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

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

1. Name and Address of Reporting Person *

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
__ X __ Officer (give title below)      _____ Other (specify below)
Chairman, President and CEO
(Last)          (First)          (Middle)

15438 N. FLORIDA AVENUE, SUITE 201
3. Date of Earliest Transaction (MM/DD/YYYY)

5/21/2014
(Street)

TAMPA, FL 33613
(City)        (State)        (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)

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

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

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Class A Common Stock   5/21/2014     S    2800   (1) D $10.3948   (2) 38615   D    
Class A Common Stock   5/22/2014     S    1900   (1) D $10.3918   (3) 36715   D    
Class A Common Stock                  8900   I   See Footnote   (4)
Class A Common Stock                  8566667   (5) I   See Footnote   (5)

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares

Explanation of Responses:
( 1)  The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan, which was adopted by Mr. Kosloske on December 13, 2013.
( 2)  The price reported in Column 4 represents the weighted average price of multiple transactions with a range of prices between $10.25 to $10.51 inclusive. Mr. Kosloske undertakes to provide, upon request by the SEC, Health Insurance Innovations, Inc., or a security holder of Health Insurance Innovations, Inc., full information regarding the number of shares sold at each separate price within the range set forth above.
( 3)  The price reported in Column 4 represents the weighted average price of multiple transactions with a range of prices between $10.33 to $10.49 inclusive. Mr. Kosloske undertakes to provide, upon request by the SEC, Health Insurance Innovations, Inc., or a security holder of Health Insurance Innovations, Inc., full information regarding the number of shares sold at each separate price within the range set forth above.
( 4)  By Lori Kosloske. Michael Kosloske and Lori Kosloske are husband and wife.
( 5)  This number of shares consists of 8,480,000 shares of Class B Common Stock held of record by Health Plan Intermediaries, LLC ("HPI") and 86,667 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. The shares of Class B Common Stock, together with the Series B Membership Interests of HPI, are exchangeable, at Mr. Kosloske's election, for equal numbers of shares of Class A Common Stock. This exchange right has no expiration date.

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 Chairman, President and CEO
Kosloske Lori
15438 N. FLORIDA AVENUE
SUITE 201
TAMPA, FL 33613
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/ Joan Rodgers, as Attorney-in-Fact 5/23/2014
** Signature of Reporting Person Date


Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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