Ownership Submission
FORM 4
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES

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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(Print or Type Responses)
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)
__X__ Director __X__ 10% Owner
_____ Officer (give title below) _____ Other (specify below)
(Last)
(First)
(Middle)
15438 N. FLORIDA AVENUE, SUITE 201
3. Date of Earliest Transaction (Month/Day/Year)
09/10/2018
(Street)

TAMPA, FL 33613
4. If Amendment, Date Original Filed(Month/Day/Year)
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 (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 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 09/10/2018   G   18,100 (1) D $ 0 7,979 D  
Class A Common Stock 09/10/2018   G   7,979 (1) D $ 0 0 D  
Class A Common Stock 04/22/2019   M(2)   106,173 A $ 9.2 106,173 D  
Class A Common Stock 04/22/2019   D   41,871 (3) D $ 24.85 64,302 D  
Class B Common Stock (4)               2,416,667 I See Footnote (5)
Class A Common Stock               125,000 I See Footnote (6)
Class A Common Stock               5,643 (7) I See Footnote (7)

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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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 (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 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
(Month/Day/Year)
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 $ 9.8 04/22/2019   M(2)     106,173   (8) 06/07/2019 Common Stock 106,173 $ 0 0 D  
Stock Appreciation Rights $ 23.8               (8) 06/07/2019 Common Stock 40,834   40,834 D  
Membership Int in Health Plan Intermediaries Holdings, LLC (4) $ 0               (4)   (4) Class A Common Stock 125,000   2,416,667 I See Footnote (9)

Reporting Owners

Reporting Owner Name / Address Relationships
 Director  10% Owner  Officer  Other
Kosloske Michael W
15438 N. FLORIDA AVENUE
SUITE 201
TAMPA, FL 33613
  X   X    
Health Plan Intermediaires, LLC
C/O HEALTH INSURANCE INNOVATIONS, INC.
15438 N. FLORIDA AVENUE, SUITE 201
TAMPA, FL 33613
    X    
Health Plan Intermediaries Sub, LLC
C/O HEALTH INSURANCE INNOVATIONS, INC.
15438 N. FLORIDA AVENUE, SUITE 201
TAMPA, FL 33613
    X    

Signatures

 /s/ Michael W. Kosloske   04/24/2019
**Signature of Reporting Person Date

Explanation of Responses:

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1) Represents shares previously reported as being held by the Michael W. Kosloske 2012 Descendant's Trust as to which the Reporting Person exercised a power of substitution and subsequently gifted.
(2) Represents the exercise of stock appreciation rights prior to the expiration thereof.
(3) Shares retained by the issuer to satisfy the exercise price of stock appreciation rights exercised by the Reporting Person.
(4) 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.
(5) 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.
(6) 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.
(7) By Lori Kosloske. Michael Kosloske and Lori Kosloske are husband and wife. Share number previously incorrectly reported as 7,203.
(8) These stock-settled stock appreciation rights were granted to the Reporting Person under the Issuer's Long-Term Incentive Plan and vest 25% on each of the first and second anniversaries of grant date and 50% on the third anniversary, subject to the terms of the Long-Term Incentive Plan and an award agreement under the Long-Term Incentive Plan.
(9) 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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