Document:

Second Supplemental Agreement, dated January 27, 2011

 Exhibit 4.42 
 Private & Confidential 
 Dated 27 January 2011 

 
  

SECOND SUPPLEMENTAL AGREEMENT 
 relating to a 
 loan of up to US$47,000,000 

to 

IASON OWNING COMPANY LIMITED 
 provided by 
 EFG EUROBANK ERGASIAS S.A. 

 
 

 

 Contents 

 

							
	Clause	  	Page	 
			
	 1
	 	 Definitions
	  	 	1	  
			
	 2
	 	 Consent of the Bank
	  	 	3	  
			
	 3
	 	 Amendments to the Existing Documents
	  	 	3	  
			
	 4
	 	 Representations and warranties
	  	 	5	  
			
	 5
	 	 Conditions
	  	 	6	  
			
	 6
	 	 Supplemental Parties’ confirmation
	  	 	6	  
			
	 7
	 	 Expenses
	  	 	7	  
			
	 8
	 	 Miscellaneous and notices
	  	 	7	  
			
	 9
	 	 Applicable law
	  	 	7	  
		
	 Schedule 1 Documents and evidence required as conditions precedent
	  	 	9	  
		
	 Schedule 2 Form of New Manager’s Undertaking
	  	 	11	  

 THIS SECOND SUPPLEMENTAL AGREEMENT is dated 27 January 2011 and made BETWEEN:

  

	(1)	IASON OWNING COMPANY LIMITED, a corporation incorporated under the laws of the Marshall Islands, whose registered address is at Trust Company Complex, Ajeltake
Road, Ajeltake Island, Majuro, Marshall Islands MH96960 (the “Borrower”); 

  

	(2)	DRYSHIPS INC., a corporation incorporated under the laws of the Marshall Islands, whose registered address is at Trust Company Complex, Ajeltake Road, Ajeltake
Island, Majuro, Marshall Islands MH96960 (the “Corporate Guarantor”); 

  

	(3)	CARDIFF MARINE INC., a corporation incorporated in the Republic of Liberia, whose registered address is at 80 Broad Street, Monrovia, Liberia in its capacity as
manager and in its capacity as corporate guarantor (the “Outgoing Manager”); and 

  

	(4)	EFG EUROBANK ERGASIAS S.A., whose registered office is at 8 Othonos Street, Athens 105 57, Greece acting for the purposes of this Agreement through its office at
83 Akti Miaouli & Flessa Street, Piraeus 185 38, Greece (the “Bank”). 

 WHEREAS:

  

	(A)	this Agreement is supplemental to: 

  

	 	(i)	a loan agreement dated 16 November 2007 as amended by a supplemental agreement dated 15 April 2010 (together, the “Principal Agreement”) made
between the Borrower as borrower and the Bank as lender, pursuant to which the Bank agreed (inter alia) to advance (and has advanced) by way of loan to the Borrower, upon the terms and conditions therein contained, the principal sum of Forty
seven million Dollars ($47,000,000) of which the principal amount outstanding at the date hereof is $23,000,000; and 

  

	 	(ii)	a deed of covenant dated 31 December 2007 as amended by an amendment to it dated 15 April 2010 (together, the “Principal Deed of Covenant”)
collateral to the Mortgage made between the Borrower and the Bank; 

  

	(B)	the Borrower wishes to appoint the New Manager (as defined below) as manager of the Ship in place of the Outgoing Manager; and 

 

	(C)	this Agreement sets out the terms and conditions upon which the Bank shall, at the request of the Borrower, provide its consent to the appointment of the New Manager as
manager of the Ship in place of the Outgoing Manager. 

 NOW IT IS HEREBY AGREED as follows: 

 

	1	Definitions 

  

	1.1	Defined expressions 

Words and expressions defined in the Principal Agreement shall unless the context otherwise requires or unless otherwise defined herein,
have the same meanings when used in this Agreement. 
  

	1.2	Definitions 

 In this
Agreement, unless the context otherwise requires: 
 “Deed of Covenant” means the Principal Deed of Covenant as
amended by this Agreement; 

  
 1 

 “Effective Date” means the date falling no later than 27 January 2011,
on which the Bank notifies the Borrower in writing that it has received the documents and evidence specified in clause 5 and schedule 1 in a form and substance satisfactory to it; 

“Existing Documents” means, together, the Principal Agreement and the Principal Deed of Covenant; 

“Loan Agreement” means the Principal Agreement as amended by this Agreement; 

“New Management Agreement” means the management agreement dated 1 January 2011 made between the New Manager in its
capacity as manager and the Borrower or any other agreement previously approved in writing by the Bank between the Borrower and the New Manager in such capacity, providing (inter alia) for the New Manager to manage the Ship; 

“New Manager” means TMS Bulkers Ltd. of Trust Company Complex, Ajeltake Road, Ajeltake Island, Majuro, Republic of the
Marshall Islands MH96960 and includes its successors in title; 
 “New Manager’s Undertaking” means the
first priority undertaking and assignment in respect of the Ship executed or (as the context may require) to be executed by the New Manager in its capacity as manager in favour of the Bank in the form set out in schedule 2; 

“Relevant Documents” means, together, this Agreement, the New Management Agreement and the New Manager’s
Undertaking, 
 “Relevant Parties” means, together, the Borrower, the Corporate Guarantor, the New Manager and
the Outgoing Manager; and 
 “Supplemental Parties” means the Relevant Parties other than the New Manager.

  

	1.3	Existing Documents 

  

	1.3.1	References in the Principal Agreement to “this Agreement” shall, with effect from the Effective Date and unless the context otherwise requires, be references
to the Principal Agreement as amended by this Agreement and words such as “herein”, “hereof’, “hereunder”, “hereafter”, “hereby” and “hereto”, where they appear in the Principal Agreement,
shall be construed accordingly. 

  

	1.3.2	References in the Principal Deed of Covenant to “this Deed”, shall with effect from the Effective Date and unless the context otherwise requires, be
references to the Principal Deed of Covenant as amended by this Agreement and words such as “herein”, “hereof”, “hereunder”, “hereafter”, “hereby” and “hereto”, where they appear in the
Principal Deed of Covenant, shall be construed accordingly. 

  

	1.4	Headings 

 Clause headings
and the table of contents are inserted for convenience of reference only and shall be ignored in the interpretation of this Agreement. 
  

	1.5	Construction of certain terms 

 In this Agreement, unless the context otherwise requires: 
  

	1.5.1	references to clauses and schedules are to be construed as references to clauses of, and schedules to, this Agreement and references to this Agreement includes its
schedules; 

  

	1.5.2	references to (or to any specified provision of) this Agreement or any other document shall be construed as references to this Agreement, that provision or that
document as in force for the time being and as amended in accordance with terms thereof, or, as the case may be, with the agreement of the relevant parties; 

  
 2 

	1.5.3	references to a “regulation” include any present or future regulation, rule, directive, requirement, request or guideline (whether or not having the
force of law) of any agency, authority, central bank or government department or any self-regulatory or other national or supra-national authority; 

  

	1.5.4	words importing the plural shall include the singular and vice versa; 

  

	1.5.5	references to a time of day are to London time; 

  

	1.5.6	references to a person shall be construed as references to an individual, firm, company, corporation, unincorporated body of persons or any Government Entity;

  

	1.5.7	references to a “guarantee” include references to an indemnity or other assurance against financial loss including, without limitation, an obligation
to purchase assets or services as a consequence of a default by any other person to pay any Indebtedness and “guaranteed” shall be construed accordingly; and 

 

	1.5.8	references to any enactment shall be deemed to include references to such enactment as re- enacted, amended or extended. 

 

	2	Consent of the Bank 

  

	2.1	Consent of Bank 

 The
Bank, relying upon the representations and warranties on the part of the Supplemental Parties contained in clause 4, agrees with the Borrower that, subject to the terms and conditions of this Agreement and in particular, but without prejudice to the
generality of the foregoing, fulfilment on or before 27 January 2011 of the conditions contained in clause 5 and schedule 1, the Bank consents to: 
  

	2.1.1	the substitution of the Outgoing Manager by the New Manager as commercial and technical manager of the Ship; and 

 

	2.1.2	the amendment of the Existing Documents on the terms set out in clause 3. 

  

	2.2	Release of the Outgoing Manager 

 The Bank hereby agrees that, with effect on and from the Effective Date, the Outgoing Manager be (and it is hereby) released from its obligations arising under the Security Documents to which it is a
party. 
  

	3	Amendments to the Existing Documents 

  

	3.1	Amendments to the Principal Agreement 

 The Principal Agreement shall, with effect on and from the Effective Date, be (and it is hereby) amended in accordance with the following provisions (and the Principal Agreement (as so amended) will
continue to be binding upon each of the parties hereto upon such terms as so amended): 
  

	3.1.1	by deleting the definition of “Management Agreement” in clause 1.2 of the Principal Agreement and by inserting in its place the following new
definition of “Management Agreement”: 

 “Management Agreement” means the
agreement dated 1 January 2011 made between the Borrower and the Manager or any other agreement in a form previously approved in writing by the Bank, providing (inter alia) for the Manager to manage the Ship;”; 

 

	3.1.2	by deleting the words “the form set out in schedule 6” in the last line of the definition of “Manager’s Undertaking” in clause 1.2 of
the Principal Agreement and by inserting in their place the words “the form set out in schedule 2 of the Second Supplemental Agreement”; 

  
 3 

	3.1.3	by inserting the following new definition of “Second Supplemental Agreement” in the correct alphabetical order in clause 1.2 of the Principal
Agreement: 

 “Second Supplemental Agreement” means the agreement dated 27 January 2011 made
between (inter alios) the Borrower and the Bank supplemental to this Agreement;”; 
  

	3.1.4	by deleting the definition of “Manager” in clause 1.2 of the Principal Agreement and by inserting in its place the following new definition of
“Manager”: 

 “Manager” means TMS Bulkers Ltd. of Trust Company Complex, Ajeltake
Road, Ajeltake Island, Majuro, Republic of the Marshall Islands MH96960 or any other person appointed by the Borrower, with the prior written consent of the Bank, as the technical and commercial manager of the Ship and, in each such case, includes
its successors in title;”; 
  

	3.1.5	by inserting the words “the Second Supplemental Agreement,” after the words “the First Supplemental Agreement,” in the definition of
“Security Documents” in clause 1.2 of the Principal Agreement; 

  

	3.1.6	by inserting the words “or (in the case of the Manager only) the Second Supplemental Agreement” after the words “of this Agreement” in the third
line of clause 7.1.10 of the Principal Agreement; and 

  

	3.1.7	by inserting the words “or (in the case of the Manager only) from that existing on the date of the Second Supplemental Agreement, each” after the words
“of this Agreement” in the second and third lines of clause 10.1.28 of the Principal Agreement. 

  

	3.2	Amendments to the Principal Deed of Covenant 

 The Principal Deed of Covenant shall, with effect on and from the Effective Date, be (and it is hereby) amended in accordance with the following provisions (and the Principal Deed of Covenant (as so
amended) will continue to be binding upon each of the parties hereto upon such terms as so amended): 
  

	3.2.1	by deleting the definition of “Management Agreement” in clause 1.2 of the Principal Deed of Covenant and by inserting in its place the following new
definition of “Management Agreement”: 

 “Management Agreement” means the
agreement dated 1 January 2011 made between the Owner and the Manager providing for the Manager to manage the Ship or any other agreement previously approved in writing by the Mortgagee between the Owner and the Manager providing (inter
alia) for the Manger to manage the Ship;”; and 
  

	3.2.2	by deleting the definition of “Manager” in clause 1.2 of the Principal Deed of Covenant and by inserting in its place the following new definition of
“Manager”: 

 “Manager” means TMS Bulkers Ltd. of Trust Company Complex, Ajeltake
Road, Ajeltake Island, Majuro, Republic of the Marshall Islands MH96960 or any other person appointed by the Owner, with the prior written consent of the Mortgagee, as the manager of the Ship and includes its successors in title;”. 

 

	3.3	Continued force and effect 

Save as amended by this Agreement, the provisions of each of the Existing Documents and the other Security Documents shall continue in
full force and effect and each of the Existing Documents and this Agreement shall be read and construed as one instrument. 

  
 4 

	4	Representations and warranties 

  

	4.1	Primary representations and warranties 

 Each Supplemental Party represents and warrants to the Bank that: 
  

	4.1.1	Existing representations and warranties 

 the representations and warranties set out in clause 7 of the Principal Agreement and clause 4 of the Corporate Guarantee were true and correct on the date of the Principal Agreement and the Corporate
Guarantee, respectively, and are true and correct, including to the extent that they may have been or shall be amended by this Agreement, as if made at the date of this Agreement with reference to the facts and circumstances existing at such date;

  

	4.1.2	Corporate power 

 each of the
Relevant Parties has power to execute, deliver and perform its obligations under the Relevant Documents to which it is or is to be a party; all necessary corporate, shareholder and other action has been taken by each of the Relevant Parties to
authorise the execution, delivery and performance of the Relevant Documents to which it is or is to be a party; 
  

	4.1.3	Binding obligations 

 the
Relevant Documents to which it is or is to be a party constitute valid and legally binding obligations of each of the Relevant Parties enforceable in accordance with their terms; 

 

	4.1.4	No conflict with other obligations 

 the execution, delivery and performance of the Relevant Documents to which it is or is to be a party by each of the Relevant Parties will not (i) contravene any existing law, statute, rule or
regulation or any judgment, decree or permit to which any of the Relevant Parties is subject, (ii) conflict with, or result in any breach of any of the terms of, or constitute a default under, any agreement or other instrument to which any of
the Relevant Parties is a party or is subject or by which any of the Relevant Parties or any of its property is bound or (iii) contravene or conflict with any provision of the constitutional documents of any of the Relevant Parties (other than
the Personal Guarantor) or (iv) result in the creation or imposition of or oblige any of the Relevant Parties to create any Encumbrance on any of their undertakings, assets, rights or revenues of any of the Relevant Parties; 

 

	4.1.5	No filings required 

 it is not
necessary to ensure the legality, validity, enforceability or admissibility in evidence of any of the Relevant Documents that they or any other instrument be notarised, filed, recorded, registered or enrolled in any court, public office or elsewhere
in any Relevant Jurisdiction or that any stamp, registration or similar tax or charge be paid in any Relevant Jurisdiction on or in relation to the Relevant Documents and each of the Relevant Documents is in proper form for its enforcement in the
courts of the Relevant Jurisdiction; 
  

	4.1.6	Choice of law 

 the choice of
English law to govern the Relevant Documents and the submissions by the Relevant Parties to the non-exclusive jurisdiction of the English courts are valid and binding; and 

 

	4.1.7	Consents obtained 

 every
consent, authorisation, licence or approval of, or registration or declaration to, governmental or public bodies or authorities or courts required by any of the Relevant Parties in connection with the execution, delivery, validity, enforceability or
admissibility in evidence of the Relevant Documents to which it is or is to be a party or the performance by each Relevant Party of its obligations under such document has been obtained or made and is in full force and effect and there has been no
default in the observance of any conditions or restrictions (if any) imposed in, or in connection with, any of the same. 

  
 5 

	4.2	Repetition of representations and warranties 

 Each of the representations and warranties contained in clause 4 1 of this Agreement, clause 7 of the Principal Agreement (as amended by this Agreement) and clause 4 of the Corporate Guarantee shall be
deemed to be repeated by each Supplemental Party on the Effective Date as if made with reference to the facts and circumstances existing on such day. 
  

	5	Conditions 

  

	5.1	Documents and evidence 

The agreements of the Bank referred to in clause 2 shall be subject to the receipt by the Bank of the documents and evidence specified in
schedule 1 in form and substance satisfactory to the Bank. 
  

	5.2	General conditions precedent 

 The agreements of the Bank referred to in clause 2 shall be further subject to: 
  

	5.2.1	the representations and warranties in clause 4 being true and correct on the Effective Date as if each were made with respect to the facts and circumstances existing at
such time; and 

  

	5.2.2	no Default having occurred and continuing at the time of the Effective Date. 

 

	5.3	Waiver of conditions precedent 

 The conditions specified in this clause 5 are inserted solely for the benefit of the Bank and may be waived by the Bank in whole or in part with or without conditions. 

 

	6	Supplemental Parties’ confirmation 

  

	6.1	Security Documents 

 Each
of the Supplemental Parties confirms its agreement to the amendments to the Existing Documents made by this Agreement and the other agreements and arrangements contained in this Agreement (including the release of the Outgoing Manager under clause
2.2), and acknowledges and agrees, for the avoidance of doubt, that: 
  

	6.1.1	each of the Security Documents to which it is a party, and its obligations thereunder, shall remain in full force and effect notwithstanding the amendments made to the
Existing Documents by this Agreement and any other agreements or arrangements contained in this Agreement (including the release of the Outgoing Manager under clause 2.2); 

 

	6.1.2	with effect from the Effective Date, references to “the Agreement” or “the Loan Agreement” in any of the other Security Documents to which it is a
party shall henceforth be references to the Principal Agreement as amended by this Agreement and as from time to time hereafter amended; and 

  

	6.1.3	with effect from the Effective Date, references to “the Deed of Covenant” in any of the Security Documents to which it is a party shall henceforth be
references to the Principal Deed of Covenant as amended by this Agreement and as from time to time hereafter amended. 

  
 6 

	7	Expenses 

  

	7.1	Expenses 

 The Borrower
agrees to pay to the Bank on a full indemnity basis on demand all expenses (including legal and out-of-pocket expenses) incurred by the Bank: 
  

	7.1.1	in connection with the negotiation, preparation, execution and, where relevant, registration of the Relevant Documents and of any amendment or extension of, or the
granting of any waiver or consent under, the Relevant Documents; and 

  

	7.1.2	in contemplation of, or otherwise in connection with, the enforcement of, or preservation of any rights under the Relevant Documents or otherwise in respect of the
monies owing and obligations incurred under the Relevant Documents, 

 together with interest at the rate referred
to in clause 3.4 of the Principal Agreement from the date on which such expenses were incurred to the date of payment (as well after as before judgement). 
  

	7.2	Value Added Tax 

 All
expenses payable pursuant to this clause 7 shall be paid together with value added tax or any similar tax (if any) properly chargeable thereon. 
  

	7.3	Stamp and other duties 

The Borrower agrees to pay to the Bank on demand all stamp, documentary, registration or other like duties or taxes (including any duties
or taxes payable by the Bank) imposed on or in connection with this Agreement and shall indemnify the Bank against any liability arising by reason of any delay or omission by the Borrower to pay such duties or taxes. 

 

	8	Miscellaneous and notices 

  

	8.1	Notices 

 The provisions
of clause 16.1 of the Principal Agreement shall extend and apply to the giving or making of notices or demands hereunder as if the same were expressly stated herein and for this purpose any notices to be sent to the Corporate Guarantor or the
Outgoing Manager shall be sent to the address of the Corporate Guarantor referred to in clause 8.1 of the Corporate Guarantee. 
  

	8.2	Counterparts 

 This
Agreement may be executed in any number of counterparts and by the different parties on separate counterparts, each of which when so executed and delivered shall be an original but all counterparts shall together constitute one and the same
instrument. 
  

	9	Applicable law 

  

	9.1	Law 

 This Agreement and
any non-contractual obligations connected with it are governed by, and shall be construed in accordance with, English law. 
  

	9.2	Submission to jurisdiction 

Each of the Supplemental Parties agrees, for the benefit of the Bank, that any legal action or proceedings arising out of or in connection
with this Agreement (or any non-contractual obligations connected with it) against any of their assets may be brought in the English courts. 

  
 7 

 
Each of the Supplemental Parties irrevocably and unconditionally submits to the jurisdiction of such courts and irrevocably designates, appoints and empowers Ince & Co. at present of
International House, 1 St. Katharine’s Way, London E1W 1AY, England to receive for it and on its behalf, service of process issued out of the English courts in any such legal action or proceedings. The submission to such jurisdiction shall not
(and shall not be construed so as to) limit the right of the Bank to take proceedings against any of the Relevant Parties in the courts of any other competent jurisdiction nor shall the taking of proceedings in any one or more jurisdictions preclude
the taking of proceedings in any other jurisdiction, whether concurrently or not. Each of the Supplemental Parties further agrees that only the courts of England and not those of any other state shall have jurisdiction to determine any claim which
any of the Supplemental Parties may have against the Bank arising out of or in connection with this Agreement (or any non-contractual obligations connected with it). 
  

	9.3	Contracts (Rights of Third Parties) Act 1999 

 No term of this Agreement is enforceable under the Contracts (Rights of Third Parties) Act 1999 by a person who is not a party to this Agreement. 

IN WITNESS whereof the parties to this Agreement have caused this Agreement to be duly executed as a deed on the date first above
written. 

  
 8 

 Schedule 1 
 Documents and evidence required as conditions precedent 
 (referred to in
clause 5.1) 
  

	1	Corporate authorisations 

In relation to each of the Relevant Parties: 
  

	 	(a)	Constitutional documents 

copies certified by an officer of each of the Relevant Parties, as a true, complete and up to date copies, of all documents which contain
or establish or relate to the constitution of that party or a secretary’s certificate confirming that there have been no changes or amendments to the constitutional documents certified copies of which were previously delivered to the Bank
pursuant to the Principal Agreement; 
  

	 	(b)	Resolutions 

 copies of
resolutions of each of its board of directors and its shareholders approving this Agreement and the other Relevant Documents and the terms and conditions hereof and thereof and authorising the signature, delivery and performance of each such
party’s obligations thereunder, certified by an officer of such Relevant Party as: 
  

	 	(1)	being true and correct; 

  

	 	(2)	being duly passed at meetings of the directors of such Relevant Party and, as the case may be, of the shareholders of such Relevant Party each duly convened and held;

  

	 	(3)	not having been amended, modified or revoked; and 

  

	 	(4)	being in full force and effect, 

together with originals or certified copies of any powers of attorney issued by any party pursuant to such resolutions; and 

 

	 	(c)	Certificate of incumbency 

a list of directors and officers of each Relevant Party specifying the names and positions of such persons, certified by an officer of
such Relevant Party to be true, complete and up to date; 
  

	2	Consents 

 a certificate
from an officer of each of the Relevant Parties stating that no consents, authorisations, licences or approvals are necessary for such Relevant Party to authorise, or are required by each of the Relevant Parties or any other party (other than the
Bank) in connection with, the execution, delivery, and performance of this Agreement and the other Relevant Documents to which such Relevant Party is or is to be a party; 

 

	3	Relevant Documents 

 the
New Manager’s Undertaking and any notices of assignment required thereunder and in the form prescribed by the New Manager’s Undertaking, each duly executed by the New Manager; 

  
 9 

	4	New Management Agreement 

a certified copy of the New Management Agreement; 
  

	5	Ownership 

 evidence,
satisfactory in all respects to the Bank, that all shares in the New Manager are legally and/or beneficially owned and held by persons acceptable to the Bank in its sole discretion; 

 

	6	Insurance 

 evidence that
the insurers of the Ship have been notified of and have approved the change in management in respect of the Ship and that the new notices of assignment executed by the New Manager under the New Manager’s Undertaking, have been endorsed by such
insurers on the relevant policies; 
  

	7	DOC/SMC 

 a certified true
and complete copy by an officer of the Borrower of the DOC issued to the New Manager in its capacity as manager and a copy of the SMC of the Ship; 
  

	8	Legal opinions 

 such
legal opinions in relation to the laws of the Republic of the Marshall Islands and the laws of the Republic of Liberia and any other legal opinions as the Bank shall in its absolute discretion require; and 

 

	9	Process agent 

 a letter
from each Relevant Party’s agent for receipt of service of proceedings accepting its appointment under this Agreement and the other Relevant Documents to which such Relevant Party is or is to be a party as such Relevant Party’s process
agent. 

  
 10 

 Schedule 2 
 Form of New Manager’s Undertaking 

  
 11 

 Private & Confidential 
 Manager’s Undertaking 
  

	To:	EFG Eurobank Ergasias S.A. 

 83
Akti Miaouli & Flessa Street 
 185 38 Piraeus 
 Greece 
  

	From:	TMS Bulkers Ltd. 

 Trust Company
Complex 
 Ajeltake Road 
 Ajeltake Island 
 Majuro 

MH96960 Marshall Islands 
 Date: 27 January 2011 
 Dear Sirs 
 US$47,000,000 loan agreement relating to a Loan to lason Owning Company Limited as amended and supplemented by a first supplemental agreement dated 15 April 2010 and as further amended and
supplemented by a second supplemental agreement dated 27 January 2011 
  

	1	Loan Agreement 

  

	1.1	We understand that under a loan agreement dated 16 November 2007 (the “Principal Agreement”) made between (1) EFG Eurobank Ergasias S.A. (the
“Bank”) as lender and (2) lason Owning Company Limited (the “Owner”) as borrower, as amended and supplemented by a first supplemental agreement dated 15 April 2010 (the “First Supplemental
Agreement”) and as further amended and supplemented by a second supplemental agreement dated 27 January 2011 (the “Second Supplemental Agreement” and, together with the Principal Agreement and the First Supplemental
Agreement, the “Loan Agreement”), each made between (inter alios) the Owner and the Bank, the Bank has agreed to make available (and has made available) to the Owner a loan of up to $47,000,000 and that it is a condition precedent
to the Bank granting its consent to certain matters contained in the Second Supplemental Agreement that we, TMS Bulkers Ltd. (the “Manager”), execute this letter of undertaking (the “Letter”) in favour of the Bank.

  

	1.2	We also understand that under a 1992 ISDA master agreement dated as of 16 November 2007 (the “Master Swap Agreement”) and made between the Owner
and the Bank, the Bank agreed the terms and conditions upon which it would enter into interest rate swap or other derivative transactions with the Owner, whether in respect of the Loan (whether in whole or part as the case may be from time to time)
or for any other purpose whatsoever. 

  

	1.3	Words and expressions defined in the Loan Agreement shall, unless otherwise specified herein, have the same meanings when used herein. 

 

	2	Confirmation of appointment 

 We hereby confirm that we have been appointed as the manager of m.v. Oregon (the “Ship”) registered under the flag of the Republic of Malta in the name of the Owner pursuant to a
management agreement dated 1 January 2011 (the “Management Agreement”) made between ourselves and the Owner and that we have accepted our appointment thereunder in accordance with the terms and conditions thereof. 

  
 1 

	3	Representations and warranties 

  

	3.1	We hereby represent and warrant that the copy of the Management Agreement set out in Appendix 1 to this Letter is a true and complete copy of the Management Agreement,
that the Management Agreement constitutes valid and binding obligations of the Manager enforceable in accordance with its terms and that there have been no amendments or variations thereto or defaults thereunder by the Manager or, to the best of the
Manager’s knowledge and belief, by the Owner. 

  

	3.2	We hereby confirm that the representations and warranties set out in clauses 7.2,9, 7.2.10 and 7.2.11 of the Loan Agreement are true and correct in all respects.

  

	4	Undertakings 

 The Manager
undertakes with the Bank that throughout the Security Period (as such term is defined in the deed of covenant dated 31 December 2007 as amended by an amendment to it dated 15 April 2010 (together the “Deed of Covenant”)
executed by the Owner in favour of the Bank): 
  

	4.1	the Manager will not agree or purport to agree to any amendment or variation of the Management Agreement without the prior written consent of the Bank;

  

	4.2	the Manager will procure that any sub-manager appointed by the Manager pursuant to the provisions of the Management Agreement or otherwise will, on or before the date
of such appointment enter into an undertaking in favour of the Bank in substantially the same form (mutatis mutandis) as this Letter; 

  

	4.3	the Manager will not, without the prior written consent of the Bank, take any action or institute any proceedings or make or assert any claim on or in respect of the
Ship or its policies and contracts of insurance (which expression includes all entries of the Ship in a protection and indemnity or war risks association) which are from time to time during the Security Period (as defined in the Deed of Covenant) in
place or taken out or entered into by or for the benefit of the Owner (whether in the sole name of the Owner or in the joint names of the Owner and the Bank or otherwise) in respect of the Ship and her Earnings (as such term is defined below) or
otherwise howsoever in connection with the Ship and all benefits thereof (including claims of whatsoever nature and return of premiums) (the “Insurances”) or any moneys whatsoever from time to time due or payable to the Owner during
the Security Period arising out of the use or operation of the Ship including (but without limiting the generality of the foregoing) all freight, hire and passage moneys, income arising under pooling arrangements, compensation payable to the Owner
in event of requisition of the Ship for hire, remuneration for salvage and towage services, demurrage and detention moneys and damages for breach (or payments for variation or termination) of any charterparty or other contract for the employment of
the Ship (the “Earnings”) or any other property or other assets of the Owner which the Bank has previously advised the Manager are subject to any Encumbrance or right of set-off in favour of the Bank by virtue of any of the Security
Documents or otherwise; 

  

	4.4	the Manager will discontinue any such action or proceedings or claim which may have been taken, instituted or made or asserted, promptly upon notice from the Bank to do
so; 

  

	4.5	the Manager does hereby subordinate any claim that it may have against the Owner or otherwise in respect of the Ship and its Earnings, Insurances and Requisition
Compensation (as such term is defined in the Deed of Covenant) to the claims of the Bank under the Loan Agreement, the Master Swap Agreement and the other Security Documents and undertakes not to exercise any right to which it may be entitled in
respect of the Owner and/or the Ship and/or its Earnings and/or Insurances and/or Requisition Compensation in competition with the Bank; 

  
 2 

	4.6	the Manager will promptly notify the Bank if at any time the amount owed by the Owner to the Manager pursuant to the Management Agreement (whether in respect of the
Manager’s remuneration or disbursements or otherwise) exceeds One hundred thousand Dollars ($100,000) or the equivalent in other currencies; and 

  

	4.7	the Manager will provide the Bank with such information concerning the Ship as the Bank may from time to time reasonably require. 

 

	5	Insurance assignment 

  

	5.1	By way of security for the repayment of the aggregate of the Loan, the Master Swap Agreement Liabilities (as defined in the Deed of Covenant) and interest accrued and
accruing thereon, the Expenses (as such term is defined in the Deed of Covenant) and all other sums of money from time to time owing by the Owner to the Bank, whether actually or contingently, under the Loan Agreement, the Master Swap Agreement and
the other Security Documents or any of them to which the Owner is or is to be a party (the “Outstanding Indebtedness”), the Manager with full title guarantee hereby irrevocably and unconditionally assigns and agrees to assign to the
Bank all of the Manager’s rights, title and interest in and to all the benefit of the Insurances. 

  

	5.2	The Manager hereby undertakes to procure that a duly completed notice in the form set out in Appendix 2 to this Letter is given to all insurers of the Ship and to
procure that such notice is promptly endorsed on all policies and entries in respect of the Insurances and agrees promptly to authorise and/or instruct any broker, insurer or association with or through whom Insurances may be effected to endorse on
any policy or entry or otherwise to give effect to such loss payable clause as may be stipulated by the Bank. 

  

	5.3	The Bank shall, at the Manager’s cost and request, re-assign to the Manager all the Manager’s right, title and interest in the Insurances upon the Outstanding
Indebtedness being paid and discharged in full to the satisfaction of the Bank. 

  

	5.4	Any moneys in respect of the Insurances which would (but for the assignment contained in clause 5.1 above) be payable to the Manager shall be applied in accordance with
clause 8.1 and/or clause 8.4 of the Deed of Covenant. 

  

	6	Acknowledgement 

 The
Manager hereby acknowledges that it has seen and has reviewed the Loan Agreement, the Master Swap Agreement and the other Security Documents and agrees to abide by and to observe the provisions thereof insofar as the same are applicable to it as
therein provided. 
  

	7	Law and jurisdiction 

  

	7.1	The agreement constituted by this Letter and any non-contractual obligations in connection with this Letter are governed by, and shall be construed in accordance with,
English law. 

  

	7.2	The Manager agrees, for the benefit of the Bank, that any legal action or proceedings arising out of or in connection with this Letter (including any non-contractual
obligations connected with this Letter) against the Manager or any of its assets may be brought in the English courts. The Manager irrevocably and unconditionally submits to the jurisdiction of such courts and irrevocably designates, appoints and
empowers Ince & Co. at present of International House, 1 St. Katharine’s Way, London E1W 1AY, England to receive for it and on its behalf, service of process issued out of the English courts in any such legal action or proceedings. The
submission to such jurisdiction shall not (and shall not be construed so as to) limit the rights of the Bank to take any proceedings against the Manager in the courts of any other competent jurisdiction nor shall the taking of proceedings in any one
or more jurisdictions preclude the taking of proceedings in any other jurisdiction, whether concurrently or not. 

  
 3 

	7.3	No term of this Letter is enforceable under the provisions of the Contracts (Rights of Third Parties) Act 1999 by a person who is not a party to this Letter or to whom
this Letter is not addressed. 

 Yours faithfully, 

 

	
	  

	For and on behalf of
	TMS BULKERS LTD.

  
 4 

 Appendix 1 
 Copy of the Management Agreement 

  
 5 

 Appendix 2 
 Notice of Assignment 
 We, TMS BULKERS LTD., the managers of the motor vessel
Oregon HEREBY GIVE NOTICE that by a first assignment dated [—] and entered into by us with EFG EUROBANK ERGASIAS S.A. there has been assigned by us to the said EFG EUROBANK ERGASIAS
S.A. as first assignees all of our right, title and interest in and to the insurances in respect of the said Ship including the insurances constituted by the Policy whereon this notice is endorsed. 

 

	
	  

	SIGNED
	for and on behalf of
	TMS BULKERS LTD.
	
	Dated: [—]

  
 6 

									
	EXECUTED as a DEED	 	)	  		  	
	by E. PAPAPONTIKOU	 	)	  		  	
	for and on behalf of	 	)	  		  	 /s/ E. PAPAPONTIKOU

	IASON OWING COMPANY LIMITED	 	)	  		  	Attorney-in-fact
	as Borrower	 	)	  		  	
	in the presence of:	 	)	  		  	
				
	 /s/ Pinelopi - Anna Miliou
	 		  		  	
	Witness	 		 		  		  	
	Name:	 	Pinelopi - Anna Miliou	 		  		  	
	Address:	 	Norton Rose LLP, Athens	 		  		  	
	Occupation:	 	Solicitor	 		  		  	
				
	EXECUTED as a DEED	 	)	  		  	
	by E. PAPAPONTIKOU	 	)	  		  	
	for and on behalf of	 	)	  		  	 /s/ E. PAPAPONTIKOU

	DRYSHIPS INC.	 	)	  		  	Attorney-in-fact
	as Corporate Guarantor	 	)	  		  	
	in the presence of:	 	)	  		  	
				
	 /s/ Pinelopi - Anna Miliou
	 		  		  	
	Witness	 		 		  		  	
	Name:	 	Pinelopi - Anna Miliou	 		  		  	
	Address:	 	Norton Rose LLP, Athens	 		  		  	
	Occupation:	 	Solicitor	 		  		  	
				
	EXECUTED as a DEED	 	)	  		  	
	by E. PAPAPONTIKOU	 	)	  		  	
	for and on behalf of	 	)	  		  	 /s/ E. PAPAPONTIKOU

	CARDIFF MARINE INC.	 	)	  		  	Attorney-in-fact
	as Outgoing Manager	 	)	  		  	
	in the presence of:	 	)	  		  	
				
	 /s/ Pinelopi - Anna Miliou
	 		  		  	
	Witness	 		 		  		  	
	Name:	 	Pinelopi - Anna Miliou	 		  		  	
	Address:	 	Norton Rose LLP, Athens	 		  		  	
	Occupation:	 	Solicitor	 		  		  	
					
	SIGNED by	 	M. TZOUTZOURAKI	 	)	  		  	 /s/ M. TZOUTZOURAKI

	and by S. HYDREOU	 	)	  		  	Authorised Signatory
	for and on behalf of	 	)	  		  	
	EFG EUROBANK ERGASIAS S.A.	 	)	  		  	 /s/ S. HYDREOU

	as Bank	 	)	  		  	Authorised Signatory

  
 12Supplemental Letter, dated September 23, 2011

 Exhibit 4.46 
  

 
  

	To:	Team-Up Owning Company Limited 

 Trust Company Complex 
 Ajeltake Road 

Ajeltake Island 

Majuro 
 Marshall
Islands MH96960 
 Orpheus Owning Company Limited 

Trust Company Complex 
 Ajeltake Road 
 Ajeltake Island 

Majuro 
 Marshall
Islands MH96960 
 DryShips Inc. 
 Trust Company Complex 
 Ajeltake Road 

Ajeltake Island 

Majuro 
 Marshall
Islands MH96960 
 TMS Bulkers Ltd. 
 Trust Company Complex 
 Ajeltake Road 

Ajeltake Island 

Majuro 
 Marshall
Islands MH96960 
 23rd September 2011 
 Dear Sirs 
 US$101,150,000 loan facility to Team-Up Owning Company Limited and Orpheus Owning
Company Limited as amended and supplemented 
  

	1	We refer to the loan agreement dated 4 December 2007 (the “Principal Agreement”) made between (1) Team-Up Owning Company Limited and Orpheus
Owning Company Limited as joint and several borrowers (therein and herein together referred to as the “Borrowers”), (2) DnB NOR Bank ASA as arranger (in such capacity the “Arranger”), agent (in such capacity
the “Agent”), security agent (in such capacity the “Security Agent”), swap provider and account bank and (3) the banks and financial institutions referred to in schedule 1 thereto as lenders (the
“Banks”), as amended and supplemented by a first supplemental agreement dated 11 June 2009 (the “First Supplemental Agreement”) and as further amended and supplemented by a second supplemental agreement dated
26 January 2011 (the “Second Supplemental Agreement” and, together with the Principal Agreement and the First Supplemental Agreement, the “Loan Agreement”), whereby the Banks agreed (inter alia) to advance (and
have advanced) by way of loan to the Borrowers, upon the terms and conditions therein contained, the principal sum of up to One hundred and one million one hundred and fifty thousand Dollars ($101,150,000). 

 

	2	We also refer to the corporate guarantee dated 4 December 2007 (the “Corporate Guarantee”) made between (1) DryShips Inc. as corporate
guarantor (the “Guarantor”) and (2) the Security Agent. 

  

	3	Words and expressions defined in the Loan Agreement and the Corporate Guarantee shall, unless the context otherwise requires or unless otherwise defined herein, have
the same meanings when used in this letter. 

 Dnb NOR Bank ASA 20 St. Durban’s Hill, London EC3R 8HY  Tel: 020
7621 1111  Fax: 020 7626 7400   www.dnbnor.no 
 DnB NOR Bank ASA Incorporated in Norway with Limited
Liability.  Registration No: 984851006.  Head Office: 0021 Oslo, Norway. 
 DnB NOR Bank ASA London Branch Registration in
UK FC025119 
 Authorised by Finanstilsynet and subject to limited regulation by the Financial Services Authority. Details on the extent of our
regulation by the Financial Services Authority are available on request. 

 

 
  

	4	Following the relevant request of the Borrowers and the Guarantor and subject to receipt by the Agent of the fee (referred to in paragraph 5 below), we confirm that the
Creditors hereby agree to waive the application of clause 5.3.1(c) of the Corporate Guarantee for any Accounting Periods ending within the period between 30 September 2011 and 31 December 2012 (both inclusive) Provided however that,
for the avoidance of doubt, such waiver shall not prejudice the Security Agent’s and/or the Agent’s and/or any Banks’ right to demand compliance by the Guarantor, and the Guarantor’s obligation to comply, with such clause in
relation to any financial period beginning on or after 1 January 2013. 

  

	5	The agreement of the Creditors in paragraph 4 above shall not take effect unless and until: 

 

	 	(a)	The Borrowers, the Guarantor and the Manager have executed by their duly authorised representatives this letter, and have returned it to the Agent as so executed; and

  

	 	(b)	the Borrowers have paid to the Agent for its own account, on or prior to the date of this letter, a waiver fee of USD 5,000 (Five thousand U.S Dollars).

  

	6	This letter and any non contractual obligations in connection with this letter are governed by, and shall be construed in accordance with, English law.

  

					
	 /s/ Illegible
	 	 /s/ Illegible
	  	

	
	Signed by:
	for and on behalf of
	DNB NOR BANK ASA
	as Arranger, Agent, Security Agent, Bank, Swap Provider and Account Bank

 We, TEAM-UP OWNING COMPANY LIMITED, hereby acknowledge and agree to the above and confirm that the Security
Documents (as such term is defined in the Loan Agreement) executed by us will remain valid and effective notwithstanding any amendments made to the Loan Agreement by the terms of this letter. 

 

	
	 /s/ EUGENIA PAPAPONTIKOU

	Signed by: Eugenia Papapontikou
	for and on behalf of
	TEAM-UP OWNING COMPANY LIMITED
	
	Dated: 23rd September 2011

 We, ORPHEUS OWNING COMPANY LIMITED, hereby acknowledge and agree to the above and confirm that the Security
Documents (as such term is defined in the Loan Agreement) executed by us will remain valid and effective notwithstanding any amendments made to the Loan Agreement by the terms of this letter. 

 

	
	 /s/ EUGENIA PAPAPONTIKOU

	Signed by: Eugenia Papapontikou
	for and on behalf of
	ORPHEUS OWNING COMPANY LIMITED
	
	Dated: 23rd September 2011

 DnB NOR Bank ASA 20 St. Dunstan’s Hill, London EC3R 8HY  Tel: 020 7621 1111  Fax: 020 7626
7400  www.dnbnor.no 
 DnB NOR Bank ASA Incorporated in Norway with Limited Liability.  Registration No:
984851006.  Head Office: 0021 Oslo, Norway. 
 DnB NOR Bank ASA London Branch Registration in UK FC025119 

Authorised by Finanstilsynet and subject to limited regulation by the Financial Services Authority. Details on the extent of our regulation by the
Financial Services Authority are available on request. 

  
 2 

 

 
 We, DRYSHIPS INC., hereby acknowledge and agree to the above and confirm that the Security Documents (as such
term is defined in the Loan Agreement) executed by us will remain valid and effective notwithstanding any amendments made to the Loan Agreement by the terms of this letter. 

 

	
	 /s/ EUGENIA PAPAPONTIKOU

	Signed by: Eugenia Papapontikou
	for and on behalf of
	DRYSHIPS INC.
	
	Dated: 23rd September 2011

 We, TMS BULKERS LTD., hereby acknowledge and agree to the above and confirm that the Manager’s Undertakings
(as such term is defined in the Loan Agreement) executed by us will remain valid and effective notwithstanding any amendments made to the Loan Agreement by the terms of this letter. 

 

	
	 /s/ EUGENIA PAPAPONTIKOU

	Signed by: Eugenia Papapontikou
	for and on behalf of
	TMS BULKERS LTD.
	
	Dated: 23rd September 2011

 DnB NOR Bank ASA 20 St. Dunstan’s Hill, London EC3R 8HY  Tel: 020 7621 1111  Fax: 020 7626
7400  www.dnbnor.no 
 DnB NOR Bank ASA Incorporated in Norway with Limited Liability.  Registration No:
984851006.  Head Office: 0021 Oslo, Norway. 
 DnB NOR Bank ASA London Branch Registration in UK FC025119 

Authorised by Finanstilsynet and subject to limited regulation by the Financial Services Authority. Details on the extent of our regulation by the
Financial Services Authority are available on request. 

  
 3

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