Document:

Exhibit 10.16

 

SHARE
EXCHANGE AGREEMENT

 

This
Share Exchange Agreement (this “Agreement”) is entered into on November 22, 2021 between Progressive Care, Inc., a Delaware
corporation (the “Company”), and Yelena Braslavskya 2020 Gift Trust Dmitry Kristal Trustee (the “Shareholder”).

 

RECITALS

 

Shareholder
is the sole record
and beneficial
owner of all 51 of the issued and
outstanding shares
of the Series A Preferred Stock, par
value $0.001 per
share, of the Company
(the “Series A Stock”). Shareholder desires to exchange the shares
of Series A Stock owned by the Shareholder
for shares of
the Company’s common stock,
par value $0.0001
per share (“Common Stock”)
in an amount equal to 4.6% of the number of shares
of Common Stock issued and outstanding
as of the Effective Date
(as defined
below), on the terms and subject to
the conditions contained
herein (the “Share Exchange”).
The Company has
determined that the Share Exchange is
in the best interests of the parties and
have approved this Agreement and
the
transactions contemplated hereby.

 

TERMS
OF AGREEMENT

 

NOW,
THEREFORE, in consideration of the
foregoing and for
other good and valuable consideration,
the receipt and sufficiency of
which is
hereby acknowledged, the parties hereto
agree as follows:

 

1. Share
Exchange and Issuance. Subject to the terms and conditions
of this Agreement,
on the Effective Date, the Company shall
issue to Shareholder the number of
shares of Common Stock in an
amount equal to 4.6%
of the number of
shares of Common Stock issued and outstanding
as of the
Effective Date (the “Shares”)
and the Shareholder
will return the Series A Stock to the Company for cancellation and
return to treasury. The “Effective
Date” is the date immediately
preceding the date of the filing of
the final Amendment to Registration
Statement on Form S-1/A filed with the Securities and Exchange Commission
(the “Commission”)
pursuant to a Qualified Offering (as defined below) to precede such Registration Statement being declared effective
by the Commission.
“Qualified Offering”
means the closing of an underwritten
offering by the Company pursuant to which (1) the Company receives
aggregate gross proceeds
of at least $10 million in consideration of
the purchase of securities
(the “Offering Securities”)
or (2)
(a) the
Company receives
aggregate gross proceeds
of at least
$5 million
in consideration of the Offering Securities and (b)
the Common
Stock becomes
listed
on The
Nasdaq Capital Market,
the New York Stock Exchange, or the NYSE MKT (the
earlier to occur of (1) or (2) above,
the “Qualified
Offering”).
The Shareholder shall
deliver to
the Company all
certificates representing the shares
of Series A Stock owned by the Shareholder
properly endorsed
for cancellation and return
to treasury and the Company shall
issue to Shareholder a new certificate
(or book
entry statement) representing
the Shares.

 

    	 

     

    

 

2. Effect
of Exchange. The parties
hereto hereby acknowledge and agree
that all shares
of Series A Stock owned by Shareholder
shall be
cancelled as contemplated hereby
and Shareholder shall
be entitled
only to the
exchange of the shares
of Series A Stock held
by the Shareholder
for the
Shares
of Common Stock provided for herein.
Except as to
the rights
and obligations
of the
parties arising under
this Agreement and the
Shares issued to
Shareholder hereunder, each of the
parties hereto hereby forever releases,
surrenders, waives and abandons
any and all claims,
rights, obligations, rights of action
whether in contract or
tort, of
any and every type whatsoever, known
or unknown,
past, present or future
(expressly assuming all
risk thereof and associated therewith)
against the
other party, its officers, directors,
employees, shareholders, affiliates or other agents
or persons
acting on its
behalf arising solely from
the Shareholder’s prior
ownership of the
Series A Stock
and in
connection with the
Share Exchange.

 

3. Representations
of the Company. The Company
represents and
warrants to the Shareholder that:

 

(a) Organization
and Qualification. The Company is a
corporation duly organized,
validly existing and in good
standing under the laws of
the jurisdiction in which
it is incorporated,
with full
power
and authority (corporate and other)
to own,
lease, use and
operate its properties and
to carry on
its business as
and where now owned,
leased, used,
operated and conducted.

 

(b) Authorization;
Enforcement. (i) The Company has all
reqms1te corporate
power and
authority to enter
into and
perform this Agreement and
to consummate
the transactions contemplated hereby
and thereby
and to
issue and deliver
the Shares, in accordance with the
terms hereof,
(ii) the
execution and delivery of this Agreement
and the consummation by the Company
of the
transactions
contemplated hereby
have been duly authorized by
the Company’s Board
of Directors and no further
consent or authorization of the
Company, its
Board of Directors,
or its
shareholders is
required, (iii) this
Agreement has been
duly executed
and delivered by the
Company, and

 

(iv)
this Agreement constitutes
a legal,
valid and
binding obligations of the Company
enforceable against the
Company in
accordance with its
terms, except
as such
enforceability may be limited
by applicable bankruptcy,
insolvency or similar laws
affecting creditors rights
generally or
general principles
of equity.

 

(c) Issuance
of Shares. The Shares
have
been duly
authorized and upon
issuance will be
validly issued,
fully paid, and non-assessable
shares of the Company, and free
from all taxes,
liens, claims
and encumbrances
and shall not
be subject to preemptive
rights or other
similar rights of shareholders of
the
Company.

 

(d) No
Conflicts. The execution, delivery
and performance of this Agreement by
the Company and
the consummation
by the Company
of the transactions
contemplated hereby will
not (i)
conflict with or result
in a violation of any provision
of the
Certificate of Incorporation,
as amended, or
Bylaws. Neither the
Company nor
any of its
subsidiaries is
in violation of its Articles of Incorporation,
Bylaws, or other organizational documents
Except as specifically
contemplated by
this Agreement, the Company is not required to
obtain any consent, authorization or
order of, or make
any filing
or registration
with, any court, governmental agency,
regulatory agency,
self-regulatory
organization or stock
market or
any third party in order
for it to execute,
deliver or perform any
of its
obligations under
this Agreement in accordance with the
terms hereof and
to issue
the Shares.

 

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 (e) Covenants. The Company covenants to the Shareholder the following:

 

		1.	At
                                            Shareholder’s request, the
                                            Company will use
                                            commercially
                                            practicable
                                            efforts
                                            to
                                            provide, through counsel,
                                            at the Company’s
                                            expense,
                                            a
                                            Rule
                                            144 legal opinion
                                            to the Shareholder
                                            that
                                            is acceptable
                                            to
                                            the Shareholder in case
                                            the
                                            Shareholder
                                            will require one
                                            for
                                            the
                                            purpose of
                                            depositing
                                            the
                                            Shares
                                            with
                                            a
                                            clearing
                                            or
                                            brokerage firm for
                                            the
                                            purpose of
                                            liquidating all
                                            or a
                                            portion
                                            of
                                            the
                                            Shares.

 

		2.	The
                                            Company
                                            will
                                            provide
                                            all and
                                            any supporting and necessary
                                            documentation to the Shareholder or
                                            on behalf
                                            of
                                            the Shareholder
                                            for the purpose of
                                            clearing or registering
                                            the Shares.

 

4. Representations
of Shareholder. The Shareholder
represents and warrants to the
Company solely as to Shareholder
that:

 

(a) Ownership.
The Shareholder
is the sole record and beneficial
owner of
the shares
of Series A Stock and
such shares of Series
A Stock are free and clear of
any restrictions on
transfer, taxes, liens, options,
warrants, purchase rights,
contracts, commitments,
equities, claims, and demands.

 

(b) Investment
Purpose. The Shareholder is
acquiring the Shares for its own
account and not with
a present view towards the public
sale or
distribution thereof.

 

(c) Transfer
or Re-sale. The Shareholder understands that (i)
the issuance of
the Shares
has not been
and is not being registered under the
Securities Act of 1933,
as amended and the
rules and regulations
promulgated thereunder (the “1933
Act”) or any
applicable state
securities laws, and
the Shares may not be transferred except
pursuant to an
effective registration statement
or a
valid exemption from the registration
requirements of the 1933 Act, and
neither the Company
nor any
other person is under any
obligation to register the Shares under
the 1933 Act or any state
securities laws or
to comply
with the terms and
conditions of any
exemption thereunder.

 

(d) Legends.
The Shareholder understands
that the Shares will bear a restrictive
legend in substantially
the following
form (and a stop-transfer order
may be placed against transfer
of the certificate(s)
representing such Shares):

 

“The
securities represented by this
instrument have not been registered
under the Securities
Act of 1933,
as amended. The
securities may
not be sold,
transferred or
assigned in the absence
of an effective registration statement
for the securities
under said
Act, or an opinion of counsel, in
form, substance and
scope acceptable to the Company that
registration
is not required under
said Act.”

 

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(e) Authorization;
Enforcement. This Agreement has
been duly and validly authorized.
This Agreement
has been duly
executed and
delivered on behalf of
the Shareholder, and this Agreement
constitutes the valid
and binding agreement
of the Shareholder
enforceable in
accordance with its
terms, except as
such enforceability
may be limited by applicable bankruptcy, insolvency or
similar laws
affecting creditors rights generally
or general principles of equity.

 

5. Counterparts.
This Agreement may be
executed in any
number of
counterparts, .· each
of which shall
be an
original but all
of which together shall constitute
one and
the same
instrument.

 

6. Governing
Law.
This Agreement shall be
construed in
accordance with and
governed by
the laws of the State of Florida applicable
to contracts
executed and to
be wholly performed
within such State
(without regard
to the choice
of law
provisions thereof). Each party
hereby irrevocably and unconditionally
consents and
submits to
the exclusive jurisdiction
of the
courts of the
State of
Florida sitting in
Broward County, Florida,
and of the
United States District
Court for the Southern
District of Florida
for any actions, suits or proceedings
arising out
of or relating
to this Agreement and
the transactions
contemplated hereby and
each party
agrees not
to commence
any action, suit
or proceeding
relating thereto except
in such
courts. Each party
further agrees that any
service of process,
summons, notice
or document
sent by
U.S. registered mail
to its address set
forth herein
shall be
effective service
of process
for any action,
suit or proceeding
brought against it
in any such
court. Each party
irrevocably and unconditionally
waives any
objection to the laying of
venue of any
action, suit or
proceeding arising
out of this Agreement or the
transactions contemplated
hereby in such
courts, and irrevocably and unconditionally
waives and
agrees not
to plead
or claim in any
such court
that any
action, suit or
proceeding brought in any
such court has
been brought in
an inconvenient
forum.

 

7. Amendment.
This Agreement may
be amended
only by
the mutual agreement and written
consent of
the parties hereto.

 

[REMAINDER
OF PAGE INTENTIONALLY LEFT BLANK]

 

 

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IN
WITNESS WHEREOF, the parties hereto have caused this Agreement to be duly executed
and delivered as of the day and
year first written above.

 

	 	
PROGRESSIVE CARE, INC.
	 	 
	 	By:	 
	 	 	Alan Jay Weisberg

	 	 	Chief Executive Officer
	 	 	 
	 	SHAREHOLDER
	 	 
	 	 	 
	 	 	Yelena Braslavskya 2020 Gift Trust
	 	 	Dmitry
    Kristal, TrusteeExhibit
10.17

 

SETTLEMENT
AGREEMENT, WAIVER AND RELEASE OF CLAIMS

 

This
Settlement Agreement, Waiver and Release of Claims (this “Agreement”), dated January 20, 2022 (the “Effective
Date”), is entered into by and among Chicago Venture Partners, L.P., a Utah limited partnership (“CVP”),
Iliad Research and Trading, L.P., a Utah limited partnership (“Iliad”, and together with CVP, “Investors”),
and Progressive Care Inc., a Delaware corporation (“Company”). Each of CVP, Iliad and Company are sometimes individually
referred to hereinafter as a “Party” and collectively as the “Parties”.

 

A.
On January 2, 2019, Company sold and issued to CVP a certain Secured Convertible Promissory Note in the original principal amount of
$2,710,000.00 (the “CVP Note”) pursuant to a certain Securities Purchase Agreement between Company and CVP (the “CVP
Purchase Agreement,” and together with the CVP Note, and all other documents entered into in conjunction therewith, the “CVP
Financing Documents”).

 

B.
On March 6, 2019, Company sold and issued to Iliad a certain Secured Convertible Promissory Note in the original principal amount of
$3,310,000.00 (the “Iliad Note”) pursuant to a certain Securities Purchase Agreement between Company and Iliad (the
“Iliad Purchase Agreement,” and together with the Iliad Note, and all other documents entered into in conjunction
therewith, the “Iliad Financing Documents,” and together with the CVP Financing Documents, the “Financing
Documents”).

 

C.
The CVP Note and Iliad Note each contained provisions limiting the number of shares of common stock Investors could sell per week (the
“Volume Limitation Provisions”).

 

D.
As of end of day on the Effective Date, Iliad holds a certain number of shares of common stock of Company as shown on its brokerage statement
as of such date, and no other entity or individual affiliated with CVP or Iliad holds or has control over any shares.

 

E.
A dispute arose among the Parties with respect to the Volume Limitation Provisions.

 

F.
On December 14, 2021, Company caused a letter to be sent to Investors alleging a breach by
Investors of the Volume Limitation Provisions and making certain claims against Investors (the “Demand Letter”).

 

G.
As a result of a dispute regarding the claims raised in the Demand Letter, on or around January 7, 2022, Investors filed a lawsuit against
Company in the Third Judicial District Court of Salt Lake County, State of Utah (the “Lawsuit”), and on or around
January 7, 2022 Investors also sent Company an Arbitration Notice pursuant to the CVP Purchase Agreement and the Iliad Purchase Agreement
(the “Arbitration”).

 

H.
The Parties acknowledge and understand that Company will seek to obtain third-party financing, use some or all of those funds to repay
the Iliad Note, as modified by this Agreement, in full, and owe each other no further obligations.

 

I.
In order to resolve the Lawsuit, the Arbitration, and all other disputes between the Parties,the Parties have agreed, subject to the
terms and conditions set forth herein, to (i) resolve all disputes regarding the claims raised in the Demand Letter, (ii) dismiss the
Lawsuit and the Arbitration, and (iii) affirmatively conclude all obligations under the CVP Financing Documents.

 

    	 

     

    

 

NOW,
THEREFORE, in consideration of the promises set forth in this Agreement and for other good and valuable consideration, the receipt and
sufficiency of which are hereby acknowledged, the Parties agree as follows:

 

1.
Incorporation of Recitals. The foregoing recitals are contractual in nature and are incorporated herein as part of this Agreement.

 

2.
Extension of Maturity Date. Iliad and Company agree that the maturity date of the Iliad Note
is hereby extended to April 15, 2022. Company is also granted the right to extend the maturity date of the Iliad Note for an additional
month to May 15, 2022 at its election by providing written notice of such election to Iliad. In the event Company elects to extend the
maturity date to May 15, 2022, then the outstanding balance of the Iliad Note will automatically increase by two percent (2%).

 

3.
Standstill.

 

3.1.
Standstill Period. So long as no event of default occurs under the Iliad Note, Iliad and any entity affiliated with Iliad agrees not
to sell any shares of Company’s common stock for the period (the “Standstill Period”) beginning on the Effective
Date and ending on the maturity date of the Iliad Note (as amended by this Agreement). In addition, Iliad agrees not to submit any Redemption
Notices (as defined in the Iliad Note) under the Iliad Note during the Standstill Period (so long as no event of default occurs under
the Iliad Note). For the avoidance of doubt, nothing in this Agreement alters the Volume Limitation set forth in the Note, or Iliad’s
obligation to observe the Volume Limitation after the Standstill Period. The Parties will submit a letter in the form attached as Exhibit
A to ClearTrust. The Parties will also prepare a letter to ClearTrust in the form attached as Exhibit B, which will be held by Company.
If the Company submits this letter to ClearTrust, that will be considered an election to extend the maturity date to May 15, 2022, as
set forth in Section 2 above.

 

3.2.
Monitoring of the Standstill. Up to once per week, Company may request via email to John Fife (jfife@chicagoventure.com), Chris
Stalcup (cstalcup@chicagoventure.com) and Leo Hansen (lhansen@chicagoventure.com), a document sufficient to show the number of
shares of Company’s common stock held by Iliad. This document shall be a statement or report prepared by Iliad’s
stockbroker and may be a printout or screenshot of that stockbroker’s website portal, showing Iliad’s holdings at the
close of trading on that date. Iliad shall have two trading days to deliver such report after the day on which it is requested. If
the document is not produced timely, the balance of the Iliad Note shall reduce by $500 each trading day that Iliad fails to deliver
the document (the “Monitoring Fee”). On the seventh trading day after a request, if the request has not yet been
honored, the Monitoring Fee will be increased to $1,000 per trading day. Company must provide written notice to Iliad in the event
the cumulative amount of Monitoring Fees assessed under this Section 3.2 reaches $10,000. In addition, within thirty (30) days of
the end of the Standstill Period, Company must notify Iliad of the amount of Monitoring Fees it believes has accrued. In the event
Company fails to provide such accounting within the applicable time period, all Monitoring Fees will be waived. The Monitoring Fees
are intended to act as liquidated damages and will be Company’s sole exclusive remedy for Iliad’s breach of this Section
3.2.

 

4.
CVP Payment. CVP agrees to pay Company $175,000.00 via wire transfer of immediately available funds within two (2) business days of the
Effective Date (the “CVP Payment”).

 

5.
CVP Financing Documents. Upon Company’s receipt of the CVP Payment, the Parties agree that all of the CVP Financing Documents will
be deemed to be terminated and of no further force or effect. The Parties agree that the Iliad Financing Documents will remain in full
force and effect (as modified pursuant to the terms of this Agreement).

 

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6.
Iliad Financing Documents. Iliad acknowledges a decrease in the balance of the Iliad Note, effective as of May 31, 2021, of $180,000
with the result that, on the Effective Date, the outstanding balance of the Iliad Note (following the foregoing balance reduction) is
$2,155,638.63, consisting of $1,310,744.54 of principal and $844,894.09 of interest and other financing charges. In the event the Iliad
Note is not repaid by February 16, 2022, the outstanding balance of the Iliad Note will increase in the amount of $100,000.

 

7.
Prepayment. The last sentence of Section 1.2 of the Iliad Note shall be deleted in its entirety and replaced with the following:

 

“If
Borrower exercises its right to prepay this Note, Borrower shall make payment to Lender of an amount in cash equal to 105% of the portion
of the Outstanding Balance Borrower elects to repay (the “Prepayment Amount”). Borrower shall also have the right
to treat up to ten percent (10%) of the Prepayment Amount as a Conversion and satisfy such portion of the Prepayment Amount by delivering
Conversion Shares to Lender (subject to the Maximum Percentage (as defined below).”

 

8.
Representations and Warranties.

 

8.1.
Representations and Warranties of Company. As a material inducement to Investors to enter into this Agreement, Company represents and
warrants to Investors as follows:

 

(a)
Authority for Agreement. Company has full power, authority and legal right and capacity to enter into and perform Company’s obligations
under this Agreement and each other document contemplated hereby to which Company is or will be a party and to consummate the transactions
contemplated hereby and thereby. Company has approved this Agreement and the other documents contemplated hereby and the transactions
contemplated hereby and thereby and has authorized the execution, delivery and performance of this Agreement and the other documents
contemplated hereby and the consummation of the transactions contemplated hereby and thereby. No other proceedings on the part of Company,
whether by the officers, directors, shareholders, or otherwise, are necessary to approve and authorize the execution, delivery and performance
of this Agreement and the other documents contemplated hereby and the consummation of the transactions contemplated hereby and thereby.
This Agreement and the other documents contemplated hereby to which Company is a party have been duly executed and delivered by Company
and are legal, valid and binding obligations of Company, enforceable against Company in accordance with their respective terms.

 

(b)
No Violation to Result. The execution, delivery and performance by Company of this Agreement and the other documents contemplated hereby
and the consummation by Company of the transactions contemplated hereby and thereby, do not and will not, directly or indirectly (with
or without notice or lapse of time), violate, breach, conflict with, constitute a default under, accelerate or permit the acceleration
of the performance required by any note, debt instrument, security agreement, mortgage or any other contract to which Company is a party
or by which Company is bound. Except for a current report on Form 8-K, no notice to, filing with, or consent of, any person is necessary
in connection with the execution, delivery or performance by Company of this Agreement and the other documents contemplated hereby nor
the consummation by Company of the transactions contemplated hereby or thereby. Company has given all notices, made all filings (other
than a current report on Form 8-K) and obtained all consents necessary for the consummation of the transactions contemplated herein.

 

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8.2.
Representations and Warranties of Investors. As a material inducement to Company to enter into this Agreement, each Investor represents
and warrants to Company with respect to itself as follows:

 

(a)
Authority for Agreement. Each Investor has full power, authority and legal right and capacity to enter into and perform such Investor’s
obligations under this Agreement and each other document contemplated hereby to which such Investor is or will be a party and to consummate
the transactions contemplated hereby and thereby. Each Investor has approved this Agreement and the other documents contemplated hereby
and the transactions contemplated hereby and thereby and has authorized the execution, delivery and performance of this Agreement and
the other documents contemplated hereby and the consummation of the transactions contemplated hereby and thereby. No other proceedings
on the part of Investors, whether by the officers, directors, stockholders, or otherwise, are necessary to approve and authorize the
execution, delivery and performance of this Agreement and the other documents contemplated hereby and the consummation of the transactions
contemplated hereby and thereby. This Agreement and the other documents contemplated hereby to which Investors are a party have been
duly executed and delivered by Investors and are legal, valid and binding obligations of Investors, enforceable against Investors in
accordance with their respective terms.

 

(b)
No Violation to Result. The execution, delivery and performance by such Investor of this Agreement and the other documents contemplated
hereby and the consummation by such Investor of the transactions contemplated hereby and thereby, do not and will not, directly or indirectly
(with or without notice or lapse of time), violate, breach, conflict with, constitute a default under, accelerate or permit the acceleration
of the performance required by any note, debt instrument, security agreement, mortgage or any other contract to which such Investor is
a party or by which such Investor is bound. No notice to, filing with, or consent of, any person is necessary in connection with the
execution, delivery or performance by such Investor of this Agreement and the other documents contemplated hereby nor the consummation
by such Investor of the transactions contemplated hereby or thereby. Each Investor has given all notices, made all filings and obtained
all consents necessary for the consummation of the transactions contemplated herein.

 

(c)
Recital D. Recital D is true and correct.

 

9.
Mutual Release.

 

9.1.
Release by Investors. Each Investor, on behalf of itself and its managers, members, officers, employees, general partners, limited partners,
agents, attorneys, successors and assigns, and any and all past and present such persons (collectively, the “Investor Parties”),
forever relieves, releases and discharges Company and its directors, stockholders, officers, employees, agents, attorneys, successors
and assigns, and any and all past and present such persons (collectively, the “Company Parties”), from any and all
claims, counterclaims, defenses, affirmative or otherwise, rights of setoff, rights of recoupment, debts, liabilities, demands, obligations,
promises, acts, agreements, costs and expenses (including, but not limited to, attorneys’ fees), damages, injuries, actions and
causes of actions, of whatever kind or nature, whether legal or equitable, known or unknown, suspected or unsuspected, contingent or
fixed (each a “Claim”, and collectively, the “Claims”), that such Investor or any of the Investor
Parties may have that are based upon, relate to or arise out of the Lawsuit, the Arbitration, the Financing Documents, or any transaction
contemplated by the Parties under the Financing Documents, arising or accruing before the Effective Date. Such release will not apply
to or affect any breach of the Iliad Financing Documents or this Agreement after the Effective Date. Such release will also not affect
Company’s obligation to fulfill its remaining obligations under this Agreement or the Iliad Transaction Documents as modified by
this Agreement.

 

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9.2.
Release by Company. Company, on behalf of itself and Company Parties, forever relieves, releases and discharges each Investor and the
Investor Parties, from any and all Claims that Company or any of Company Parties may have that are based upon, or directly or indirectly
arising out of or relate to the Lawsuit, the Arbitration, the transactions contemplated hereby, or any claims that were raised or could
have been raised in the Demand Letter, the Financing Documents, or any transaction contemplated by the Parties under the Financing Documents,
arising or accruing before the Effective Date. Company hereby acknowledges and agrees that the execution of this Agreement by Iliad shall
not constitute an acknowledgment of or admission by Iliad of the existence of any claims or of liability for any matter or precedent
upon which any claim or liability may be asserted. Such release will not apply to or affect any breach of the Iliad Financing Documents
or this Agreement after the Effective Date. Such release will also not affect Iliad’s obligation to fulfill its remaining obligations
under this Agreement or the Iliad Transaction Documents as modified by this Agreement. Company hereby acknowledges and agrees that in
the event Company issues any shares of its common stock to Iliad under the Iliad Note, that the releases set forth above in this paragraph
9.2 apply to the issuance of those shares, and Company may not use such issuance of shares to raise, use or rely on any of the claims
in the Demand Letter or any other similar claims as a defense to repayment of the Iliad Note or to rescind the Iliad Note. In exchange
for the mutual covenants and promises herein, Company agrees, now and in the future, not to raise, rely on or use any of the Claims waived
herein, or any similar claims in an attempt to rescind the Iliad Note, as a defense to repayment of the Iliad Note, or to otherwise modify
the Iliad Note or Company’s obligations thereunder.

 

9.3.
Release Representations. Each Party hereto, for itself and on behalf of such Party’s other respective releasing parties, represents,
warrants and agrees that (a) such Party waives Claims as set forth above, (b) such Party covenants not to institute against any of the
parties it is releasing hereunder any proceeding, suit or action, at law or in equity, of whatsoever kind or nature, or in any way to
aid in or encourage the institution or prosecution thereof, for damages, expenses, compensation, injunctive relief or otherwise, arising
from or based upon any Claim, except that nothing herein shall restrict a Party from making statements to a government official in good
faith or from offering testimony in any legal action (c) none of the Claims such Party is releasing and waiving hereunder have been sold,
assigned or otherwise transferred or encumbered (directly or indirectly) to any person or party whatsoever, (d) such Party has the full
right and power to grant, execute and deliver the full and complete release and waiver contained herein, and (e) the release made by,
and the representations, warranties, and covenants of the other Parties hereto, are accepted by each Party hereto as a material inducement
to entering into and consummating the transactions contemplated by this Agreement.

 

9.4.
Unknown Claims. Each Party hereto represents that it is not aware of any claim against or involving any Party it is releasing hereunder
other than the Claims, all of which are released hereunder. Each Party hereto acknowledges that it has been advised by legal counsel
and is familiar with the legal principle that provides that a general release does not extend to claims which the releasor does not know
or suspect to exist in its favor at the time of executing the release, which if known by it must have materially affected its settlement
with the releasee. Each Party hereto, being aware of said principle, agrees to expressly waive any rights to this effect, as well as
under any other statute or common law principles of similar effect.

 

10.
Dismissals. The Parties agree to cause the Lawsuit and the Arbitration
to be dismissed. The Parties further agree to cooperate with each other to the extent reasonably necessary in the filing of the dismissal
documents and to take all reasonable additional steps necessary to effectuate the dismissal of the Lawsuit and the Arbitration. For the
avoidance of doubt, the foregoing dismissal will not prevent Investor or Company from bringing a new lawsuit and/or arbitration for breaches
of this Agreement or the Iliad Financing Documents.

 

11.
Effect of Breach. The Parties agree that the affirmative obligations which each Party has undertaken in this Agreement are a material
inducement to the other Parties entering into this Agreement. In the event of a breach of this Agreement, the breaching Party agrees
that the non-breaching Party shall be entitled to temporary and permanent injunctive relief to enforce the provisions hereof, and that
such relief may be granted without the necessity of proving actual damages. This provision with respect to injunctive relief shall not,
however, diminish the right of the Parties to claim and recover damages, or to seek and obtain any other relief available to it at law
or in equity, in addition to injunctive relief.

 

    	5

     

    

 

12.
Liquidated Damages. In the event that Iliad, during the Standstill Period, breaches its obligations in Section 3.1 (which breach
cannot be cured); Company shall be entitled to liquidated damages. The Parties acknowledge that a breach as set forth in this paragraph
is likely to put Company’s planned financing and stock market listings at risk, which will result in damages that are difficult
or impossible to calculate. In the event of such a breach, the parties agree that an approximate measure of these damages will be 300%
of the value of the shares sold in violation of the standstill set forth in Section 3.1, and agree to this figure as liquidated damages.
The foregoing liquidated damages will be Company’s sole and exclusive remedy for a breach of Section 3.1.

 

13.
Miscellaneous.

 

13.1.
No Admission of Liability. This Agreement shall not be construed as an admission by any Party of any validity or invalidity of
such Party’s claims or defenses in any action or proceeding. Neither this Agreement’s terms nor the fact of this Agreement
shall be offered or received in evidence or be admissible for any reason in any form in any action or proceeding in any court or tribunal
(other than an action to enforce the terms hereof), or used, publicized or disclosed in any manner as an admission, concession or evidence
of any liability or wrongdoing of any nature by any Party. The obligations of the Investors hereunder shall be several and not joint.

 

13.2.
Further Assurances. At any time or from time to time after the Effective Date, at the request of a Party, and without further consideration,
each of the Parties shall execute and deliver, or shall cause its respective affiliate(s) to execute and deliver, such other agreements,
instruments, certifications or other documents as may be necessary or desirable to effectuate the transactions and fulfill its obligations
under this Agreement.

 

13.3.
Governing Law; Venue. This Agreement shall be construed and enforced in accordance with, and all questions concerning the construction,
validity, interpretation and performance of this Agreement shall be governed by, the internal laws of the State of Utah, without giving
effect to any choice of law or conflict of law provision or rule (whether of the State of Utah or any other jurisdictions) that would
cause the application of the laws of any jurisdictions other than the State of Utah. Each of the Parties consents to the exclusive personal
jurisdiction of the federal courts whose districts encompass any part of Salt Lake County, Utah or the state courts of the State of Utah
sitting in Salt Lake County, Utah in connection with any dispute arising under this Agreement, and hereby waives, to the maximum extent
permitted by law, any objection, including any objection based on forum non conveniens, to the bringing of any such proceeding in such
jurisdictions or to any claim that such venue of the suit, action or proceeding is improper. Nothing in this subsection shall affect
or limit any right to serve process in any other manner permitted by law.

 

13.4.
Waiver of Jury Trial. EACH PARTY TO THIS AGREEMENT IRREVOCABLY WAIVES ANY AND ALL RIGHTS SUCH PARTY MAY HAVE TO DEMAND THAT ANY ACTION,
PROCEEDING OR COUNTERCLAIM ARISING OUT OF OR IN ANY WAY RELATED TO THIS AGREEMENT OR THE RELATIONSHIPS OF THE PARTIES HERETO BE TRIED
BY JURY. THIS WAIVER EXTENDS TO ANY AND ALL RIGHTS TO DEMAND A TRIAL BY JURY ARISING UNDER COMMON LAW OR ANY APPLICABLE STATUTE, LAW,
RULE OR REGULATION. FURTHER, EACH PARTY HERETO ACKNOWLEDGES THAT SUCH PARTY IS KNOWINGLY AND VOLUNTARILY WAIVING SUCH PARTY’S RIGHT
TO DEMAND TRIAL BY JURY.

 

    	6

     

    

 

13.5.
Severability. If any part of this Agreement is construed to be in violation of any law, such part shall be modified to achieve the objective
of the Parties to the fullest extent permitted and the balance of this Agreement shall remain in full force and effect.

 

13.6.
Successors. This Agreement shall be binding upon the Parties and their respective heirs, legal representatives, successors and assigns
and shall inure to the benefit of the Parties and their respective heirs, successors and assigns.

 

13.7.
Amendment and Waiver. The provisions of this Agreement may be amended and waived only with the prior written consent of the Parties to
which such amendment and/or waiver applies.

 

13.8.
En tire Agreement. This Agreement, together with the Financing Documents and all other documents contemplated herein, constitutes the
sole and entire agreement between the Parties, whether written or oral, relating to the subject matter hereof and thereof. This Agreement
may only be amended by the Parties in writing.

 

13.9.
Expenses. Each Party shall pay its own legal fees and expenses incurred with respect to the Lawsuit, the Arbitration, the negotiation
and drafting of this Agreement, and the transactions contemplated hereby.

 

13.10.
Attorneys’ Fees. In the event of any action at law or in equity to enforce or interpret the terms of this Agreement or any document
executed in connection herewith, the Parties agree that the prevailing party shall be entitled to an award of the full amount of the
attorneys’ fees and expenses paid by such prevailing party in connection with the litigation and/or dispute without reduction or
apportionment based upon the individual claims or defenses giving rise to the fees and expenses. Nothing herein shall restrict or impair
a court’s power to award fees and expenses for frivolous or bad faith pleading.

 

13.11.
Notices. Any notice required or permitted hereunder shall be given in writing (unless otherwise specified herein) and shall be deemed
effectively given on the earliest of: (a) the date delivered, if delivered by personal delivery as against written receipt therefor or
by email to an executive officer, (b) the date delivered after deposit, postage prepaid, in the United States Postal Service by certified
mail, or (c) the date delivered by express courier, with delivery costs and fees prepaid, in each case, addressed to each of the other
parties thereunto entitled at the following addresses (or at such other addresses as such party may designate by five (5) calendar days’
advance written notice similarly given to each of the other parties hereto):

 

If
to Company:

 

Progressive
Care Inc.

Attn:
Jay Weisberg

400
Ansin Blvd., Suite A Hallandale Beach, Florida 33009

 

    	7

     

    

 

With
a copy to (which copy shall not constitute notice):

 

Shendell
& Pollock, P.L. Attn: Gary Shendell

2500
N. Military Trail, Suite 150 Boca Raton, Florida 33431

 

Pia
Hoyt, LLC

Attn:
John P. Mertens

136
E South Temple, Suite 1900 Salt Lake City, Utah 84111

 

If
to Investors:

 

Chicago
Venture Partners, L.P. Iliad Research and Trading, L.P.

Attn: John Fife

303
East Wacker Drive, Suite 1040

Chicago,
Illinois 60601

 

With
a copy to (which copy shall not constitute notice):

 

Hansen
Black Anderson Ashcraft PLLC

Attn: Jonathan K. Hansen

3051
West Maple Loop, Suite 325

Lehi, Utah 84043

 

13.12.
Counterparts. This Agreement may be signed in one or more counterparts, which together shall constitute one document. Additionally, facsimile
signatures or signatures conveyed via e- mail in one or more counterparts of this Agreement shall be binding.

 

13.13.
Indemnification. In the event Company or an Investor breaches any of its warranties or covenants contained in this Agreement, the breaching
party agrees to indemnify all others against all losses, claims, damages, liabilities, and expenses (including attorneys’ fees)
caused by such breach. The Parties also agree to indemnify each other against all losses, claims, damages, liabilities, and expenses
(including attorneys’ fees) caused by or related to any untrue representation made by any Party in Section 8 of this Agreement,
or through the filing of a Claim waived under this Agreement.

 

13.14.
Third Party Beneficiaries. Except as expressly set forth herein, nothing in this Agreement, express or implied, is intended to confer
upon any person, other than the Parties, any rights, remedies, obligations, or liabilities of any nature whatsoever.

 

13.15.
Acknowledgement. By executing this Agreement, each of the Parties evidences that it carefully read and fully understands all of the provisions
of this Agreement. Each Party further acknowledges that, in executing this Agreement, it has not relied on any promise of future benefit
or any statement of any of the Parties, or anyone representing any of the Parties, whether written or oral, not set forth in this Agreement.

 

13.16.
Time is of the Essence. Time is expressly made of the essence with respect to each and every provision of this Agreement.

 

13.17.
Construction; Joint Drafting. The Parties acknowledge that they have participated jointly in the negotiation and drafting of this Agreement
and, in the event an ambiguity or question of intent or interpretation arises, this Agreement shall be construed consistent with the
joint drafting of this Agreement by the parties and no presumption or burden of proof shall arise favoring or disfavoring any party by
virtue of the authorship of any of the provisions of this Agreement.

 

[Remainder
of page intentionally left blank; signature page to follow]

 

    	8

     

    

 

IN
WITNESS WHEREOF, the undersigned have executed this Agreement to be effective as of the Effective Date.

 

	 	INVESTORS:
	 	 
	 	CHICAGO
    VENTURE PARTNERS, L.P.
	 	 	 
	 	By:	Chicago
    Venture Management, L.L.C., its General Partner
	 	 	 
	 	By:	CVM,
    Inc., its Manager
	 	 	 
	 	By:	
	 	 	John
    M. Fife, President
	 	 	 
	 	ILIAD
    RESEARCH AND TRADING, L.P.
	 	 	 
	 	By:	Iliad Management, LLC, its General Partner

                                                         

                                                         

	 	 	 
	 	By:	 Fife Trading, Inc., its Manager
	 	 	 
	 	By:	
	 	 	John
    M. Fife, President
	 	 	 
	 	COMPANY:
	 	 
	 	PROGRESSIVE
    CARE INC.
	 	 	 
	 	By:	
	 	 	Jay
    Weisberg, Chief Executive Officer

 

[Signature
Page to Settlement Agreement, Waiver, and Release of Claims]

 

    	 

     

    

 

Exhibit
A

 

ILIAD
RESEARCH AND TRADING, L.P.

303
East Wacker Drive, Suite 1040

Chicago,
Illinois 60601

 

ClearTrust,
LLC

16540
Pointe Village Drive, Suite 205

Lutz,
FL 33558

 

Ladies
and Gentlemen:

 

Reference
is made to the letter (“Letter”) of March 6, 2019 sent to you by Shital Parikh Mars on behalf of Progressive
Care, Inc. (“Progressive”). The instructions set forth in the Letter are to be suspended, effective immediately,
until April 16, 2022. Progressive and Iliad Research and Trading, L.P. (“Iliad”) have agreed that, until that
date, Iliad will not submit any further Conversion Notices.

 

The
instructions will resume on April 16, 2022 unless, prior to that time, the Note referenced in the Letter has been paid in full and you
have received a copy of the cancelled Note from Iliad.

 

	 	Very
    Truly Yours,
	 	 
	 	Iliad
    Research and Trading, L.P.
	 	By:	Iliad
    Management, LLC, its General Partner
	 	By:	Fife
    Trading, Inc., its Manager
	 	 	 
	 	By:	
	 	 	John
    M. Fife, President

 

	Acknowledged
                                            and Agreed:

 

Progressive
Care, Inc.

	 
	 	 	 
	By:	
	 	Jay
    Weisberg, Chief Executive Officer	 
	 	 	 
	Acknowledged
                                            and Agreed:

 

ClearTrust,
LLC

	 
	 	 	 
	By:		 

 

[Exhibit
to Settlement Agreement, Waiver, and Release of Claims]

 

    	 

     

    

 

Exhibit
B

 

ILIAD
RESEARCH AND TRADING, L.P.

303
East Wacker Drive, Suite 1040

Chicago,
Illinois 60601

 

ClearTrust,
LLC

16540
Pointe Village Drive, Suite 205

Lutz,
FL 33558

 

Ladies
and Gentlemen:

 

Reference
is made to the letter (“Letter”) of March 6, 2019 sent to you by Shital Parikh Mars on behalf of Progressive
Care, Inc. (“Progressive”). The instructions set forth in the Letter are to be suspended, effective immediately,
until May 16, 2022. Progressive and Iliad Research and Trading, L.P. (“Iliad”) have agreed that, until that
date, Iliad will not submit any further Conversion Notices.

 

The
instructions will resume on May 16, 2022 unless, prior to that time, the Note referenced in the Letter has been paid in full and you
have received a copy of the cancelled Note from Iliad.

 

	 	Very
    Truly Yours,
	 	 	 
	 	Iliad
    Research and Trading, L.P.
	 	By:	Iliad
    Management, LLC, its General Partner
	 	By:	Fife
    Trading, Inc., its Manager
	 	 	 
	 	By:	
	 	 	John
    M. Fife, President

 

	Acknowledged
    and Agreed:	 
	 	 	 
	Progressive
    Care, Inc.	 
	 	 
	By:	 	
	 	Jay
    Weisberg, Chief Executive Officer	 
	 	 	 
	Acknowledged
                                            and Agreed:

                                                                      

                                                                     ClearTrust,
                                            LLC
	 
	 	 	 
	By:	 	 

 

[Exhibit
to Settlement Agreement, Waiver, and Release of Claims]

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