Inc. (NYSE:CSLT), a leading health benefits platform provider, today announced results for its second quarter ended June 30, 2018. “We’ve seen strong validation over the last two quarters that our health navigation solution is penetrating th

July 30, 2018 8-K

Financial Statements and Exhibits, Costs Associated with Exit or Disposal Activities, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 30, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commissio

June 20, 2018 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 20, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commissio

June 11, 2018 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 8, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commission

June 11, 2018 EX-99.1

Castlight Health Announces Management & Board of Directors Changes

Castlight Health Announces Management & Board of Directors Changes SAN FRANCISCO – June 11, 2018 – Castlight Health, Inc.

May 10, 2018 10-Q

CSLT / Castlight Health, Inc. 10-Q (Quarterly Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2018 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-3633

May 10, 2018 EX-99.1

Castlight Health Announces First Quarter 2018 Results Total Revenue of $36.5 million, Up 32% Year-over-Year

Castlight Health Announces First Quarter 2018 Results Total Revenue of $36.5 million, Up 32% Year-over-Year SAN FRANCISCO - May 10, 2018 - Castlight Health, Inc. (NYSE:CSLT), a leading health benefits platform provider, today announced results for its first quarter ended March 31, 2018. “We launched a record number of new customers in the first quarter, including more than twenty on Engage, our fi

May 10, 2018 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 10, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commission

April 27, 2018 DEFA14A

CSLT / Castlight Health, Inc. DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 27, 2018 DEF 14A

CSLT / Castlight Health, Inc. DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 1, 2018 S-8

CSLT / Castlight Health, Inc. S-8

As filed with the Securities and Exchange Commission on March 1, 2018 Registration No.

March 1, 2018 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Subsidiaries of Castlight Health, Inc. Name of Subsidiary Jurisdiction Engage Technologies, Inc. Delaware Jiff, Inc. Delaware

March 1, 2018 10-K

CSLT / Castlight Health, Inc. 10-K (Annual Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K [x] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the year ended December 31, 2017 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CASTLIGHT

February 21, 2018 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 21, 2018 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-363

February 21, 2018 EX-99.1

Castlight Health Announces Fourth Quarter and Full Year 2017 Results Full Year 2017 Total Revenue of $131.4 million, Up 29% Year-over-Year

Exhibit Castlight Health Announces Fourth Quarter and Full Year 2017 Results Full Year 2017 Total Revenue of $131.

February 13, 2018 SC 13G/A

CSLT / Castlight Health, Inc. / GAGNON NEIL - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2017 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

February 12, 2018 SC 13G/A

CSLT / Castlight Health, Inc. / Colella Giovanni M. - NONE Passive Investment

Schedule 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 03)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2017 (Date of Event Which Requires Filing of this Statement) Check the appropriat

February 12, 2018 SC 13G/A

CSLT / Castlight Health, Inc. / MAVERICK CAPITAL LTD - AMENDMENT NO 5 Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No 5) CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2017 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule

February 12, 2018 EX-99.A

Joint Filing Agreement

Exhibit A Joint Filing Agreement The undersigned hereby agree that the statement on Schedule 13G/A with respect to the Class B Common Stock, $0.

February 8, 2018 SC 13G/A

CSLT / Castlight Health, Inc. / VANGUARD GROUP INC Passive Investment

castlighthealthinc.htm - Generated by SEC Publisher for SEC Filing SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 3 )* Name of issuer: Castlight Health Inc Title of Class of Securities: Common Stock CUSIP Number: 14862Q100 Date of Event Which Requires Filing of this Statement: December 31, 2017 Check the appropriate

January 26, 2018 EX-99.2

TRADING DATA

EXHIBIT 99.2 TRADING DATA Date Aggregate Shares Sold Price Per Share (USD)(1) Where and How Transaction Effected November 6, 2017 16,507 $ 4.0662 (2) Open Market Sale November 7, 2017 17,300 $ 4.0207 (3) Open Market Sale November 10, 2017 3,000 $ 4.0000 Open Market Sale November 22, 2017 2,350 $ 4.0000 Open Market Sale November 24, 2017 207 $ 4.0000 Open Market Sale November 29, 2017 33,733 $ 3.90

January 26, 2018 EX-99.1

JOINT FILING AGREEMENT

EXHIBIT 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1) under the Securities Exchange Act of 1934, as amended, each of the undersigned hereby agrees to the joint filing, along with the other such undersigned, of a statement on Schedule 13D (including amendments thereto) with respect to the Class B common stock, par value $0.0001 per share, of Castlight Health, Inc., and that this a

January 26, 2018 SC 13D/A

CSLT / Castlight Health, Inc. / SAP SE - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Castlight Health, Inc. (Name of Issuer) Class B Common Stock, par value $0.0001 per share (Title of Class of Securities) 14862Q100 (CUSIP Number) Wendy Boufford Assistant General Counsel c/o SAP Labs 3410 Hillview Avenue Palo Alto, California 94304 +1 65

January 3, 2018 EX-24

POWER OF ATTORNEY

POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the undersigned hereby constitutes and appoints Jennifer Chaloemtiarana and Trevor Dutcher, and each of them, as his true and lawful attorney-in-fact to: (1) execute for and on behalf of the undersigned, in the undersigned's capacity as a representative of Castlight Health, Inc.

October 27, 2017 EX-99.1

Jiff, Inc. 2010 Stock Plan and form of option agreement

Exhibit JIFF INC. 2010 STOCK PLAN 1. Purposes of the Plan . The purposes of this 2010 Stock Plan are to attract and retain the best available personnel for positions of substantial responsibility, to provide additional incentive to Employees and Consultants, and to promote the success of the Company?s business. Options granted under the Plan may be Incentive Stock Options or Nonstatutory Stock Opt

October 27, 2017 S-8

Castlight Health S-8

Document As filed with the Securities and Exchange Commission on October 27, 2017 Registration No.

October 27, 2017 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2017

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2017 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-

October 25, 2017 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 October 21, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-3633

October 25, 2017 EX-99.1

Castlight Health Announces Third Quarter 2017 Results Total Revenue of $34.6 million, Up 36% Year-over-Year

Exhibit Castlight Health Announces Third Quarter 2017 Results Total Revenue of $34.

September 22, 2017 EX-24

POWER OF ATTORNEY

POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the undersigned hereby constitutes and appoints Jennifer Chaloemtiarana and Trevor Dutcher, and each of them, as his true and lawful attorney-in-fact to: (1) execute for and on behalf of the undersigned, in the undersigned's capacity as a representative of Castlight Health, Inc.

September 22, 2017 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 22, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36

August 4, 2017 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2017

Document Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

August 2, 2017 EX-99.1

Castlight Health Announces Second Quarter 2017 Results Total Revenue of $32.1 million, Up 36% Year-over-Year Company Reiterates 2017 Guidance

Exhibit Castlight Health Announces Second Quarter 2017 Results Total Revenue of $32.

August 2, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 2, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330

June 26, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 22, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (

May 19, 2017 EX-99.1

INDEPENDENT AUDITORS’ REPORT

Exhibit INDEPENDENT AUDITORS? REPORT Board of Directors Jiff, Inc. Mountain View, California Report on the Financial Statements We have audited the accompanying financial statements of Jiff, Inc. (a Delaware corporation), which comprise the balance sheets as of December 31, 2016 and 2015, and the related statements of operations, stockholders? equity, and cash flows for the years then ended, and t

May 19, 2017 8-K/A

Castlight Health 8-K/A (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 3, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330

May 19, 2017 EX-99.2

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

Exhibit UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION The following sets forth certain unaudited pro forma condensed combined financial information giving effect to the acquisition of Jiff, Inc.

May 19, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 15, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (C

May 10, 2017 SC 13G/A

CSLT / Castlight Health, Inc. / MAVERICK CAPITAL LTD - AMENDMENT NO. 4 Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 4) CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) April 3, 2017 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pur

May 10, 2017 EX-99.A

Joint Filing Agreement

Exhibit A Joint Filing Agreement The undersigned hereby agree that the statement on Schedule 13G/A with respect to the Class B Common Stock, $0.

April 28, 2017 DEFA14A

Castlight Health DEFA14A

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permit

April 28, 2017 DEF 14A

Castlight Health DEF 14A

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permit

April 28, 2017 EX-2.3

AMENDMENT NO. 1 TO WARRANT

Exhibit 2.3 AMENDMENT NO. 1 TO WARRANT This Amendment No. 1 to Warrant (this “Amendment”) is made and entered into as of April 24, 2017 (the “Amendment Date”), by and among SAP Technologies, Inc., a Delaware corporation (the “Holder”), and Castlight Health, Inc., a Delaware corporation (the “Company”). RECITALS WHEREAS, the Company and the Holder are parties to that certain Warrant dated May 17, 2

April 28, 2017 EX-10.17

Job Offer Letter, dated as of January 4, 2017, by and between the Registrant and Derek Newell.

Exhibit C ASTLIGHT H EALTH , I NC . January 3, 2017 Derek Newell 96 Hiller Drive Oakland, California 94618 Dear Derek: Castlight Health, Inc. (the ? Company ?) is pleased to offer you employment on the terms set forth below. This employment offer is contingent on the closing (the ? Closing ?) of the Company?s acquisition of Jiff, Inc. (? Target ? and such acquisition, the ? Transaction ?) pursuant

April 28, 2017 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2017

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2017 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-3633

April 28, 2017 SC 13D/A

CSLT / Castlight Health, Inc. / SAP SE - SCHEDULE 13D AMENDMENT Activist Investment

Schedule 13D Amendment UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 26, 2017 EX-99.2

AMENDMENT NO. 1 TO WARRANT

Exhibit AMENDMENT NO. 1 TO WARRANT This Amendment No. 1 to Warrant (this ? Amendment ?) is made and entered into as of April 24, 2017 (the ? Amendment Date ?), by and among SAP Technologies, Inc., a Delaware corporation (the ? Holder ?), and Castlight Health, Inc., a Delaware corporation (the ? Company ?). RECITALS WHEREAS, the Company and the Holder are parties to that certain Warrant dated May 1

April 26, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 24, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330

April 26, 2017 EX-99.1

Castlight Health Announces First Quarter 2017 Results Total Revenue of $27.7 Million, Up 22% Y-o-Y GAAP & Non-GAAP Gross Margin Increased by 1,100 Basis Points Y-o-Y GAAP & Non-GAAP Operating Loss Reduced by $6 Million and $7 Million Y-o-Y, Respectiv

Exhibit Castlight Health Announces First Quarter 2017 Results Total Revenue of $27.

April 12, 2017 SC 13D/A

CSLT / Castlight Health, Inc. / Venrock Associates VI, L.P. - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* CASTLIGHT HEALTH, INC. (Name of Issuer) CLASS B COMMON STOCK (Title of Class of Securities) 14862Q100 (CUSIP Number) Attention: General Counsel Venrock 3340 Hillview Avenue Palo Alto, California 94304 Name, Address and Telephone Number of Person Author

April 5, 2017 EX-24

POWER OF ATTORNEY

POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the undersigned hereby constitutes and appoints Jennifer Chaloemtiarana and Trevor Dutcher, and each of them, as his true and lawful attorney-in-fact to: (1) execute for and on behalf of the undersigned, in the undersigned's capacity as a representative of Castlight Health, Inc.

April 5, 2017 EX-24

POWER OF ATTORNEY

POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the undersigned hereby constitutes and appoints Jennifer Chaloemtiarana and Trevor Dutcher, and each of them, as his true and lawful attorney-in-fact to: (1) execute for and on behalf of the undersigned, in the undersigned's capacity as a representative of Castlight Health, Inc.

April 3, 2017 EX-99.1

Castlight Health Completes Strategic Acquisition of Jiff

Exhibit Castlight Health Completes Strategic Acquisition of Jiff San Francisco, CA ? April 3, 2017 ? Castlight Health, Inc.

April 3, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 3, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (

April 3, 2017 EX-10.1

Second Amended and Restated Loan and Security Agreement, as of April 3, 2017, by and among Silicon Valley Bank, Jiff Inc., and Castlight Health, Inc.

Exhibit SECOND AMENDED AND RESTATED LOAN AND SECURITY AGREEMENT THIS SECOND AMENDED AND RESTATED LOAN AND SECURITY AGREEMENT (this ? Agreement ?) dated as of April 3, 2017 (the ? Effective Date ?) by and among SILICON VALLEY BANK, a California corporation (? Bank ?), JIFF INC.

March 21, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 17, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330

March 9, 2017 8-K

Castlight Health 8-K (Current Report/Significant Event)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 9, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (

March 9, 2017 425

Castlight Health 8-K (Prospectus)

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 9, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (

March 7, 2017 425

Castlight Health 425 (Prospectus)

3.7.17 425 Filing Combined Document Filed by Castlight Health, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Jiff, Inc. Registration Statement No: 333-215861 The following is an investor presentation given by Castlight Health, Inc. on March 7, 2017: Investor Ove

March 1, 2017 S-8

Castlight Health S-8

Document As filed with the Securities and Exchange Commission on March 1, 2017 Registration No.

March 1, 2017 EX-10.12

Job Offer Letter, dated as of October 7, 2014, by and between the Registrant and John McCracken

[CASTLIGHT] JOB OFFER LETTER October 27, 2014 John McCracken Dear John: On behalf of Castlight Health, Inc.

March 1, 2017 EX-21.1

Subsidiaries of Castlight Health, Inc. Name of Subsidiary Jurisdiction Castlight, Inc. Delaware Neptune Acquisition Subsidiary, Inc. Delaware

Exhibit 21.1 Subsidiaries of Castlight Health, Inc. Name of Subsidiary Jurisdiction Castlight, Inc. Delaware Neptune Acquisition Subsidiary, Inc. Delaware

March 1, 2017 EX-99.1

Certain Excerpts from the Prospectus dated February 22, 2017 filed on February 22, 2017 pursuant to Rule424(b)(3) relating to the Registration Statement on Form S-4, as amended (No. 333- 215861) of the Registrant.

Risks related to the Merger The exchange ratio is not adjustable based on the market price of Castlight Class B common stock, so the merger consideration at the time of the completion of the merger may have a greater or lesser value than at the time the merger agreement was signed.

March 1, 2017 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K [x] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the year ended December 31, 2016 [ ] TRANSITION REPORT PURSUANT TO SECTION

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K [x] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the year ended December 31, 2016 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36330 CASTLIGHT

February 28, 2017 EX-99.1

February Org Changes Email

Exhibit Exhibit 99.1 February Org Changes Email John D email to Jiff & Castlight Team? We?re making excellent progress on our Road to One . We have an incredible opportunity to take a big step forward together on our mission to make health care work better for our customers and users. The first step is integrating Jiff and Castlight successfully, so it is great to be off to such a strong start. Wh

February 28, 2017 425

Castlight Health 425 (Prospectus)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 28, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36330 (Commi

February 28, 2017 EX-99.2

February Org Changes Emails

Exhibit Exhibit 99.2 February Org Changes Emails Derek email to Jiff & Castlight Team? As John Doyle just mentioned, I?m excited to announce my move-forward leadership team. All of these are proven leaders who have the experience and knowledge needed to build upon the current foundation and drive us to our next level of success. John and I are very confident in the entire leadership team and are t

February 28, 2017 EX-99.2

February Org Changes Emails

Exhibit Exhibit 99.2 February Org Changes Emails Derek email to Jiff & Castlight Team? As John Doyle just mentioned, I?m excited to announce my move-forward leadership team. All of these are proven leaders who have the experience and knowledge needed to build upon the current foundation and drive us to our next level of success. John and I are very confident in the entire leadership team and are t

February 28, 2017 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 28, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-363

February 28, 2017 EX-99.1

February Org Changes Email

Exhibit Exhibit 99.1 February Org Changes Email John D email to Jiff & Castlight Team? We?re making excellent progress on our Road to One . We have an incredible opportunity to take a big step forward together on our mission to make health care work better for our customers and users. The first step is integrating Jiff and Castlight successfully, so it is great to be off to such a strong start. Wh

February 24, 2017 425

Castlight Health 425 (Prospectus)

Document Filed by Castlight Health, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Jiff, Inc. Registration Statement No: 333-215861 On February, 24, 2017, the following questions and answers summary was distributed by Jiff, Inc. to employees of Jiff, Inc.: Questi

February 23, 2017 425

Castlight Health 425 (Prospectus)

Document Filed by Castlight Health, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Jiff, Inc. Commission File No: 001-36330 The following is a blog post dated February 23, 2017 by Derek Newell, Chief Executive Officer of Jiff, Inc.: A New Chapter for Jiff When I

February 22, 2017 424B3

TO THE STOCKHOLDERS OF CASTLIGHT HEALTH, INC. AND JIFF, INC. — MERGER PROPOSAL — YOUR VOTE IS VERY IMPORTANT

Document Filed Pursuant to Rule 424(b)(3) Registration No. 333-215861 TO THE STOCKHOLDERS OF CASTLIGHT HEALTH, INC. AND JIFF, INC. ? MERGER PROPOSAL ? YOUR VOTE IS VERY IMPORTANT February 22, 2017 To the stockholders of Castlight Health, Inc. and Jiff, Inc., On January 4, 2017, the boards of each of Castlight Health, Inc. (?Castlight?) and Jiff, Inc. (?Jiff?) have approved the merger of a wholly o

February 16, 2017 425

Castlight Health 425 (Prospectus)

Document Filed by Castlight Health, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Jiff, Inc. Commission File No: 001-36330 On February 15, 2017, Castlight Health, Inc. (? Castlight ?) hosted a conference call to discuss its fourth quarter and full year 2016 resu

February 15, 2017 425

Castlight Health 425 (Prospectus)

Exhibit Filed by Castlight Health, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Jiff, Inc. Commission File No: 001-36330 The following is a press release issued by Castlight Health, Inc. on February 15, 2017. Castlight Health Announces Fourth Quarter and Full Y

February 15, 2017 EX-99.1

Castlight Health Announces Fourth Quarter and Full Year 2016 Results Total Revenue of $101.7 Million for the Year, Up 35% Y-o-Y Record High Gross Margin and $1.7M Cash Used in Operations in 4Q 2016 Jiff Acquisition Expected to Close at the End of 1Q

Exhibit Castlight Health Announces Fourth Quarter and Full Year 2016 Results Total Revenue of $101.

February 15, 2017 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

Document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 15, 2017 Date of Report (Date of earliest event reported) CASTLIGHT HEALTH, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-363

February 14, 2017 SC 13G/A

Castlight Health AMENDMENT NO 2 (Passive Acquisition of More Than 5% of Shares)

SC 13G/A 1 ss3071113ga.htm AMENDMENT NO 2 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No 2) CASTLIGHT HEALTH, INC. (Name of Issuer) Class B Common Stock, $0.0001 par value per share (Title of Class of Securities) 14862Q100 (CUSIP Number) December 31, 2016 (Date of Event Which Requires Filing of this Statement) Check

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