Exhibit 99.1

NEITHER THIS DEBENTURE NOR THE SECURITIES INTO WHICH THIS DEBENTURE IS CONVERTIBLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE. THESE SECURITIES HAVE BEEN ISSUED OR SOLD TO THE HOLDER HEREOF IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES ACT OR PURSUANT TO AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS.

NAVIOS MARITIME HOLDINGS INC.

CONVERTIBLE DEBENTURE

No. NM - 1

FOR VALUE RECEIVED, NAVIOS MARITIME HOLDINGS INC., a corporation incorporated under the laws of the Republic of the Marshall Islands (the “Company”), hereby promises to pay to Navios Shipmanagement Holdings Corporation or its registered and permitted assigns (the “Holder”) the amount set out above as the Original Principal Amount, as the same may be reduced pursuant to the terms hereof upon conversion or otherwise, or increased pursuant to the terms hereof contemplating payment of PIK Interest (as defined below) or Loan Agreement Increase Events (as defined below) (as so reduced or increased, the “Principal Amount”) when due, on the Maturity Date (as defined below), upon acceleration or otherwise (in each case in accordance with the terms hereof) and to pay interest (the “Interest”) on any outstanding Principal Amount at the applicable Interest Rate (as defined below) from the date set out above as the Issuance Date (the “Issuance Date”) until the same becomes due and payable, whether upon the Maturity Date, acceleration, conversion or otherwise (in each case in accordance with the terms hereof).

This Convertible Debenture (including all Convertible Debentures issued in exchange, transfer or replacement hereof, this “Debenture”) is issued pursuant to the terms of the Loan Agreement originally entered into between the Company and the Holder on August 29, 2019, as amended and restated on December 13, 2021 (the “Amended and Restated 2019 Loan Agreement”) and the Loan Agreement originally entered into on June 29, 2021, as amended and restated on December 13, 2021 (the “Amended and Restated 2021 Loan Agreement” and, together, the “Loan Agreements”). All capitalized terms used in this Debenture but not otherwise defined herein have the meanings set forth in Section 7.

SECTION 1 - GENERAL TERMS

On the Maturity Date, the Company shall pay the Holder an amount in immediately available funds denominated in United States dollars representing all the outstanding Principal Amount and accrued and unpaid Interest to but excluding such date. The “Maturity Date” shall be January 3^rd, 2027 or such later date requested by the Company as the Holder may agree in its absolute discretion. Other than as expressly permitted by this Debenture, the Company may not prepay or redeem any portion of the outstanding Principal Amount without the prior written consent of the Holder.

Upon the happening of any event or circumstance subsequent to the Issuance Date pursuant to which, under the terms of either or both Loan Agreements, the Principal Amount of this Debenture shall be deemed to be increased (including but not limited to as a result of the election by the Company to not pay all or a portion of the interest due in cash under either or both such Loan Agreements) (each, a “Loan Agreement Increase Event”), the Principal Amount of this Debenture shall be deemed increased by the principal amount contemplated as of the relevant date under the terms of the applicable Loan Agreement(s).

The Holder and the Company shall maintain records showing any such increases in the Principal Amount as a result of Loan Agreement Increase Events under this Section 1(b), as well as increases in the Principal Amount as a result of PIK Interest under Section 1(c), and decreases in the Principal Amount and Interest as a result of conversions pursuant to Sections 2 or 3, and the dates of any such increases or decreases, in order to facilitate conversions of this Debenture from time to time pursuant to its terms without physical surrender.

1

Interest shall accrue daily on the outstanding balance of the Principal Amount at a rate equal to 4% per annum (“Interest Rate”) from the Issuance Date to (but excluding) the Maturity Date (or sooner if upon conversion or acceleration by the Holder as provided herein). Interest will be payable quarterly in arrears on the same dates on which interest payments are due and payable under the Loan Agreements, in each case by adding the accrued amounts of Interest to the then outstanding Principal Amount due under this Debenture (the “PIK Interest”). Interest will be payable to the Holder or its registered and permitted assignee. Notwithstanding any other provision of this Debenture, Interest that is paid in the form of PIK Interest in the manner specified in this Section 3(c) shall be considered paid, and shall not be considered overdue. Interest shall be calculated on the basis of a year of 365 or 366 days, as the case may be, and actual days elapsed during the period.

The Company has issued this Debenture as part of a unit with 1,000 shares of Series I Non-Economic Preferred Stock of the Company (the “Series I Preference Shares”) reflecting the terms set forth in the Certificate of Designation, Preferences and Rights of the Series I Preference Shares of the Company. The Series I Preference Shares are not detachable from this Debenture and this Debenture (or, if less than the entire outstanding Principal Amount is to be sold, assigned or otherwise transferred, the relevant portion hereof) accordingly may not be sold, assigned or otherwise transferred except in conjunction with a simultaneous sale of (or, as applicable, a proportional portion of) the Series I Preference Shares.

SECTION 2 - EVENTS OF DEFAULT

An “Event of Default”, wherever used herein, means any one of the following events (whatever the reason and whether it shall be voluntary or involuntary or effected by operation of law or pursuant to any judgment, decree or order of any court, or any order, rule or regulation of any administrative or governmental body):

2

During the time that any portion of this Debenture is outstanding, if any Event of Default has occurred and is continuing, the full unpaid Principal Amount of this Debenture, together with interest and other amounts owing in respect thereof, to the date of acceleration shall become at the Holder’s election, immediately due and payable in immediately available funds denominated in United States dollars; provided, however, the Holder may request (but shall have no obligation to request) payment of such amounts in Common Stock of the Company. If an Event of Default occurs and, following written notice from each Holder to the Company, for so long thereafter following such notice as such Event of Default remains uncured, without duplication of any default interest otherwise payable under the terms of the Loan Agreements, the Interest Rate on this Debenture shall immediately increase by 2% per annum in excess of the interest rate specified in Section 1(c) to the extent lawful and shall remain at such increased interest rate until the applicable Event of Default is cured. Furthermore, in addition to any other remedies, the Holder shall have the right (but not the obligation) to convert this Debenture at any time (x) after the occurrence and during the continuance of an Event of Default at the Conversion Price then in effect or (y) on or after the Maturity Date at the Conversion Price then in effect. The Holder need not provide and the Company hereby waives any presentment, demand, protest or other notice of any kind (other than required notice of conversion) and the Holder may immediately and without expiration of any grace period enforce any and all of its rights and remedies hereunder and all other remedies available to it under applicable law. Such declaration may be rescinded and annulled by Holder at any time prior to payment hereunder. No such rescission or annulment shall affect any subsequent Event of Default or impair any right consequent thereon.

SECTION 3 - CONVERSION OF DEBENTURE

This Debenture shall be convertible into shares of the Company’s Common Stock, on the terms and conditions set forth in this Section 3.

At any Trading Day on or after the Issuance Date, on one or more occasions, the Holder shall be entitled to convert, at its option, any Conversion Amount into fully paid and non-assessable shares of Common Stock in accordance with this Section 3.

At any time at or following the repayment in full of both Loan Agreements, if the VWAP per share of Common Stock is greater than the Mandatory Conversion Price for each of at least twenty (20) Trading Days in any period of thirty (30) consecutive Trading Days (such thirty (30) consecutive Trading Day period, the “Trading Period”), the Company may elect to convert (a “Mandatory Conversion”) the entire Principal Amount and accrued Interest (to but excluding the Mandatory Conversion Date (as defined below)) of this Debenture (in whole but not in part) into shares of Common Stock (the date selected by the Company for any Mandatory Conversion pursuant to this Section 3(b), the “Mandatory Conversion Date”).

3

4

SECTION 4 - ADJUSTMENTS TO CONVERSION PRICE AND MANDATORY CONVERSION PRICE; PRO RATA DISTRIBUTIONS

The Conversion Price shall be subject to adjustment from time to time as follows:

Whenever there is an adjustment pursuant to this Section 4, the Company shall promptly mail to the Holder a notice setting forth the Conversion Price and the Mandatory Conversion Price after such adjustment and setting forth a brief statement of the facts requiring such adjustment.

During such time as this Debenture is outstanding, if the Company shall declare or make any dividend whether or not permitted, or make any other distribution of its assets (or rights to acquire its assets) to holders of shares of Common Stock, by way of return of capital or otherwise (including, without limitation, any distribution of cash, stock or other securities, property or options by way of a dividend, spin off, reclassification, corporate rearrangement, scheme of arrangement or other similar transaction) (a “Distribution”), then, in each such case, the Holder shall be entitled to participate in such Distribution to the same extent that the Holder would have participated therein if the Holder had held the number of shares of Common Stock acquirable upon conversion of this Debenture immediately before the date of which a record is taken for such Distribution (or, if no such record is taken, the date as of which the record holders of shares of Common Stock are to be determined for the participation in such Distribution).

5

SECTION 5 - REISSUANCE OF THIS DEBENTURE

If this Debenture is to be transferred, the Holder shall surrender this Debenture to the Company, whereupon the Company will, subject to Section 5(e), forthwith issue and deliver upon the order of the Holder a new Debenture (in accordance with Section 5(d)), registered in the name of the registered transferee or assignee, representing the outstanding Principal Amount being transferred by the Holder and, if less than the entire outstanding Principal Amount is being transferred, a new Debenture (in accordance with Section 5(d)) to the Holder representing the outstanding Principal Amount not being transferred. Upon accepting this Debenture, the Holder and any assignee acknowledge and agree that, by reason of conversion of any portion of this Debenture, the outstanding Principal Amount represented by this Debenture may be less than the Principal Amount stated on the face of this Debenture.

Upon receipt by the Company of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this Debenture, and, in the case of loss, theft or destruction, of any indemnification undertaking by the Holder to the Company in customary form and, in the case of mutilation, upon surrender and cancellation of this Debenture, the Company shall execute and deliver to the Holder a new Debenture (in accordance with Section 5(d)) representing the outstanding Principal Amount.

This Debenture is exchangeable, upon the surrender hereof by the Holder at the principal office of the Company, for a new Debenture or Debentures (in accordance with Section 5(d)) representing in the aggregate the outstanding Principal Amount of this Debenture, and each such new Debenture will represent such portion of such outstanding Principal Amount as is designated by the Holder at the time of such surrender.

Whenever the Company is required to issue a new Debenture pursuant to the terms of this Debenture, such new Debenture (i) shall be of like tenor with this Debenture, (ii) shall represent, as indicated on the face of such new Debenture, the Principal Amount remaining outstanding (or in the case of a new Debenture being issued pursuant to Section 5(a) or Section 5(c), the Principal Amount designated by the Holder which, when added to the principal represented by the other new Debentures issued in connection with such issuance, does not exceed the Principal Amount remaining outstanding under this Debenture immediately prior to such issuance of new Debentures), (iii) shall have an issuance date, as indicated on the face of such new Debenture, which is the same as the Issuance Date of this Debenture, and (iv) shall have the same rights and conditions as this Debenture. For the avoidance of doubt, the issuance of a new Debenture shall not release the Company’s obligations with respect to any accrued and unpaid Interest payable on the Principal Amount remaining outstanding.

This Debenture (or any portion hereof) may be assigned or transferred by the Holder to another person only in connection with an assignment or participation by the Holder in its capacity as Lender under and as defined in any of the Loan Agreements and in any event in a Principal Amount corresponding to the percentage of the aggregate Advances under and as defined in the Loan Agreements assigned or participated to such person, in each case as reflected in the Registers under and as defined in the Loan Agreements.

In addition, this Debenture (or any portion hereof) (and any Common Stock that may be issued on conversion of this Debenture as contemplated herein) may be offered, sold, pledged or otherwise transferred only (i) pursuant to an effective registration statement under the Securities Act, or (ii) pursuant to any other exemption from the registration requirements of the Securities Act.

SECTION 6 - MERGER

The Company shall not merge or consolidate with or into or directly or indirectly sell all or substantially all of its properties and assets to any other person unless: (i) the Company is the surviving person; and (ii) immediately after giving effect to the transaction, no Event of Default (or any event which is, or after notice or passage of time or both would be, an Event of Default), shall have occurred and be continuing.

6

SECTION 7 - NOTICES AND OTHER

or at such other address and/or electronic email address and/or to the attention of such other person as the recipient party has specified by written notice given to each other party three (3) Business Days prior to the effectiveness of such change. Written confirmation of receipt (i) given by the recipient of such notice, consent, waiver or other communication, (ii) mechanically or electronically generated by the sender’s computer containing the time, date, recipient’s electronic mail address and the text of such electronic mail or (iii) provided by a nationally recognized overnight delivery service, shall be rebuttable evidence of personal service, receipt by electronic mail or receipt from a nationally recognized overnight delivery service in accordance with clause (i), (ii) or (iii) above, respectively.

7

SECTION 8 - CERTAIN DEFINITIONS

For purposes of this Debenture, the following terms shall have the following meaning:

8

[Signature Page Follows]

9

IN WITNESS WHEREOF, the Company has caused this Convertible Debenture to be duly executed by a duly authorized officer as of the date set forth above.

10

Exhibit 99.2

CERTIFICATE OF DESIGNATION, PREFERENCES AND RIGHTS OF

SERIES I NON-ECONOMIC PREFERRED STOCK

OF

NAVIOS MARITIME HOLDINGS INC.

(Pursuant to Section 35(5) of the

Business Corporations Act of the Associations Law of

the Republic of the Marshall Islands)

The undersigned, Ms. Angeliki Frangou and Ms. Vasiliki Papaefthymiou, do hereby certify:

RESOLVED, that, pursuant to the authority expressly granted to and vested in the Board of Directors (the “Board of Directors”) of Navios Maritime Holdings Inc. (the “Company”) by the provisions of the Amended and Restated Articles of Incorporation (the “Articles of Incorporation”) of the Company and its Bylaws, and in accordance with Section 35(5) of the Business Corporation Act of the Associations Law of the Republic of the Marshall Islands (the “BCA”), there is hereby created, out of the 976,968 shares of preferred stock, par value $0.0001 per share (the “Preferred Stock”), of the Company’s remaining authorized, unissued and undesignated, a series of the Preferred Stock, which series shall have the following powers, designations, preferences and relative, optional or other rights, and the following qualifications, limitations and restrictions (in addition to any powers, designations, preferences and relative, optional or other rights, and any qualifications, limitations and restrictions set forth in the Articles of Incorporation which are applicable to the Preferred Stock):

Section 1. Designation of Amount and Rank.

The shares of such series of Preferred Stock created hereby shall be designated the “Series I Non-Economic Preferred Stock” (the “Series I Non-Economic Preferred Stock”), par value $0.0001 per share. The number of shares of Series I Non-Economic Preferred Stock shall initially be 1,000, which number the Board of Directors may from time to time increase or decrease (but not below the number then-outstanding). The shares of the Series I Non-Economic Preferred Stock are expressly subordinated to the Company’s shares of 8.75% Series G Cumulative Redeemable Perpetual Preferred Stock, 8.625% Series H Cumulative Redeemable Perpetual Preferred Stock and any class or series of capital stock established after the issue date of the Series I Non-Economic Preferred Stock the terms of which class or series expressly provide that it ranks senior to the Series I Non-Economic Preferred Stock, in each case as to dividends and distributions upon any Liquidation Event (as defined below).

Section 2. Liquidation.

The holders of shares of the Series I Non-Economic Preferred Stock shall not be entitled to receive out of the assets of the Corporation or other proceeds legally available for distribution, with respect to such shares, in excess of the par value thereof, in the event of a dissolution, winding up of the affairs or liquidation of the Company, whether voluntary or involuntary (a “Liquidation Event”), and the holders of shares of the Series I Non-Economic Preferred Stock shall only be entitled to receive in respect of such shares the par value thereof in connection with any Liquidation Event if and only if the applicable liquidation preference of all then outstanding shares of Preferred Stock (other than the Series I Non-Economic Preferred Stock) plus the amount of any accumulated and unpaid dividends thereon (whether or not such dividends shall have been declared) shall have been paid to the holders of such outstanding shares of Preferred Stock; provided that holders of shares of the Series I Non-Economic Preferred Stock shall be entitled to receive in

respect of such shares the par value thereof in connection with any Liquidation Event before any payment shall be made or any assets distributed to the holders of any class or series of the common stock, par value $0.0001 per share, of the Company (the “Common Stock”).

Section 3. Dividends.

The holders of the shares of Series I Non-Economic Preferred Stock shall have no entitlements to receive dividends in respect of their shares of Series I Non-Economic Preferred Stock.

Section 4. Voting Rights.

Section 5. Transfer Restrictions.

The shares of Series I Non-Economic Preferred Stock may not be sold, assigned or otherwise transferred except in conjunction with a simultaneous sale of all or a portion of the outstanding principal amount of the Convertible Debenture.

Section 6. Other Rights.

The Series I Non-Economic Preferred Stock shall not have any voting powers, preferences or relative, participating, optional or other special rights, or qualifications, limitations or restrictions thereof, other than as set forth in this Certificate of Designation, the Articles of Incorporation, the Bylaws or as provided by applicable law.

RESOLVED FURTHER, that the President, Chief Executive Officer or any Vice President and the Secretary or any Assistant Secretary of this Company be, and they hereby are, authorized and directed to prepare and file a Certificate of Designation of Rights, Preferences and Privileges in accordance with the foregoing resolution and the provisions of Marshall Islands law and to take such actions as they may deem necessary or appropriate to carry out the intent of the foregoing resolution.

[Remainder of page intentionally left blank. Signature page to follow.]

We further declare under penalty of perjury that the matters set forth in the foregoing Certificate of Designation, Preferences and Rights are true and correct of our own knowledge.

Executed in Piraeus, Greece on January 3^rd, 2022.