Sec Form 4 Filing - Kosloske Michael W @ Health Insurance Innovations, Inc. - 2019-06-04

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

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

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1. Name and Address of Reporting Person Kosloske Michael W 2. Issuer Name and Ticker or Trading Symbol Health Insurance Innovations, Inc. [ HIIQ] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 16221 VILLARREAL DE AVILA, 3. Date of Earliest Transaction (MM/DD/YY) 06/04/2019 (Street) TAMPA, FL33613 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) _____ Form filed by One Reporting Person __ X __ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Class A Common Stock 06/04/2019 M( 1 ) 40,834 A $ 23.8 105,136 D Class A Common Stock 06/04/2019 D 33,816 ( 2 ) D $ 28.74 71,320 D Class B Common Stock ( 3 ) 2,416,667 I See Footnote ( 4 ) Class A Common Stock 125,000 I See Footnote ( 5 ) Class A Common Stock 5,643 ( 6 ) I See Footnote ( 6 )

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Stock Appreciation Rights $ 23.8 06/04/2019 M( 1 ) 40,834 ( 7 ) 06/07/2019 Class A Common Stock 40,834 $ 0 0 D Membership Interests in Health Plan Intermediaries Holdings, ( 3 ) $ 0 ( 3 ) ( 3 ) Class A Common Stock 0 2,416,667 I See Footnote ( 8 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Kosloske Michael W 16221 VILLARREAL DE AVILA TAMPA, FL33613 X Health Plan Intermediaires, LLC C/O HEALTH INSURANCE INNOVATIONS, INC. 15438 N. FLORIDA AVENUE, SUITE 201 TAMPA, FL33613 X Health Plan Intermediaries Sub, LLC C/O HEALTH INSURANCE INNOVATIONS, INC. 15438 N. FLORIDA AVENUE, SUITE 201 TAMPA, FL33613 X Signatures /s/ Michael W. Kosloske 06/06/2019 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Represents the exercise of stock appreciation rights prior to the expiration thereof. ( 2 )Shares retained by the issuer to satisfy the exercise price of stock appreciation rights exercised by the Reporting Person. ( 3 )Each share of Class B Common Stock held by the reporting persons, together with one Series B Membership Interest held by the reporting persons in Health Plan Intermediaries Holdings, LLC ("HPIH"), are together exchangeable, at any time, at the reporting persons' election, for one share of Class A Common Stock. This exchange right has no expiration date. ( 4 )This number of shares consists of 2,391,701 shares of Class B Common Stock held of record by Health Plan Intermediaries, LLC ("HPI") and 24,966 shares of Class B Common Stock held by Health Plan Intermediaries Sub, LLC ("HPIS"). Michael Kosloske is the sole member and primary manager of HPI, and has sole voting and dispositive power over the shares held by HPI. HPI is the sole managing member of HPIS and has sole voting and dispositive power over the shares held by HPIS. Mr. Kosloske, by virtue of his control of HPI and HPI's control of HPIS, may be deemed to beneficially own all the shares of Class B Common Stock held of record by each of HPI and HPIS. ( 5 )This number of shares consists of 123,750 shares of Class A Common Stock held of record by HPI and 1,250 shares of Class A Common Stock held by HPIS. Michael Kosloske is the sole member and primary manager of HPI, and has sole voting and dispositive power over the shares held by HPI. HPI is the sole managing member of HPIS and has sole voting and dispositive power over the shares held by HPIS. Mr. Kosloske, by virtue of his control of HPI and HPI's control of HPIS, may be deemed to beneficially own all the shares of Class A Common Stock held of record by each of HPI and HPIS. ( 6 )By Lori Kosloske. Michael Kosloske and Lori Kosloske are husband and wife. ( 7 )These stock-settled stock appreciation rights were granted to the Reporting Person under the Issuer's Long-Term Incentive Plan and, in accordance with the terms of the Long-Term Incentive Plan and an award agreement under the Long-Term Incentive Plan, vested in January 2018 upon the termination of the Reporting Person's employment with the Company. ( 8 )This number consists of 2,391,701 Class B Membership Interests in HPIH held of record by HPI and 24,966 interests held by HPIS. Michael Kosloske is the sole member and primary manager of HPI, and has sole voting and dispositive power over the interests held by HPI. HPI is the sole managing member of HPIS and has sole voting and dispositive power over the interests held by HPIS. Mr. Kosloske, by virtue of his control of HPI and HPI's control of HPIS, may be deemed to beneficially own all the Class B Membership Interests of HPIH held of record by each of HPI and HPIS.

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