Document:

First Supplemental Agreement, dated February 25, 2010

 Exhibit 4.44 
 DATED 25 FEBRUARY 2010 
 IONIAN TRADERS INC,

 NORWALK STAR OWNERS INC. 
 (as Borrowers) 
 -and- 
 DRYSHIPS INC. 
 (as Guarantor) 
 -and- 
 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT 
 UNICREDIT BANK AG

 (as Lenders) 
 -and- 
 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT 
 (as agent) 
 -and- 
 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT 
 UNICREDIT BANK AG 
 (as Swap Providers)

 -and- 
 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT 
 (as Security Agent)

  
  
 FIRST SUPPLEMENTAL AGREEMENT TO SECURED 
 LOAN FACILITY AGREEMENT DATED 13 MAY 2008 
  
  
 STEPHENSON
HARWOOD 
 Piraeus Office 
 Ariston Building 
 2 Filellinon Street and Akti Miaouli 
 Piraeus 185 36, Greece 
 Tel:+30 210 4295 160 
 Fax: +30 210 4295 166 
 Ref: F09.242 

 CONTENTS 
  

			
	 	  	Page
		
	 1       Interpretation
	  	2
		
	 2       Conditions
	  	4
		
	 3       Representations and Warranties
	  	6
		
	 4       Amendments to Loan Agreement
	  	6
		
	 5       Confirmation and Undertaking
	  	18
		
	 6       Communications, Law and Jurisdiction
	  	18
		
	 Schedule 1 The Lenders, the Commitments and the Swap Providers
	  	19
		
	 Schedule 2 Effective Date Confirmation
	  	20

 SUPPLEMENTAL AGREEMENT 
 Dated: 25 February 2010 
 BETWEEN: 
  

	(1)	NORWALK STAR OWNERS INC. (“Norwalk”), and IONIAN TRADERS INC. (“Ionian”), both companies incorporated under the laws of
the Republic of the Marshall Islands whose registered office is at Trust Company Complex, Ajeltake Road, Ajeltake Island, Majuro, Marshall Islands MH 96960, (together the “Borrowers” and each a “Borrower”) jointly
and severally; and 

  

	(2)	DRYSHIPS INC., a company incorporated according to the law of the Marshall Islands whose registered office is at Trust Company Complex, Ajeltake Road, Ajeltake
Island, Majuro, Marshall Islands MH 96960; and 

  

	(4)	DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT, acting as lender through its office at 17, Domshof, 28195, Bremen, Federal Republic of Germany and UNICREDIT BANK
AG (formerly known as Bayerische Hypo- und Vereinsbank AG), of Kardinal-Faulhaber-Strasse 1, 8033 Munich, acting as lender through its office at Alter Wall 22, D-20457 Hamburg, Federal Republic of Germany (together the “Lenders”
and each a “Lender”); and 

  

	(5)	DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT, acting as agent through its office at 17, Domshof, 28195, Bremen, Federal Republic of Germany (in that capacity the
“Agent”); and 

  

	(6)	DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT, acting as swap provider through its office at 17, Domshof, 28195, Bremen, Federal Republic of Germany and UNICREDIT BANK
AG (formerly known as Bayerische Hypo- und Vereinsbank AG), of Kardinal-Faulhaber-Strasse 1, 8033 Munich, acting as swap provider through its office at Alter Wall 22, D-20457 Hamburg, Federal Republic of Germany (together, the “Swap
Provider” and each a “Swap Provider”); and 

  

	(7)	DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT, acting as security agent through its office at 17, Domshof, 28195, Bremen, Federal Republic of Germany (in that capacity
the “Security Agent”). 

 SUPPLEMENTAL TO a secured loan agreement dated 13 May 2008 (the “Loan
Agreement”) made between the Borrower, the Lenders, the Agent, the Swap Providers and the Security Agent on the terms and subject to the conditions of which each of the Lenders has agreed to advance to the Borrowers on a joint and several
basis its Commitment (aggregating, with all the other Commitments, an amount not exceeding the lesser of (i) $125,000,000 and (ii) sixty per cent (60%) of the Fair Market Value on the Drawdown Date) to assist the Borrowers to finance
part of the aggregate Purchase Price of the Vessels (the “Loan”). 
 WHEREAS: 
  

	(A)	(i) The Guarantor is currently in breach of the financial covenants as set out in clause 6.6 of the Guarantee and (ii) the Borrowers are currently in breach of
clauses 10.4 (Additional security) and 12.2 of the Loan Agreement. 

  

	(B)	The Borrowers and the Guarantor have requested that the Lenders agree to amend the requirements in clauses 10.4 (Additional security) and 12.2 of the Loan
Agreement clause 6.6 of the Guarantee during the Waiver Period. 

  

	(C)	The Lenders are willing to agree to all the foregoing subject to the terms and conditions set forth in this Supplemental Agreement, including, but not limited to, the
amendments to be made to the Loan Agreement and the Guarantee in accordance with the terms and conditions contained herein. 

 IT IS AGREED THAT: 
  

	1	Interpretation 

  

	 	1.1	In this Supplemental Agreement:- 

 “Additional Security Documents” means the Account Pledge, the Mortgage Amendments and this Supplemental Agreement. 
 “Account Pledge” means the account pledge to be granted by each Borrower in favour of the Security Agent in respect of each Earnings Account. 
 “Charter” means:- 
  

	 	(i)	in respect of “POSITANO” the time charterparty dated 3 September 2008 made between Ionian, as owner and a Charterer, as charterer (as same may be
supplemented, novated and/or replaced from time to time); and 

  

 2 

	 	(ii)	in respect of “CAPRI” the time charterparty dated 6 May 2008 made between Norwalk, as owner and a Charterer, as charterer (as same may be supplemented,
novated and/or replaced from time to time), 

 or any other charter or contract of employment in relation to a
Vessel in each case, in form and substance acceptable to the Lenders and “Charters” means both of them. 
 “Charterer” means a charterer who may enter into a Charter in respect of a Vessel and “Charterers” means both of them. 
 “Earnings Accounts” means the bank accounts opened in the names of the Borrowers with the Agent and designated respectively “Ionian Traders Inc.—Earnings Account” and
“Norwalk Star Owners Inc.—Earnings Account” and each an “Earnings Account”. 
 “Effective Date” means the date on which the Agent confirms to the Borrower in writing substantially in the form set out in Schedule 2 that all of the conditions referred to in Clause 2.1 have been satisfied, which
confirmation the Agent shall be under no obligation to give if an Event of Default shall have occurred. 
 “Finance
Parties” means the Agent, the Security Agent, the Swap Providers and the Lenders. 
 “Mortgage Amendments”
means the amendments to the Mortgages in favour of the Security Agent in such form and containing such terms and conditions as the Security Agent shall require, and “Mortgage Amendment” means any one of them. 
 “Security Parties” means all parties to this Supplemental Agreement other than the Finance Parties. 
 “Waiver Period” means the period commencing on 1 January 2009 and expiring at midnight 31 December 2010.

  

 3 

	 	1.2	All words and expressions defined in the Loan Agreement shall have the same meaning when used in this Supplemental Agreement unless the context otherwise requires, and
clause 1.2 of the Loan Agreement shall apply to the interpretation of this Supplemental Agreement as if it were set out in full. 

  

	 	1.3	All obligations, representations, warranties, covenants and undertakings of the Borrowers under or pursuant to this Supplemental Agreement shall, unless otherwise
expressly provided, be entered into, made or given by them jointly and severally. 

  

	2	Conditions 

  

	 	2.1	As conditions for the agreement of the Finance Parties to the requests specified in Recital (B) above and for the effectiveness of Clause 4, the Borrower shall
deliver or cause to be delivered to or to the order of the Agent the following documents and evidence: 

  

	 	2.1.1	a certificate from a duly authorised officer of each of the Security Parties confirming that none of the documents delivered to the Agent pursuant to Schedule 2, Part
I, 1 (a), (c), (d), (g) of the Loan Agreement have been amended or modified in any way since the date of their delivery to the Agent, or copies, certified by a duly authorised officer of the Security Party in question as true, complete,
accurate and neither amended nor revoked, of any which have been amended or modified; 

  

	 	2.1.2	a copy, certified by a director or the secretary of the Security Party in question as true, complete and accurate and neither amended nor revoked, of a resolution of
the directors of each Security Party and a resolution of the shareholders of each Borrower (together, where appropriate, with signed waivers of notice of any directors’ or shareholders’ meetings) approving, and authorising or ratifying the
execution of, this Supplemental Agreement and any document to be executed by that Security Party pursuant to this Supplemental Agreement; 

  

	 	2.1.3	a notarially attested and legalised power of attorney of each of the Security Parties under which this Supplemental Agreement and any documents required pursuant to it
are to be executed by that Security Party; 

  

 4 

	 	2.1.4	a certificate of goodstanding in respect of each Security Party; 

  

	 	2.1.5	the Additional Security Documents, duly executed and, in the case of the Amendment Mortgage, registered against the Vessel with first priority, together with all other
documents required by any of them, including, without limitation, all notices of assignment and/or charge and evidence that those notices will be duly acknowledged by the recipients. 

  

	 	2.1.6	a legal opinion, in draft form, of the legal advisers to the Lenders in each relevant jurisdiction, substantially in the form or forms provided to the Agent prior to
signing this Agreement or confirmation satisfactory to the Agent that such an opinion will be given; 

  

	 	2.1.7	the Charters; 

  

	 	2.1.8	evidence of payment to the Agent (for the account of the Lenders) of an amendment fee of one hundred and twenty five thousand Dollars ($125,000); and

  

	 	2.1.9	evidence of payment to the Agent (for the account of the Lenders) of the difference between the interest payable calculated on the basis of the Margin applicable during
the Waiver Period (being 1.9% per annum) and the interest actually paid and calculated on the basis of the Margin applicable during all other times during the Facility Period (being 1.15% per annum) for the period commencing on
1 January 2009 and ending on the Effective Date. 

  

	 	2.2	All documents and evidence delivered to the Agent pursuant to this Clause shall: 

  

	 	2.2.1	be in form and substance acceptable to the Agent; 

  

	 	2.2.2	be accompanied, if required by the Agent, by translations into the English language, certified in a manner acceptable to the Agent; and 

  

	 	2.2.3	if required by the Agent, be certified, notarised, legalised or attested in a manner acceptable to the Agent. 

  

 5 

	3	Representations and Warranties 

 Each of the representations and warranties contained in clause 11 of the Loan Agreement shall be deemed repeated by the Borrower at the date of this Supplemental Agreement and at the Effective Date, by reference to the facts and
circumstances then pertaining, as if references to the Finance Documents included this Supplemental Agreement. 
  

	4	Amendments to Loan Agreement and the Guarantee 

 With effect from the Effective Date: 
  

	 	4.1	the following additional definitions shall be added in clause 1.1 of the Original Loan Agreement, and the alphabetical and numerical order of the remaining definitions
in such clause shall be amended accordingly:- 

 “Additional Security Documents” means the
Account Pledge, the Mortgage Amendments and this Supplemental Agreement. 
 “Account Pledge” means the account
pledge to be granted by each Borrower in favour of the Security Agent in respect of each Earnings Account. 
 “Cash” means cash in hand which is not subject to any charge back or other Encumbrance and to which the Guarantor has free, immediate and direct access. 
 “Charter” means:- 
  

	 	(i)	in respect of “POSITANO” the time charterparty dated 3 September 2008 made between Ionian, as owner and a Charterer, as charterer (as same may be
supplemented, novated and/or replaced from time to time); and 

  

	 	(ii)	in respect of “CAPRI” the time charterparty dated 6 May 2008 made between Norwalk, as owner and a Charterer, as charterer (as same may be supplemented,
novated and/or replaced from time to time), 

 or any other charter or contract of employment in relation to a
Vessel in each case, in form and substance acceptable to the Lenders, 
 “Charterers” means the charterers who
may enter into a Charter in respect of a Vessel and “Charterer” means any one of them. 
  

 6 

 “Debt Service” means the aggregate (as of the date of calculation) of all
obligations of a member of the Group then outstanding for the payment or repayment of principal plus interest thereon plus bareboat charter obligations owed by a member of the Group to any third party, as stated in the financial statements then most
recently required to be delivered pursuant to Clause 12.1.1. 
 “Drillships 1837/1838” means the drillship
newbuildings currently under construction at the yard of the Drillships Builder with hull number 1837, scheduled for delivery on December 2010 and hull number 1838, scheduled for delivery on March 2011 and “Drillship 1837/1838”
means either of them. 
 “Drillships 1865/1866” means the drillship newbuildings currently under construction
at the yard of the Drillships Builder with hull number 1865, scheduled for delivery on June 2011 and hull number 1866, scheduled for delivery on September 2011 and “Drillship 1865/1866” means either of them. 
 “Drillships Builder” means Samsung Heavy Industries Co., Ltd. of the Republic of Korea. 
 “Drillship Milestones” means the financing of the following instalments under the building contracts in relation to the
Drillships 1837/1838:- 
  

	 	(a)	to be arranged on or before 15 February 2010 in relation to the fourth instalment under the relevant building contract in respect of hull number 1837 in the amount
of $110,422,472 due on 15 February 2010; 

  

	 	(b)	to be arranged on or before 15 June 2010 in relation to the fourth instalment under the relevant building contract in respect of hull number 1838 in the amount of
$110,422,472 due on 15 June 2010; 

  

	 	(c)	to be arranged on or before 15 September 2010 in relation to the fifth (delivery) instalment under the relevant building contract in respect of hull number 1837 in
the amount of $291,881,013 due on 15 December 2010; and 

  

	 	(d)	to be arranged on or before 15 December 2010 in relation to the fifth (delivery) instalment under the relevant building contract in respect of hull number 1838 in
the amount of $288,874,107 due on 15 March 2011. 

  

 7 

 Any of the above dates can be moved to a later date in accordance with any deferral of the
relevant repayment instalments as may be agreed with the Drillships Builder PROVIDED THAT evidence of such agreement in form and substance acceptable to the Lenders are provided to the Agent not later than three (3) Business Days prior to the
dates when the relevant instalments are due. 
 “Earnings Accounts” means the bank accounts opened in the names
of the Borrowers with the Agent and designated respectively “Ionian Traders Inc.—Earnings Account” and “Norwalk Star Owners Inc.—Earnings Account” and each an “Earnings Account”. 
 “Employment Requirements” means in respect of each of the Drillships 1837/1838 an employment contract being in place not
later than six (6) months prior to the delivery date of a Drillship 1837/1838, which covers fully that Drillship’s 1837/1838 Debt Service of a period of duration of at least three (3) years. 
 “First Supplemental Agreement” means the first supplemental agreement entered or to be entered into by and between the
Borrowers, the Lenders, the Swap Providers, the Agent and the Security Agent.” 
 “Fleet Market Value”
means the aggregate of the value of the Fleet Vessels based on the average of two valuations for each Fleet Vessel prima facie determined by a reputable, independent and first class firm of shipbrokers appointed by and reporting to the Agent on
the basis of a charter-free sale for prompt delivery for cash at arm’s length on normal commercial terms as between a willing seller and a willing buyer. 
 “Fleet Vessels” means any vessel (including, without limitation, any drill-ships owned or ordered by any member of the Group) from time to time owned more than fifty per cent
(50%) by any member of the Group. 
 “Group” means each of the Borrowers, the Guarantor and each of their
direct or indirect Subsidiaries. 
 “Mortgage Amendments” means the amendments to the Mortgages in favour of
the Security Agent in such form and containing such terms and conditions as the Security Agent shall require, and “Mortgage Amendment” means any one of them. 
  

 8 

 “New Investment” means any further investments or capital expenditure
other than any Permitted Investments or the maintenance of the Fleet Vessels in the ordinary course of business, PROVIDED THAT:- 
  

	 	(a)	the equity portion of any such further investments has been raised from proceeds of equity offerings; and 

  

	 	(b)	the Guarantor maintains Cash in an amount not less than eighty million Dollars ($80,000,000); and 

  

	 	(c)	any such investments shall be made on normal arms’ length terms and on terms consistent with the conditions applying in the applicable market at the relevant
time.” 

 “Operating Expenses” means expenses properly and reasonably incurred by a member
of the Group in connection with the operation, employment, maintenance, repair and insurance of a Fleet Vessel. 
 “Permitted Investments” means the building contracts relating to the newbuilding vessels:- 
  

	 	(a)	the panamax bulk carriers m.v. “OLIVA” (ex hull number 1519A), delivered in August 2009 and registered under the flag of the Republic of Malta and m.v.
“RAPALLO” (ex hull number 1518A), delivered in June 2009 and registered under the flag of the Republic of Malta; 

  

	 	(b)	the Drillships 1865/1866; and 

  

	 	(c)	the Drillships 1837/1838 PROVIDED THAT evidence in form and substance satisfactory to the Lenders has been provided that (i) the Drillships Milestones and
(ii) the Employment Requirements are met. 

 “Subsidiaries” means any company or entity
directly or indirectly controlled by such person, and for this purpose “control” means either the ownership of more than fifty per cent (50%) of the voting share capital (or equivalent rights of ownership) of such company or entity or
the power to direct its policies and management, whether by contract or otherwise and “Subsidiary” means any one of them. 
  

 9 

 “Waiver Period” means the period commencing on 1 January 2009 and
expiring at midnight 31 December 2010. 
  

	 	4.2	the definition of “Security Documents” set out in clause 1.1 of the Loan Agreement shall be amended so as to include the Additional Security Documents;

  

	 	4.3	the definition of “Margin” set out in clause 1.1 of the Loan Agreement shall be deleted and replaced as follows:- 

 “Margin” means:- 
  

	 	(a)	one point nine per cent (1 .9%) per annum during the Waiver Period; and 

  

	 	(b)	one point one five per cent (1.15%) per annum at all other times during the Facility Period. 

  

	 	4.4	clause 5.1 of the Loan Agreement shall be deleted and replaced as follows:- 

  

	 	“5.1	 Repayment of Loan The Borrowers agree to repay the Loan to the Agent for the account of the Lenders by thirty two (32) consecutive
quarterly instalments the first ten (1st- 10th) such repayment instalments each in the sum of six million five
hundred thousand Dollars ($6,500,000), the following twenty one (llth-31st) such
repayment instalments each in the sum of two million two hundred and fifty thousand Dollars ($2,250,000) and the thirty second (32nd) and final such repayment instalment in the sum of twelve million seven hundred and fifty thousand Dollars
($12,750,000) (comprising an instalment of two million two hundred and fifty thousand Dollars ($2,250,000) and a balloon amount of ten million five hundred thousand Dollars ($10,500,000)), the first instalment falling due on the date which is three
calendar months after the earlier to occur of the Second Drawdown Date and the Availability Termination Date and subsequent instalments falling due at consecutive intervals of three calendar months thereafter.”; 

  

	 	4.5	clause 10.4 of the Loan Agreement shall be deleted and replaced as follows:- 

  

	 	“10.4	 Additional security If at any time the aggregate of the Fair Market Value of the Vessels and the value of any additional security (such value to
be the face amount of the deposit (in the case of cash), determined conclusively by

  

 10 

	 	 
appropriate advisers appointed by the Agent (in the case of other charged assets), and determined by the Agent in its discretion (in all other cases)) for the time being provided to the Security
Agent under this Clause 10.4 is less than (a) seventy seven per cent (77%) of the Loan, for a period commencing from the beginning of the Waiver Period and ending on 30 June 2010 (inclusive), (b) ninety one per cent (91%) of
the Loan, from a period commencing on 1 July 2010 and ending on the end of the Waiver Period, and (c) one hundred and twenty five per cent (125%) of the Loan, at all other times during the Facility Period, the Borrowers shall, within
thirty (30) days of the Agent’s request, at the Borrowers’ option: 

  

	 	10.4.1	pay to the Security Agent or to its nominee a cash deposit in the amount of the shortfall to be secured in favour of the Security Agent as additional security for the
payment of the Indebtedness; or 

  

	 	10.4.2	give to the Security Agent other additional security in amount and form acceptable to the Security Agent in its discretion; or 

  

	 	10.4.3	prepay the amount of the Indebtedness which will ensure that the aggregate of the Fair Market Value of the Vessels and the value of any such additional security is not
less than (a) seventy seven per cent (77%) of the Loan, for a period commencing from the beginning of the Waiver Period and ending on 30 June 2010 (inclusive), (b) ninety one per cent (91%) of the Loan, from a period
commencing on 1 July 2010 and ending on the end of the Waiver Period, and (c) one hundred and twenty five per cent (125%) of the Loan, at all other times during the Facility Period. 

 Clauses 5.3 (Reborrowing), 6.2.3 (Voluntary prepayment of Loan) and 6.4 (Restrictions) shall apply, mutatis
mutandis, to any prepayment made under this Clause 10.4 and the value of any additional security provided shall be determined as stated above,”; 
  

 11 

	 	4.6	clause 12.2 (Financial covenants) of the Loan Agreement shall be deleted and replaced as follows:- 

  

	 	“12.2	Financial covenants The Borrowers shall procure that at all times the Guarantor’s financial condition, as evidenced by the most recent financial statements,
shall be such that: 

  

	 	12.2.1	the Guarantor maintains Interest Coverage which exceeds (a) 2:1 throughout the Waiver Period and (b) 3:1 at all other times during the Facility Period; and

  

	 	12.2.2	Minimum Net Worth is not lower than:- 

  

	 	(a)	one hundred and eighty million Dollars ($180,000,000) for the financial year ending 31 December 2008; 

  

	 	(b)	one hundred million Dollars ($100,000,000) for the financial year ending 31 December 2009; 

  

	 	(c)	one hundred and fifty million Dollars ($150,000,000) plus the net quarterly profits of the Guarantor, as evidenced by the Guarantor’s most recent financial
statements supplied to the Agent pursuant to Clause 12.1.1 from 1 January 2010 and until the end of the Waiver Period; 

  

	 	(d)	two hundred and twenty five million Dollars ($225,000,000) thereafter; and 

  

	 	12.2.3	throughout the Facility Period the Guarantor maintains aggregate Minimum Liquidity in an amount in excess of thirty five million Dollars ($35,000,000); and

  

	 	12.2.4	the Guarantor maintains a Market Adjusted Equity Ratio of:- 

  

	 	(a)	not lower than (i) twenty five per cent (25%) in respect of the financial year ending 31 December 2008 (ii) fifteen per cent (15%) throughout
the Waiver Period and (iii) forty per cent (40%) thereafter; or 

  

	 	(b)	not lower than five per cent (5%) PROVIDED THAT:- 

  

 12 

	 	(i)	the Agent, in its absolute discretion, determines that such fall in the Market Adjusted Equity Ratio has resulted from the reduction of the Fleet Market Value or the
mark to market position of any swap or other derivative transactions entered into by the Borrower and other members of the Group; and 

  

	 	(ii)	the Agent recalculates the Market Adjusted Equity Ratio on the basis of the Fleet Market Value and the mark to market position of any swap or other derivative
transactions entered into by the Borrower and other members of the Group as at 31 December 2008 to be at least fifteen per cent (15%). 

 The financial covenants contained in this Clause 12.2 shall be tested semi-annually on the basis of the annual financial statements provided under Clause 12.1.1 and shall be confirmed in the relevant
Compliance Certificate. For the avoidance of doubt, the financial covenants test on December 31, 2010 shall be based on the financial covenants during the Waiver Period as stipulated in Clauses 12.1.1, 12.2.2 and 12.2.4.”; 
  

	 	4.7	a new clause 12.3.19 shall be added in the Loan Agreement:- 

  

	 	“12.3.19	New Financial Indebtedness The Borrowers shall procure that, during the Waiver Period, any Financial Indebtedness incurred by either of the Borrowers or
any member of the Group shall only be used (a) to prepay any Financial Indebtedness secured on any asset of the Group and (b) in or towards financing any New Investment or any Permitted Investment PROVIDED THAT the equity contribution of
that Borrower or that member of the Group (as applicable) in such New Investment or Permitted Investment is no less than thirty two point five per cent (32.5%) of the acquisition cost such New Investment or Permitted Investment.”;

  

 13 

	 	4.8	a new clause 12.3.20 shall be added in the Loan Agreement:- 

  

	 	“12.3.20	New investment The Borrowers shall procure that, during the Waiver Period, the Guarantor or any other member of the Group does not enter into any further
investments or capital expenditure other than any Permitted Investments or the maintenance of the Fleet Vessels or any New Investment.”; 

  

	 	4.9	a new clause 12.3.21 shall be added in the Loan Agreement:- 

  

	 	“12.3.21	Shares The Borrowers shall procure that, during the Waiver Period, Mr. George Economou does not divest any of his interests in any of the issued shares in
the Guarantor which were held on 1 November 2009.”; 

  

	 	4.10	a new clause 12.3.22 shall be added in the Loan Agreement:- 

  

	 	“12.3.22	Disposal of assets The Borrowers shall procure that the Guarantor does not spin-off or otherwise dispose of any of its assets unless:- 

 

	 	(a)	the Guarantor maintains Cash in an amount not less than eighty million Dollars ($80,000,000); and 

  

	 	(b)	such disposal or spin-off is conducted on arm’s length basis on current market conditions; and 

  

	 	(c)	the Guarantor is released from all its obligations relating to the offshore business of the Group except the guarantee granted in favour of Deutsche Bank AG, relating
to the pre- and post delivery financing of the Drillships 1865/1866; and 

  

	 	(d)	the Guarantor secures six (6) months prior to the delivery of each Drillship 1865/1866 an employment contract which covers fully each that Drillship’s
1865/1866 Operating Expenses and Debt Service of a period of duration of at least two (2) years; and 

  

	 	(e)	the Guarantor uses its best endeavours to be released from its obligations under the guarantee granted in favour of Deutsche Bank AG, relating to the pre- and post
delivery financing of the Drillships 1865/1866.” 

  

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	 	4.11	a new clause 12.3.23 shall be added in the Loan Agreement:- 

  

	 	“12.3.23	No dividends during Waiver Period During the Waiver Period the Borrowers shall not and shall procure that the Guarantor and any member of the Group shall not pay
any dividends or make any other distribution to shareholders (including, but not limited to, any stock buyback). In respect of the payment of dividends relating to any disposal of assets or spin-off by the Guarantor Clause 12.3.22 (Disposal of
Assets) shall apply.”; 

  

	 	4.12	clause 6.6 of the Guarantee shall be deleted and replaced as follows:- 

  

	 	“6.6	The Guarantor covenants that, throughout the Facility Period its financial condition, as evidenced by the most recent financial statements, shall be such that:

  

	 	6.6.1	the Guarantor maintains Interest Coverage which exceeds (a) 2:1 throughout the Waiver Period and (b) 3:1 at all other times during the Facility Period; and

  

	 	6.6.2	the Guarantor’s Minimum Net Worth is not lower than:- 

  

	 	(a)	one hundred and eighty million Dollars ($180,000,000) for the financial year ending 31 December 2008; 

  

	 	(b)	one hundred million Dollars ($100,000,000) for the financial year ending 31 December 2009; 

  

	 	(c)	one hundred and fifty million Dollars ($150,000,000) plus the net quarterly profits of the Guarantor, as evidenced by the Guarantor’s most recent financial
statements supplied to the Agent pursuant to Clause 6.4 from 1 January 2010 and until the end of the Waiver Period; 

  

	 	(d)	two hundred and twenty five million Dollars ($225,000,000) thereafter; and 

  

 15 

	 	6.6.3	throughout the Facility Period the Guarantor maintains aggregate Minimum Liquidity in an amount in excess of thirty five million Dollars ($35,000,000); and

  

	 	6.6.4	the Guarantor maintains a Market Adjusted Equity Ratio of:- 

  

	 	(a)	not lower than (i) twenty five per cent (25%) in respect of the financial year ending 31 December 2008 (ii) fifteen per cent (15%) throughout
the Waiver Period and (iii) forty per cent (40%) thereafter; or 

  

	 	(b)	not lower than five percent PROVIDED THAT:- 

  

	 	(i)	the Agent, in its absolute discretion, that such fall in the Market Adjusted Equity Ratio has resulted from the reduction of the Fleet Market Value or the mark-market
position of any swap or other derivative transactions entered into by the Borrower and other members of the Group; and 

  

	 	(ii)	the Agent recalculates the Market Adjusted Equity Ratio on the basis of the Fleet Market Value and the mark-market position of any swap or other derivative transactions
entered into by the Borrower and other members of the Group as at 31 December 2008 to be at least fifteen per cent (15%). 

 The financial covenants contained in this Clause 6.6 shall be tested annually on the basis of the annual financial statements provided under Clause 6.4. For the avoidance of doubt, the financial covenants
test on December 31, 2010 shall be based on the financial covenants during the Waiver Period as stipulated in Clauses 6.6.1, 6.6.2 and 6.6.4.”; 
  

	 	4.13	a new clause 6.7 shall be added in the Guarantee:- 

  

	 	“6.7	 New Financial Indebtedness The Guarantor shall procure that, during the Waiver Period, any Financial Indebtedness incurred by either of
the Borrowers or any member of the Group shall only be

  

 16 

	 	 
used (a) to prepay any Financial Indebtedness secured on any asset of the Group and (b) in or towards financing any New Investment or any Permitted Investment.”;

  

	 	4.14	a new clause 6.8 shall be added in the Guarantee:- 

  

	 	“6.8	New investment The Guarantor shall not and shall procure that, during the Waiver Period, any other member of the Group does not, enter into any further
investments or capital expenditure other than any Permitted Investments or the maintenance of the Fleet Vessel or any New Investment.”; 

  

	 	4.15	a new clause 6.9 shall be added in the Guarantee:- 

  

	 	“6.9	Shares The Guarantor shall procure that, during the Waiver Period, Mr. George Economou does not divest any of his interests in any of the issued shares
which were held on 1 November 2009 in the Guarantor.”; 

  

	 	4.16	a new clause 6.10 shall be added in the Guarantee:- 

  

	 	“6.10	Disposal of assets The Guarantor shall not, and shall procure that no member of the Group shall not, spin-off or otherwise dispose of any of its assets any
unless:- 

  

	 	(a)	the Guarantor maintains Cash in an amount not less than eighty million Dollars ($80,000,000); and 

  

	 	(b)	such disposal or spin-off is conducted on arm’s length basis on current market conditions; and 

  

	 	(c)	the Guarantor is released from all its obligations relating to the offshore business of the Group except the guarantee granted in favour of Deutsche Bank AG, relating
to the pre- and post delivery financing of the Drillships 1865/1866; and 

  

	 	(d)	the Guarantor secures six (6) months prior to the delivery of each Drillship 1865/1866 an employment contract which covers fully each that Drillship’s
1865/1866 Operating Expenses and Debt Service of a period of duration of at least two (2) years; and 

  

 17 

	 	(e)	the Guarantor uses its best endeavours to be released from its obligations under the guarantee granted in favour of Deutsche Bank AG, relating to the pre- and post
delivery financing of the Drillships 1865/1866.”; 

  

	 	4.17	a new clause 6.11 shall be added in the Guarantee:- 

  

	 	“6.11	No dividends during Waiver Period During the Waiver Period the Guarantor shall not and shall procure that any member of the Group shall not pay any dividends or
make any other distribution to shareholders (including, but not limited to, any stock buyback). In respect of the payment of dividends relating to any disposal of assets or spin-off by the Guarantor Clause 6.10 (Disposal of Assets’)
shall apply “. 

 All other terms and conditions of the Loan Agreement and the Security Documents shall
remain unaltered and in full force and effect. 
  

	5	Confirmation and Undertaking 

  

	 	5.1	Each of the Security Parties confirms that all of its respective obligations under or pursuant to each of the Security Documents to which it is a party remain in full
force and effect, despite the amendments to the Loan Agreement made in this Supplemental Agreement, as if all references in any of the Security Documents to the Loan Agreement were references to the Loan Agreement as amended and supplemented by this
Supplemental Agreement. 

  

	 	5.2	The definition of any term defined in any of the Security Documents shall, to the extent necessary, be modified to reflect the amendments to the Loan Agreement made in
or pursuant to this Supplemental Agreement. 

  

	6	Communications, Law and Jurisdiction 

 The provisions of clauses 19 and 24 of the Loan Agreement shall apply to this Supplemental Agreement as if they were set out in full and as if references to the Loan Agreement were references to this
Supplemental Agreement and references to the Borrower were references to the Security Parties. 
  

 18 

 Schedule 1 
 The Lenders, the Commitments and the Swap Providers 
  

						
	 The Lenders
	  	The Commitments	  	 
			
	 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT
	  	$	62,500,000	  	
	  
 Domshof 17
	  			  	
	28195 Bremen	  			  	
	Federal Republic of Germany	  			  	
	Fax no: 0049 421 3609329	  			  	
	Contact Person: Loan Department	  			  	
			
	UNICREDIT BANK AG	  			  	
			
	 (formerly known as Bayerische Hypo- und Vereinsbank AG)
	  	$	62,500,000	  	
	Alter Wall 22	  			  	
	D-20457 Hamburg	  			  	
	Federal Republic of Germany	  			  	
			
	Fax No.: +49 40 3692 3696	  			  	
	Contact Person: Mr. Jan-Philipp Kathmann	  			  	
			
	 The Swap Providers
	  	 	  	 
			
	 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT
  
 Domshof 17
 28195 Bremen
 Federal Republic of Germany
 Fax no: 0049 421
3609329
 Contact Person: Loan Department
	  			  	
			
	UNICREDIT BANK AG	  			  	
	  
 (formerly known as Bayerische Hypo- und Vereinsbank AG)

Alter Wall 22
 D-20457 Hamburg
 Federal Republic of Germany
 Fax No.: +49 40 3692
3696
 Contact Person: Mr. Jan-Philipp Kathmann
	  			  	

  

 19 

 Schedule 2 
 Effective Date Confirmation 
  

	To:	NORWALK STAR OWNERS INC. 

 IONIAN TRADERS INC. 
 Trust Company Complex 
 Ajeltake Road 
 Ajeltake Island 
 Majuro 
 Marshall Islands MH 96960 
 We, DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT, refer to the
supplemental agreement dated             2010 (the “Supplemental Agreement”) relating to a secured loan agreement dated 13 May 2008 (the “Loan Agreement”)
made between you as the Borrower, the banks listed in it as the Lenders, ourselves as the Agent the banks listed in it as the Swap Providers and ourselves as the Security Agent in respect of a loan to you from the Lenders of up to $125,000,000,

 We hereby confirm that all conditions precedent referred to in Clause 2.1 of the Supplemental Agreement have been satisfied. In accordance
with Clauses 1,1 and 4 of the Supplemental Agreement the Effective Date is the date of this confirmation and the amendments to the Loan Agreement are now effective. 
  

							
	Dated:	 		 	                             2010

			
	Signed:	 	  
	 	
		 		 	 For and on behalf of
  
 DEUTSCHE SCHIFFSBANK AKTIENGESELLSCHAFT

		 		 

  

 20 

 IN WITNESS of which the parties to this Supplemental Agreement have executed this Supplemental
Agreement as a deed the day and year first before written. 
  

					
	SIGNED and DELIVERED as	  	)	  	 /s/ Eugenia Papapontikou

	a DEED by	  	)	  
	IONIAN TRADERS INC.	  	)	  
	acting by	  	)	  
	Eugenia Papapontikou	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  	
	Constantinos Karachalios	  		  	
	  
 /s/ Stephenson Harwood
	  		  	
	 STEPHENSON HARWOOD
 ARISTON
BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	
			
	SIGNED and DELIVERED as	  	)	  	  
 /s/ Eugenia Papapontikou
  

	a DEED by	  	)	  
	NORWALK STAR OWNERS INC.	  	)	  
	acting by	  	)	  
	Eugenia Papapontikou	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  
			
	SIGNED and DELIVERED as	  	)	  	/s/ Eugenia Papapontikou
	a DEED by	  	)	  
	DRYSHIPS INC.	  	)	  
	acting by	  	)	  
	Eugenia Papapontikou	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	

  

 21 

					
	SIGNED and DELIVERED as	  	)	  	/s/ Christodoulos Vartzis
	a DEED by	  	)	  
	DEUTSCHE SCHIFFSBANK	  	)	  
	AKTIENGESELLSCHAFT (as a Lender)	  	)	  
	acting by	  	)	  
	Christodoulos Vartzis	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	
			
	SIGNED and DELIVERED as	  	)	  	/s/ Christodoulos Vartzis
	a DEED by	  	)	  
	UNICREDIT BANK AG	  	)	  
	(formerly known as BAYERISCHE	  	)	  
	HYPO- UND VEREINSBANK AG)	  	)	  
	(as a Lender)	  	)	  
	acting by	  	)	  
	Christodoulos Vartzis	  	)	  
	its duly authorised attorney- in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	
			
	SIGNED and DELIVERED as	  	)	  	/s/ Christodoulos Vartzis
	a DEED by	  	)	  
	DEUTSCHE SCHIFFSBANK	  	)	  
	AKTIENGESELLSCHAFT (as Agent)	  	)	  
	acting by	  	)	  
	Christodoulos Vartzis	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	

  

 22 

					
	SIGNED and DELIVERED as	  	)	  	/s/ Christodoulos Vartzis
	a DEED by	  	)	  
	DEUTSCHE SCHIFFSBANK	  	)	  
	AKTIENGESELLSCHAFT	  	)	  
	(as a Swap Provider)	  	)	  
	acting by	  	)	  
	Christodoulos Vartzis	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	
			
	SIGNED and DELIVERED as	  	)	  	/s/ Christodoulos Vartzis
	a DEED by	  	)	  
	UNICREDIT BANK AG	  	)	  
	(formerly known as BAYERISCHE	  	)	  
	HYPO- UND VEREINSBANK AG)	  	)	  
	(as a Swap Provider)	  	)	  
	acting by	  	)	  
	Christodoulos Vartzis	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  	
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	
			
	SIGNED and DELIVERED as	  	)	  	/s/ Christodoulos Vartzis
	a DEED by	  	)	  
	DEUTSCHE SCHIFFSBANK	  	)	  
	AKTIENGESELLSCHAFT	  	)	  
	(as SecurityAgent)	  	)	  
	acting by	  	)	  
	Christodoulos Vartzis	  	)	  
	its duly authorised attorney-in-fact	  	)	  
	in the presence of:	  	)	  
	Constantinos Karachalios	  		  
	  
 /s/ Stephenson Harwood
 STEPHENSON HARWOOD
 ARISTON BUILDING
 2 FILELLINON STR. & AKTI MIAOULI
 PIRAEUS 18536
 VAT. NO. 998711156
 TEL 2104295160
	  		  	

  

 23First Supplemental Agreement, dated October 8, 2009

 Exhibit 4.46 
 Dated 8 October 2009 
 AEGEAN TRADERS INC. and

 IGUANA SHIPPING COMPANY LIMITED 
 as Borrowers 
 - and - 
 DRYSHIPS INC. 
 as Corporate Guarantor 
 - and - 
 WESTLB
AG, LONDON BRANCH 
 as Lender 
  
  
 FIRST
SUPPLEMENTAL AGREEMENT 
  
  
 in relation to a Loan Agreement dated 20 June 2008 
 in respect of a loan facility of (originally) up to US$103,200,000 
 and a Guarantee
also dated 20 June 2008 
 WATSON, FARLEY & WILLIAMS 
 Piraeus 

 INDEX 
  

					
	 Clause
	  	 	  	Page
			
	 1
	  	DEFINITIONS	  	2
			
	 2
	  	REPRESENTATIONS AND WARRANTIES	  	2
			
	 3
	  	AGREEMENT OF THE LENDER	  	3
			
	 4
	  	CONDITIONS	  	4
			
	 5
	  	VARIATIONS TO LOAN AGREEMENT AND FINANCE DOCUMENTS	  	5
			
	 6
	  	CONTINUANCE OF LOAN AGREEMENT AND FINANCE DOCUMENTS	  	12
			
	 7
	  	EXPENSES	  	13
			
	 8
	  	COMMUNICATIONS	  	13
			
	 9
	  	SUPPLEMENTAL	  	13
			
	 10
	  	LAW AND JURISDICTION	  	13
		
	 SCHEDULE 1
	  	14
		
	 FORM OF COMPLIANCE CERTIFICATE
	  	14

 THIS FIRST SUPPLEMENTAL AGREEMENT is dated 8 October 2009 and made 
 BETWEEN: 
  

	(1)	AEGEAN TRADERS INC., a corporation incorporated in the Marshall Islands whose registered office is at Trust Company Complex, Ajeltake Road, Ajeltake Island,
Majuro, Marshall Islands MH 96960 and IGUANA SHIPPING COMPANY LIMITED, a company incorporated in Malta whose registered office is at 5/1, Merchants Street, Valletta, Malta (together the “Borrowers” and each a
“Borrower”); 

  

	(2)	DRYSHIPS INC., a corporation incorporated in the Marshall Islands whose registered office is at Trust Company Complex, Ajeltake Road, Ajeltake Island, Majuro,
Marshall Islands MH 96960 (the “Corporate Guarantor”); and 

  

	(3)	WESTLB AG, LONDON BRANCH, a company incorporated in Germany having its registered office at Herzogstrasse 15 in 40217 Duesseldorf, Germany and acting through its
London branch at Woolgate Exchange, 25 Basinghall Street, London EC2V 5HA, England (as “Lender”). 

 BACKGROUND 
  

	(A)	By a Loan Agreement dated 20 June 2008 (the “Loan Agreement”) made between (i) the Borrowers as joint and several borrowers and (ii) the
Lender as lender whereby the Lender has made available to the Borrowers a loan facility of (originally) up to One hundred and Three million two hundred thousand United States Dollars (US$103,200,000) (the “Loan”) upon the terms and
for the purposes therein specified. 

  

	(B)	By a Guarantee dated 20 June 2008 (the “Corporate Guarantee”); 

  

	(C)	The Borrowers and the Corporate Guarantor have requested that the Lender agrees to (inter alia): 

  

	 	(a)	waive the application of the security cover provisions in clause 14.1 of the Loan Agreement during the period commencing on the Effective Date and ending on the earlier
of (i) the date on which the Lender is satisfied that the Corporate Guarantor and the Borrowers are in compliance with Clause 11.15 of the Corporate Guarantee and Clause 14.1 of the Loan Agreement and (ii) the date falling 18 months after
the date of this First Supplemental Agreement (the “Waiver Period”); 

  

	 	(b)	waive the application of the Corporate Guarantor’s financial covenants regarding the Market Adjusted Equity Ratio and Market Value Adjusted Net Worth set out in
paragraphs (a) and (c) respectively of clause 11.15 of the Corporate Guarantee during the Waiver Period; 

  

	 	(c)	relax, during the Waiver Period, the minimum Interest Coverage Ratio which needs to be maintained pursuant to paragraph (b) of clause 11.15 of the Corporate
Guarantee from 3:1 to 2:1; and 

  

	 	(d)	the amendment and/or variation of certain other provisions of the Loan Agreement and the other Finance Documents. 

  

	(D)	This Agreement sets out the terms and conditions on which the Lender agrees to: 

  

	 	(i)	 waive the application of clause 14.1 of the Loan Agreement during the Waiver Period and waive the Corporate Guarantor’s financial covenants
regarding the

	 	 
Market Adjusted Equity Ratio and Market Value Adjusted Net Worth set out in paragraphs (a) and (c) respectively of clause 11.15 of the Corporate Guarantee during the Waiver Period;

  

	 	(b)	amend the minimum Interest Coverage Ratio which needs to be maintained pursuant to paragraph (b) of clause 11.15 of the Corporate Guarantee from 3:1 to 2:1 for the
duration of the Waiver Period; 

  

	 	(c)	the consequential amendments to the Loan Agreement and the other Finance Documents in connection with those matters; and 

  

	 	(d)	certain other amendments and/or variations to the Loan Agreement and the other Finance Documents. 

 NOW THEREFORE IT IS HEREBY AGREED 
  

	1	DEFINITIONS 

  

	1.1	Words and expressions defined in the Loan Agreement (as hereby amended) and the recitals hereto and not otherwise defined herein shall have the same meanings
when used in this First Supplemental Agreement. 

  

	1.2	In this First Supplemental Agreement the words and expressions specified below shall have the meanings attributed to them below: 

 “Effective Date” means the date on which the conditions precedent in Clause 4 are satisfied; 
 “Mortgage Addendum” means, in relation to each Ship, the first addendum to the Mortgage on that Ship, executed or to be
executed by the Borrower owning that Ship in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both of them; and 
 “Waiver Period” has the meaning ascribed to it in Recital (C)(a) above. 
  

	1.3	Where the context so admits words importing the singular number only shall include the plural and vice versa and words importing persons shall include firms and
corporations. Clause headings are inserted for convenience of reference only and shall be ignored in construing this First Supplemental Agreement. References to Clauses are to clauses of this First Supplemental Agreement save as may be otherwise
expressly provided in this First Supplemental Agreement. 

  

	2	REPRESENTATIONS AND WARRANTIES 

  

	2.1	Each Borrower and the Corporate Guarantor hereby jointly and severally represents and warrants to the Lender, as at the date of this First Supplemental Agreement, that
the representations and warranties set forth in Clause 9 of the Loan Agreement and those set forth in clause 10 of the Corporate Guarantee (updated mutatis mutandis to the date of this First Supplemental Agreement) are true and correct as if all
references therein to “this Agreement” or, as the case may be, “this Guarantee” were references to the Loan Agreement or, as the case may be, the Corporate Guarantee as further amended by this First Supplemental Agreement.

  

	2.2	Each Borrower and the Corporate Guarantor hereby further jointly and severally represents and warrants to the Lender that as at the date of this First Supplemental
Agreement: 

  

	(a)	each of Aegean and the Corporate Guarantor is duly incorporated, validly existing and in goodstanding under the laws of the Marshall Islands and Iguana is duly
incorporated and validly existing and in good standing under the laws of Malta and each Borrower and the Corporate Guarantor has full power to enter into and perform its obligations under this First Supplemental Agreement and has complied with all
statutory and other requirements relative to its business, and does not have an established place of business in any part of the United Kingdom or the United States of America; 

  

 2 

	(b)	all necessary governmental or other official consents, authorisations, approvals, licences, consents or waivers for the execution, delivery, performance, validity
and/or enforceability of this First Supplemental Agreement and all other documents to be executed in connection with the amendments to the Loan Agreement and the Corporate Guarantee as contemplated hereby have been obtained and will be maintained in
full force and effect, from the date of this First Supplemental Agreement and so long as any moneys are owing under any of the Finance Documents and while all or any part of the Commitment remains outstanding; 

  

	(c)	each Borrower and the Corporate Guarantor has taken all necessary corporate and other action to authorise the execution, delivery and performance of its obligations
under this First Supplemental Agreement and such other documents to which it is a party and such documents do or will upon execution thereof constitute the valid and binding obligations of each Borrower and the Corporate Guarantor enforceable in
accordance with their respective terms; 

  

	(d)	the execution, delivery and performance of this First Supplemental Agreement and all such other documents as contemplated hereby does not and will not, from the date of
this First Supplemental Agreement and so long as any moneys are owing under any of the Finance Documents and while all or any part of the Commitment remains outstanding, constitute a breach of any contractual restriction or any existing applicable
law, regulation, consent or authorisation binding on each Borrower and the Corporate Guarantor or on any of its property or assets and will not result in the creation or imposition of any security interest, lien, charge or encumbrance (other than
under the Finance Documents) on any of such property or assets; and 

  

	(e)	each Borrower and the Corporate Guarantor has fully disclosed in writing to the Lender all facts which it knows or which it should reasonably know and which are
material for disclosure to the Lender in the context of this First Supplemental Agreement and all information furnished by such Borrower or the Corporate Guarantor or on its behalf relating to its business and affairs in connection with this First
Supplemental Agreement was and remains true, correct and complete in all material respects and there are no other material facts or considerations the omission of which would render any such information misleading. 

  

	3	AGREEMENT OF THE LENDER 

  

	3.1	The Lender, relying upon each of the representations and warranties set out in Clauses 2.1 and 2.2 of this First Supplemental Agreement, hereby agrees with the
Borrowers and the Corporate Guarantor, subject to and upon the terms and conditions of this First Supplemental Agreement and in particular, but without limitation, subject to the fulfilment of the conditions precedent set out in Clause 4, to:

  

	(a)	waive the application of the security cover provisions in clause 14.1 of the Loan Agreement during the Waiver Period; 

  

	(b)	waive the application of the Corporate Guarantor’s financial covenants regarding the Market Adjusted Equity Ratio and Market Value Adjusted Net Worth set out in
paragraphs (a) and (c) respectively of clause 11.15 of the Corporate Guarantee during the Waiver Period; and 

  

 3 

	(c)	the amendment and/or variation of certain other provisions of the Loan Agreement and the other Finance Documents. 

  

	3.2	Each Borrower and the Corporate Guarantor agrees and confirms that the Loan Agreement, the Corporate Guarantee and the other Finance Documents to which it is a party
shall remain in full force and effect and that Borrower and the Corporate Guarantor shall remain liable under the Loan Agreement, the Corporate Guarantee and the other Finance Documents to which it is a party for all obligations and liabilities
assumed by it thereunder. 

  

	3.3	The agreement of the Lender contained in Clauses 3.1 and 3.2 shall have effect on and from the Effective Date. 

  

	4	CONDITIONS 

  

	4.1	The agreements of the Lender contained in Clause 3.1 of this First Supplemental Agreement shall all be expressly subject to the condition that the Lender shall
have received in form and substance satisfactory to the Lender and its legal advisers on or before the Effective Date: 

  

	(a)	a certificate from an officer of each Borrower confirming the names of all the directors and shareholders of that Borrower and having attached thereto true and complete
copies of their incorporation and constitutional documents; 

  

	(b)	a certificate from an officer of the Corporate Guarantor confirming the names of all the directors of the Corporate Guarantor and having attached thereto true and
complete copies of its incorporation and constitutional documents; 

  

	(c)	true and complete copies of the resolutions passed at separate meetings of all the directors and shareholders of each Borrower authorising and approving the execution
of this First Supplemental Agreement and the Mortgage Addendum to which that Borrower is or will become a party and any other document or action to which it is or is to be a party and authorising its directors or other representatives to execute the
same on its behalf; 

  

	(d)	true and complete copies of the resolutions passed at a meeting of all the directors of the Corporate Guarantor authorising and approving the execution of this First
Supplemental Agreement and any other document or action to which it is or is to be a party and authorising its directors or other representatives to execute the same on its behalf; 

  

	(e)	the original of any power of attorney issued by each Borrower and the Corporate Guarantor pursuant to such resolutions aforesaid; 

  

	(f)	each Mortgage Addendum duly executed by the relevant Borrower together with evidence that that Mortgage Addendum has been duly registered as a valid addendum to the
relevant Mortgage in accordance with the laws of Malta; 

  

	(g)	certified copies of all documents (with a certified translation if an original is not in English) evidencing any other necessary action, approvals or consents with
respect to this First Supplemental Agreement and the Mortgage Addenda (including without limitation) all necessary governmental and other official approvals and consents in such pertinent jurisdictions as the Lender deems appropriate;

  

 4 

	(h)	such legal opinions as the Lender may require in respect of the matters contained in this First Supplemental Agreement and the Mortgage Addenda; and

  

	(i)	evidence that the agent referred to in clause 30.4 of the Loan Agreement has accepted its appointment as agent for service of process under this First Supplemental
Agreement and the Additional Finance Documents. 

  

	5	VARIATIONS TO LOAN AGREEMENT AND FINANCE DOCUMENTS 

  

	5.1	In consideration of the agreement of the Lender contained in Clause 3.1 of this First Supplemental Agreement the Borrowers and the Corporate Guarantor hereby agree with
the Lender that upon satisfaction of the conditions referred to in Clause 4.1, the provisions of the Loan Agreement and the Corporate Guarantee shall be varied and/or amended and/or supplemented as follows: 

  

	(a)	by inserting in clause 1.1 of the Loan Agreement and the Corporate Guarantee the definition of “Mortgage Addendum” set out in Clause 1.2 of this First
Supplemental Agreement; 

  

	(b)	the definition of, and references throughout each of the Finance Documents to, the Mortgage relevant to each Ship shall be construed as if the same referred to that
Mortgage as amended and supplemented by the relevant Mortgage Addendum; 

  

	(c)	by adding the following new definitions of “Additional Owner”, “Additional Ship”, “Approved Owner”, “Approved Ship”,
“Effective Date”, “MYSTIC”, “OREGON”, “Permitted Investment” and “Waiver Period” in clause 1.1 of the Loan Agreement: 

 ““Additional Owner” means each of: 
  

	 	(a)	in the case of “MYSTIC”, Dalian Star Owners Inc. a corporation incorporated in the Marshall Islands whose registered office is at Trust Company Complex,
Ajeltake Road, Ajeltake Island, Majuro, Marshall Islands MH 96960; and 

  

	 	(b)	in the case of “OREGON”, Iason Owning Company Limited a corporation incorporated in the Marshall Islands whose registered office is at Trust Company Complex,
Ajeltake Road, Ajeltake Island, Majuro, Marshall Islands MH 96960, 

 each a subsidiary of the Corporate Guarantor
and, in the plural, means both of them; 
 “Additional Ship” means each of “MYSTIC” and
“OREGON” and, in the plural, means both of them; 
 “Approved Owner” means, in respect of any Approved
Ship, the registered owner thereof (subject to such owner being incorporated in a jurisdiction acceptable to the Lender and being a subsidiary of the Corporate Guarantor) and, in the plural, means all of them; 
 “Approved Ship” means any kind of vessel to be in all respects (including, but not limited to, type, age or deadweight)
acceptable to the Lender owned by the relevant Approved Owner and, in the plural, means all of them; 
 “Effective
Date” means the date on which the conditions precedent in clause 4 of the First Supplemental Agreement are satisfied; 
 “First Supplemental Agreement” means the first supplemental agreement to this Agreement dated 8 October 2009 and entered into between the Borrowers, the Corporate Guarantor and the Lender; 
  

 5 

 “Hull 1837” means the drillship currently under construction by Samsung
pursuant to the Hull 1837 Shipbuilding Contract which is scheduled to be delivered in December 2010; 
 “Hull
1838” means the drillship currently under construction by Samsung pursuant to the Hull 1838 Shipbuilding Contract which is scheduled to be delivered in March 2011; 
 “Hull 1837 Shipbuilding Contract” means the shipbuilding contract dated 17 September 2007 (as the same may be amended
and supplemented from time to time) and executed between Drillship Hydra Owners Inc. and Samsung; 
 “Hull 1838
Shipbuilding Contract” means the shipbuilding contract dated 17 September 2007 (as the same may be amended and supplemented from time to time) and executed between Drillship Paros Owners Inc. and Samsung; 
 “Hull SS058” means the Kamsarmax bulk carrier of approximately 82,000 metric tons deadweight, currently under construction
by Tsuneishi pursuant to the SS058 MOA; 
 “Hull SS059” means the Kamsarmax bulk carrier with Hull Number SS059
of approximately 82,000 metric tons deadweight, currently under construction by Tsuneishi pursuant to the SS059 MOA; 
 “MYSTIC” means the 2008-built bulk carrier vessel of 89,510 gross registered tons and 56,668 net registered tons, having IMO Number 9421831 and registered in the ownership of the relevant Additional Owner under the Maltese
flag with the name “MYSTIC”; 
 “OREGON” means the 2002-built bulk carrier vessel of 38,727 gross
registered tons and 26,124 net registered tons, having IMO Number 9214123 and registered in the ownership of the relevant Additional Owner under the Maltese flag with the name “OREGON”; 
 ““Permitted Investment” means any investment or capital expenditure to be made by a Borrower or the Corporate
Guarantor: 
  

	 	(a)	in the ordinary course of its business for the purpose of maintaining the Ships (or either of them); 

  

	 	(b)	the equity portion of which shall have been raised from proceeds of any equity offering by the Corporate Guarantor; or 

  

	 	(c)	in connection with the acquisition and construction of Hull 1837, Hull 1838, Hull SS058 and Hull SS059; 

 “Samsung” means Samsung Heavy Industries Co. Ltd. a company organised under the laws of Korea with registered office at 34th
floor, Samsung Life Insurance Seocho Tower 1321-15, Seocho-Dong, Seocho-Gu, Seoul, Korea; 
 “SS058 MOA” means
the memorandum of agreement dated 31 July 2007 (as the same may be amended and supplemented from time to time) and executed between Iktinos Owning Company Limited and Chijin (as nominated by Tsuneishi Holdings Corporation Kambara Kisen
Company); 
 “SS059 MOA” means the memorandum of agreement dated 31 July 2007 (as the same may be amended
and supplemented from time to time) and executed between Kallikrates Owning Company Limited and Chijin (as nominated by Tsuneishi Holdings Corporation Kambara Kisen Company); 
  

 6 

 “Tsuneishi” means Tsuneishi Group (Zhoushan) Shipbuilding Inc. a company
organised under the laws of the People’s Republic of China with registered office at Retao Village, Xiushan Island, Daishan Country, Zhoushan City, Zhejiang Province, the Peoples’ Republic of China; 
 “Waiver Period” means the period commencing on the Effective Date and ending on the earlier of (i) the date on which
the Lender is satisfied that the Corporate Guarantor and the Borrowers are in compliance with Clause 11.15 of the Corporate Guarantee and Clause 14.1 of the Loan Agreement and (ii) the date falling 18 months after the date of the First
Supplemental Agreement;”; 
  

	(d)	by deleting the definition of “Margin” in clause 1.1 of the Loan Agreement and replacing it with the following new definition: 

 ““Margin” means: 
  

	 	(a)	during the Waiver Period, 2 per cent, per annum; and 

  

	 	(b)	at all times thereafter, 1.2 per cent per annum;”; 

  

	(e)	by deleting clause 10.6 of the Loan Agreement in its entirety and substituting it with the following: 

 “10.6 Provision of financial statements. The Borrowers will send or procure there are sent to the Lender: 
  

	 	(a)	as soon as possible, but in no event later than 180 days after the end of each financial year of the Borrowers and the Corporate Guarantor (in the case of the
management accounts or, if available, the audited financial statements for the Borrowers commencing with the financial year ending on 31 December 2008 and in the case of the audited consolidated financial statements the Corporate Guarantor
commencing with the financial year ending on 31 December 2007), the management accounts or, if available, the audited financial statements in respect of each of the Borrowers, and the audited consolidated financial statements in respect of the
Corporate Guarantor, in each case for that financial year; and 

  

	 	(b)	as soon as possible, but in no event later than 10 days after the end of each calendar month, cash flow statements in respect of each Borrower and the Corporate
Guarantor showing income received and the expenditure of that Borrower or the Corporate Guarantor in the previous calendar month.”; 

  

	(f)	by adding the following new sub-paragraph (g) in clause 11.3 of the Loan Agreement: 

 ““(g) during the Waiver Period, make any form of investments or capital expenditure other than the Permitted Investments.”;

  

	(g)	by adding a new clause 11.5 in the Loan Agreement as follows: 

 ““11.5 Additional Security. The Borrowers shall, promptly following the Lender’s request, at any time during the Waiver Period, procure that: 
  

	 	(a)	an Additional Owner executes or, as the case may be, registers in favour of the Lender as additional security for the obligations of the Borrowers under the Loan
Agreement and the other Finance Documents a second priority or as the case may preferred mortgage (and, if applicable, a collateral deed of covenants) over the Additional Ship owned by it together with a second priority assignment of the earnings
and insurances of the applicable Additional Ship; or 

  

 7 

	 	(b)	if for any reason the registration of the second priority security specified in (a) above is not possible, an Approved Owner executes or, as the case may be,
registers in favour of the Lender as additional security for the obligations of the Borrowers under the Loan Agreement and the other Finance Documents a second priority or as the case may preferred mortgage (and, if applicable, a collateral deed of
covenants) over the relevant Approved Ships together with a second priority assignment of the earnings and insurances of the applicable Additional Ship.”; 

  

	(h)	by adding a new clause 11.6 in the Loan Agreement as follows: 

 “11.6 Prepayments/provisions of cash security. The Borrowers shall ensure that if following the Effective Date the Corporate Guarantor and any other member of the Group make prepayments or
provide cash (or cash equivalent) security to any other banks or financial institutions (in respect of any Financial Indebtedness owed to such banks or financial institutions) in an amount of more than $15,000,000 in aggregate, the Borrowers shall
prepay an equal proportion of the Loan or provide equivalent cash (or cash equivalent) security in favour of the Lender.”; 
  

	(i)	by adding the words “(at any time other than during the Waiver Period)”: 

  

	 	(i)	after the word “Borrowers” in the second line of clause 14.1 of the Loan Agreement; and 

  

	 	(ii)	after the words “at any date” in the first line of clause 14.3 of the Loan Agreement; 

  

	(j)	by inserting the following new definitions in clause 1.1 of the Corporate Guarantee: 

 ““Delivery Date” means, in relation to each Permitted Ship, the date on which title to and possession of that Permitted
Ship is transferred to the relevant buyer pursuant to the relevant Permitted Shipbuilding Contract; 
 “Deutsche Bank
Borrowers” means Drillships Skopelos Owners Inc and Drillships Kithira Owners Inc, and in the singular means either of them; 
 “Deutsche Bank Loan Agreements” means, together: 
  

	 	(a)	the loan agreement dated 18 July 2008 made between (i) Drillships Skopelos Owners Inc as borrower, (ii) the banks and financial institutions listed as
lenders therein, (iii) Deutsche Bank AG, London branch and Dexia Credit Local, New York branch as swap banks, (iv) Deutsche Bank Luxembourg SA as facility agent, (v) Deutsche Bank AG Filiale Deutschlandgeschaft as security trustee,
(vi) Deutsche Bank AG, London branch and Dexia Credit Local, New York branch joint mandated lead arrangers and (vii) Deutsche Bank AG, London as bookrunner; and 

  

	 	(b)	the loan agreement dated 18 July 2008 made between (i) Drillships Kithira Owners Inc as borrower, (ii) the banks and financial institutions listed as
lenders therein, (iii) Deutsche Bank AG, London branch and Dexia Credit Local, New York branch as swap banks, (iv) Deutsche Bank Luxembourg SA as facility agent, (v) Deutsche Bank AG Filiale Deutschlandgeschaft as security trustee,
(vi) Deutsche Bank AG, London branch and Dexia Credit Local, New York branch joint mandated lead arrangers and (vii) Deutsche Bank AG, London as bookrunner, 

  

 8 

 and, in the singular, means either of them; 
 “Hull 1865” means the drillship currently under construction by Samsung pursuant to the 1865 Shipbuilding Contract which is
scheduled to be delivered in July 2011; 
 “Hull 1866” means the drillship currently under construction by
Samsung pursuant to the 1866 Shipbuilding Contract which is scheduled to be delivered in September 2011; 
 “Hull 1865
Shipbuilding Contract” means the shipbuilding contract dated 24 January 2008 (as the same may be amended and supplemented from time to time) and executed between Drillship Kithira Owners Inc. and Samsung; 
 “Hull 1866 Shipbuilding Contract” means the shipbuilding contract dated 24 January 2008 (as the same may be amended and
supplemented from time to time) and executed between Drillship Skopelos Owners Inc. and Samsung; 
 “Permitted
Ships” means, together, Hull 1865 and Hull 1866 and, in the singular means, either of them; 
 “Permitted
Shipbuilding Contracts” means, together, the Hull 1865 Shipbuilding Contract and the Hull 1866 Shipbuilding Contract and, in the singular, means either of them; 
 “Waiver Period” means the period commencing on the Effective Date and ending on the earlier of (i) the date on which the Lender is satisfied that the Guarantor and the Borrowers are
in compliance with Clause 11.15 of this Guarantee and clause 14.1 of the Loan Agreement and (ii) the date falling 18 months after the date of the First Supplemental Agreement;”;”; 
  

	(k)	by deleting clause 11.3 of the Corporate Guarantee in its entirety and substituting it with the following: 

  

	 	“11.3	Provision of financial statements. The Guarantor will send or procure there are sent to the Lender: 

  

	 	(a)	as soon as possible, but in no event later than 180 days after the end of each financial year of the Borrowers and the Guarantor (in the case of the management accounts
or, if available, the audited financial statements for the Borrowers commencing with the financial year ending on 31 December 2008 and in the case of the audited consolidated financial statements of the Guarantor commencing with the financial
year ending on 31 December 2007), (i) the management accounts or, if available, the audited financial statements in respect of the Borrowers and (ii) the audited consolidated financial statements of the Guarantor for that financial
year and such other financial information (including information as to its financial condition, commitments and operations) in connection with the Guarantor as the Lender may reasonably require; and 

  

	 	(b)	as soon as possible, but in no event later than 10 days after the end of each calendar month, a cash flow statement in respect of the Guarantor showing the income
received and the expenditure of the Guarantor in the previous calendar month.”; 

  

 9 

	(1)	by deleting clause 11.11(b) of the Corporate Guarantee and replacing it with the following: 

 “(b) pay any dividend or make any other form of distribution or effect any form of redemption or return of share capital Provided
that the Guarantor may in any financial year pay a dividend or make any other form of distribution which does not exceed in aggregate 50 per cent, of the Net Income for such financial year subject to (i) no Event of Default having
occurred which is continuing at the relevant time or resulting from the payment of a dividend or the making of any other form of distribution and (ii) any dividend during the Waiver Period being made by way of issue of shares only; or”;

  

	(m)	by adding the words “(other than any reconstruction or reorganisation which may occur in connection with a Spin Off” after the word “kind)” in the
second line of clause 11.11 (d) of the Corporate Guarantee; 

  

	(n)	by adding the following new sub-paragraph (e) in clause 11.11 of the Corporate Guarantee: 

  

	 	““(e)	during the Waiver Period, make any form of investments or capital expenditure other than any Permitted Investment.”; 

  

	(o)	by deleting clause 11.12(a) of the Corporate Guarantee and replacing it with the following: 

  

	 	“(a)	not, and shall procure that neither Borrower will, create or permit to arise any Security Interest over any asset present or future except (i) Security Interests
created or permitted by the Finance Documents, (ii) Permitted Security Interests and (iii) in the case of the Guarantor those arising: 

  

	 	(A)	during the Waiver Period, in connection with any Permitted Investments; or 

  

	 	(B)	at all times thereafter, in the normal course of its business of acquiring, financing and operating vessels and making investments within the shipping and oil and gas
sector,”; 

  

	(o)	by deleting clause 11.13 of the Corporate Guarantee in its entirety and replacing it with the following: 

  

	 	““11.13  No	disposal of assets and change of business. The Guarantor: 

  

	 	(a)	shall procure that neither Borrower will transfer, lease or otherwise dispose of all or a substantial part of its assets, whether by one transaction or a number of
transactions, whether related or not except in the usual course of its trading operations and on normal arms’ length terms; or 

  

	 	(b)	will not, and shall procure that neither Borrower make any substantial change to the nature of its business from that existing at the date of this Guarantee; or

  

	 	(c)	will not Spin Off the offshore business of the Group unless: 

  

	 	(i)	the Lender is satisfied that the Guarantor and all other members of the Group maintain and will continue to maintain bank or cash balances equal to at least $80,000,000
in aggregate; and 

  

 10 

	 	(ii)	it has delivered to the Lender evidence that each of Hull 1865 and Hull 1866 is subject to an Approved Contract of Employment commencing from the actual delivery date
of the relevant Permitted Ship or, if the Cut Off Date for such Permitted Ship has not occurred prior to Spin Off, the Guarantor shall by no later than that Cut Off Date deliver to the Lender such evidence as aforesaid; 

  

	 	(iii)	it provides satisfactory evidence to the Lender that it has been released from all its obligations relating to the offshore business of the Group (including, without
limitation, the $800,000,000 acquisition financing of Ocean Rig ASA (other than any obligations it has pursuant to two guarantees each dated 18 July 2008 executed by the Guarantor as security for the obligations of the Deutsche Bank Borrowers
under the Deutsche Bank Loan Agreements)); and 

  

	 	(iv)	it satisfies the Lender that it is using its best endeavours to be released from the guarantees referred to in paragraph (iii) above. 

 In this Clause 11.13(c) the following terms will have the following meanings: 
 “Approved Contract of Employment” means, in respect of each of Hull 1865 and Hull 1866, a contract of employment in respect
of that Permitted Ship for at least 24 months in duration (commencing from the delivery date of the relevant Permitted Ship) at a hire rate which, when aggregated for the first 24 months of the duration thereof will be in an amount of at least equal
to the aggregate of the (a) operating expenses and (b) debt service costs of that Permitted Ship for the first 24 months of the duration of that contract of employment. 
 “Cut Off Date” means, in respect of each of Hull 1865 and Hull 1866, the date falling 6 months prior to the scheduled
delivery date of that Permitted Ship; and 
 “Spin Off” means any means any reorganization, spin-off,
re-domiciliation or transfer of ownership in respect of any corporate entity whose business primarily consists of activities in the oil, gas and off shore sector;”; 
  

	(d)	by deleting clause 11.15 of the Corporate Guarantee in its entirety and replacing it with the following: 

  

	 	““11.15  Financial	covenants. The Guarantor shall ensure that at all times: 

  

	 	(a)	(other than during the Waiver Period) the Market Adjusted Equity Ratio shall not be less than 0.2:1; 

  

	 	(b)	the Interest Coverage Ratio shall not be less than: 

  

	 	(ii)	during the Waiver Period, 2:1; and 

  

	 	(iii)	at all times thereafter, 3:1; 

  

	 	(c)	(other than during the Waiver Period) the Market Value Adjusted Net Worth of the Group shall not be less than $250,000,000; and 

  

	 	(d)	there is available to the Guarantor and all the other members of the Group an aggregate amount of not less than $20,000,000 in immediately freely available and
unencumbered bank or cash balances.”; 

  

 11 

	(q)	by adding a new clause 11.18 in the Corporate Guarantee as follows: 

 “11.18 Prepayments/provisions of cash security. The Guarantor shall procure that the Borrowers shall, if following the Effective Date the Guarantor and any other member of the Group
make prepayments or provide cash (or cash equivalent) security to any other banks or financial institutions (in respect of any Financial Indebtedness of such banks or financial institutions) in an amount of more than $15,000,000 in aggregate, prepay
an equal proportion of the Loan or provide equivalent cash (or cash equivalent) security in favour of the Lender.”; 
  

	(r)	by amending the existing heading in Schedule 1 to the Corporate Guarantee to read “Part A - Form of Compliance Certificate (to be used except during Waiver
Period)” and adding at the end of Schedule 1 (as a new Part B to that Schedule) the form of Compliance Certificate set out in Schedule 1 to this First Supplemental Agreement; 

  

	(s)	by construing all references therein to “this Agreement” where the context admits as being references to “this Agreement as the same is amended and
supplemented by this First Supplemental Agreement and as the same may from time to time be further supplemented and/or amended”; and 

  

	(t)	by construing references to each of the Finance Documents as being references to each such document as it is from time to time supplemented and/or amended.

  

	5.2	Amendments to Finance Documents. With effect on and from the date of this First Supplemental Agreement each of the Finance Documents other than the Loan
Agreement shall be, and shall be deemed by this Agreement to have been, amended as follows: 

  

	(a)	the definition of, and references throughout each of the Finance Documents to, the Loan Agreement and any of the other Finance Documents shall be construed as if the
same referred to the Loan Agreement and those Finance Documents as amended and supplemented by this First Supplemental Agreement; and 

  

	(b)	by construing references throughout each of the Finance Documents to “this Agreement”, “this Deed”, “hereunder and other like expressions as if
the same referred to such Finance Documents as amended and supplemented by this First Supplemental Agreement. 

  

	5.3	Finance Documents to remain in full force and effect. The Finance Documents shall remain in full force and effect as amended and supplemented by:

  

	(a)	the amendments to the Finance Documents contained or referred to in Clauses 5.1 and 5.2; and 

  

	(b)	such further or consequential modifications as may be necessary to make the same consistent with, and to give full effect to, the terms of this First Supplemental
Agreement. 

  

	6	CONTINUANCE OF LOAN AGREEMENT AND FINANCE DOCUMENTS 

  

	6.1	Continuance of Loan Agreement and other Finance Documents. Save for the alterations to the Loan Agreement, the Corporate Guarantee and the other Finance
Documents made or to be made pursuant to this First Supplemental Agreement and such further modifications (if any) thereto as may be necessary to make the same consistent with the terms of this First Supplemental Agreement, the Loan Agreement and
the Corporate Guarantee shall remain in full force and effect and the security constituted by the other Finance Documents shall continue and remain valid and enforceable. 

  

 12 

	7	EXPENSES 

  

	7.1	Fees and expenses. The provisions of clause 19 (fees and expenses) of the Loan Agreement shall apply to this First Supplemental Agreement as if they were
expressly incorporated in this First Supplemental Agreement with any necessary amendments. 

  

	7.2	Restructuring fees. The Borrowers shall pay to the Lender on the date of this First Supplemental Agreement a restructuring fee of $ 167.750 ( representing
0.25 per cent of the Loan). 

  

	8	COMMUNICATIONS 

  

	8.1	General. The provisions of clause 27 (notices) of the Agreement, as amended and supplemented by this Agreement, shall apply to this Agreement as if they
were expressly incorporated in this Agreement with any necessary modifications. 

  

	9	SUPPLEMENTAL 

  

	9.1	Counterparts. This First Supplemental Agreement may be executed in any number of counterparts. 

  

	9.2	Third Party rights. A person who is not a party to this Agreement has no right under the Contracts (Rights of Third Parties) Act 1999 to enforce or to enjoy the
benefit of any term of this First Supplemental Agreement. 

  

	10	LAW AND JURISDICTION 

  

	10.1	Governing law. This First Supplemental Agreement shall be governed by and construed in accordance with English law. 

  

	10.2	Incorporation of the Agreement provisions. The provisions of clause 30 (law and jurisdiction) of the Agreement, as amended and supplemented by this First
Supplemental Agreement, shall apply to this First Supplemental Agreement as if they were expressly incorporated in this First Supplemental Agreement with any necessary medications. 

 IN WITNESS WHEREOF the parties hereto have caused this First Supplemental Agreement to be duly executed the day and year first above written.

  

 13 

 SCHEDULE 1 
 FORM OF COMPLIANCE CERTIFICATE 
 (to be used during the
Waiver Period) 
  

	To:	WestLB AG, London Branch 

 Wool
gate Exchange 
 25 Basinghall Street 
 London EC2V 5HA 
 England 
 [—] 200[—] 
 Dear Sirs, 
 We refer to: 
  

	(a)	a loan agreement dated 20 June 2008 (as amended and supplemented by a first supplemental agreement dated [—], the
“Loan Agreement”) made between (amongst others) yourselves and Aegean Traders Inc. and Iguana Snipping Company Limited (together, the “Borrowers”) in relation to a term loan facility of up to $103,200,000 in
aggregate; and 

  

	(b)	a guarantee dated [—] 2008 of the obligations of the Borrowers under (inter alia) the Loan Agreement.

 Words and expressions defined in the Loan Agreement shall have the same meaning when used in this compliance certificate.

 We enclose with this certificate a copy of the audited consolidated accounts for the Borrowers and ourselves for the financial year ended
[—]. The accounts (i) have been prepared in accordance with all applicable laws and generally accepted accounting information all consistently applied, (ii) give a true and fair view of the
state of affairs of the Group at the date of the accounts and of its profit for the period to which the accounts relate and (iii) fully disclose or provide for all significant liabilities of the Group. 
 We represent that no Event of Default or Potential Event of Default has occurred as at the date of this certificate [except for the following matter or
event [set out all material details of matter or event]]. In addition as of [—], we confirm compliance with the financial covenants set out in Clause 11.15 of the Guarantee for the financial
year ending as of the date to which the enclosed accounts are prepared. 
 We now certify that, as at [—]: 
  

	(a)	the Interest Coverage Ratio is [—]:[—]; and

  

	(b)	the aggregate freely available and unencumbered bank or cash balances of the Group are $[—]. 

 

 14 

 This certificate shall be governed by, and construed in accordance with, English law. 
  

	
	  

	[—]
	Authorised Signatory of DryShips Inc.

  

 15 

 EXECUTION PAGE 
  

							
	BORROWERS	 		 		 	
				
	SIGNED by    

	 		 	)	 	 /s/ Eugenia Papapontikou

		 		 	)	 
	for and on behalf of	 		 	)	 
	AEGEAN TRADERS INC.	 		 	)	 
	in the presence of:	 		 	)	 
				
	 /s/ Christoforos Bismpikos
 CHRISTOFOROS BISMPIKOS
 SOLICITOR
 WATSON, FARLEY & WILLIAMS
 89 AKTI MIAOULI
 PIRAEUS 18538 - GREECE
	 		 		 	
				
	SIGNED by    

	 		 	)	 	 /s/ Eugenia Papapontikou

		 		 	)	 
	for and on behalf of	 		 	)	 
	IGUANA SHIPPING COMPANY LIMITED	 		 	)	 
	in the presence of:	 		 	)	 
				
	 /s/ Christoforos Bismpikos
 CHRISTOFOROS BISMPIKOS
 SOLICITOR
 WATSON, FARLEY & WILLIAMS
 89 AKTI MIAOULI
 PIRAEUS 18538 - GREECE
	 		 		 	
				
	CORPORATE GUARANTOR	 		 		 	
				
	SIGNED by    

	 		 	)	 	 /s/ Eugenia Papapontikou

		 		 	)	 
	for and on behalf of	 		 	)	 
	DRYSHIPS INC.	 		 	)	 
	in the presence of:	 		 	)	 
				
	 /s/ Christoforos Bismpikos
 CHRISTOFOROS BISMPIKOS
 SOLICITOR
 WATSON, FARLEY & WILLIAMS
 89 AKTI MIAOULI
 PIRAEUS 18538 - GREECE
	 		 		 	
				
	LENDER	 		 		 	
				
	SIGNED by    

 	 		 	)	 	 /s/ Vassiliki Georgopoulos

		 		 	)	 
	for and on behalf of	 		 	)	 
	WESTLB AG, LONDON BRANCH	 		 	)	 
	in the presence of:	 		 	)	 
				
	 /s/ Christoforos Bismpikos
 CHRISTOFOROS BISMPIKOS
 SOLICITOR
 WATSON, FARLEY & WILLIAMS
 89 AKTI MIAOULI
 PIRAEUS 18538 - GREECE
	 		 		 	

  

 16

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