Document:

Offer letter of Robert Potter

 Exhibit 10.27 
 May 23, 2008 
 Robert Potter 
 2615 Ferndale Place NE 
 Renton WA 98056 
 Dear Rob: 
 In recognition of your achievements and dedication in helping to build our business, I
am very pleased to promote you to Vice President, Chief Accounting Officer effective May 29, 2008, reporting to me. 
 As Vice President,
Chief Accounting Officer, your new salary will be $200,000. In addition, you will be eligible to receive an annual target bonus of 35% of your annual salary, based on both company and individual performance. Depending on the level of company and
individual performance, you may receive between 0% and 125% of this target amount. Your bonus compensation for subsequent years will be determined by the Board of Directors and the CEO. Your compensation package will be reviewed annually.

 Please note that your employment continues to be at-will employment, which means that you have the right to terminate your employment at any
time with or without cause or notice, and the Company reserves for itself the same right. 
 Congratulations, I look forward to a continued
successful working relationship. Kindly indicate your consent to the terms of this offer letter by signing and returning a copy to Human Resources by May 30, 2008 
 Sincerely, 
  

	
	/s/
	
	Dawn Lepore
	President, CEO and Chairman

  

									
	Agreed and accepted:	 	 /s/
	 		  	Date:	  	 6/10/08

		 	 Robert PotterOffer letter of Tracy Wright

 Exhibit 10.28 
 May 23, 2008 
 Tracy Wright 
 4421 240th Pl SE 
 Bothell WA, 98021 
 Dear Tracy: 
 In recognition of your achievements and dedication in helping build our business, I
am very pleased to promote you to Vice President, Chief Finance Officer effective May 29, 2008, reporting to me. 
 As Vice President,
Chief Finance Officer, your new salary will be $200,000. In addition, you will be eligible to receive an annual target bonus of 35% of your annual salary, based on both company and individual performance. Depending on the level of company and
individual performance, you may receive between 0% and 125% of this target amount. Your bonus compensation for subsequent years will be determined by the Board of Directors and the CEO. Your compensation package will be reviewed annually.

 Please note that your employment continues to be at-will employment, which means that you have the right to terminate your employment at any
time with or without cause, and the Company reserves for itself the same right. 
 Congratulations, I look forward to a continued successful
working relationship. Kindly indicate your consent to the terms of this offer letter by signing and returning a copy to Human Resources by May 30, 2008  
 Sincerely, 
  

	
	/s/
	
	Dawn Lepore
	President, CEO and Chairman

  

									
	Agreed and accepted:	 	 /s/
	 		  	Date:	  	 6/30/08

		 	 Tracy WrightForm of Change in Control Agreement with Executive Officers

 Exhibit 10.29 
 DRUGSTORE.COM, INC. 
 CHANGE IN CONTROL AGREEMENT 

This Change in Control Agreement (the “Agreement”) is made and entered into by and between
                     (“Executive”) and drugstore.com, inc. (the “Company”), effective as of January 26, 2009 (the
“Effective Date”). 
 RECITALS 
 1. It is expected that the Company from time to time will consider the possibility of an acquisition by another company or other change in control. The Board of Directors of the Company (the
“Board”) recognizes that such consideration can be a distraction to Executive and can cause Executive to consider alternative employment opportunities. The Board has determined that it is in the best interests of the Company and its
stockholders to assure that the Company will have the continued dedication and objectivity of Executive, notwithstanding the possibility, threat or occurrence of a Change in Control (as defined herein) of the Company. 

2. The Board believes that it is in the best interests of the Company and its stockholders to provide Executive with an incentive to
continue his or her employment and to motivate Executive to maximize the value of the Company upon a Change in Control for the benefit of its stockholders. 
 3. The Board believes that it is imperative to provide Executive with certain severance benefits upon Executive’s termination of employment following a Change in Control. These benefits will provide
Executive with enhanced financial security and incentive and encouragement to remain with the Company notwithstanding the possibility of a Change in Control. 
 4. Certain capitalized terms used in the Agreement are defined in Section 6 below. 
 AGREEMENT 
 NOW, THEREFORE, in consideration of the mutual covenants
contained herein, the parties hereto agree as follows: 
 1. Term of Agreement. This Agreement will terminate upon the
date that all of the obligations of the parties hereto with respect to this Agreement have been satisfied. 
 2. At-Will
Employment. The Company and Executive acknowledge that Executive’s employment is and will continue to be at-will, as defined under applicable law. 

 3. Severance Benefits. 

(a) Involuntary Termination Following a Change in Control. If upon or within twelve (12) months following a Change in Control
(i) Executive terminates his or her employment with the Company (or any parent, subsidiary or successor of the Company) for Good Reason (as defined herein) or (ii) the Company (or any parent, subsidiary or successor of the Company)
terminates Executive’s employment without Cause (as defined herein), and Executive signs and does not revoke the release of claims as required by Section 4, Executive will receive the following severance benefits from the Company:

 (i) Severance Payment. Executive will receive a single lump sum severance payment (less applicable withholding taxes)
in an amount equal to twelve (12) months of Executive’s annual salary (the “Severance Period”) determined at a rate equal to the greater of (A) Executive’s annual salary as in effect immediately prior to the Change in
Control, or (B) Executive’s Base Salary (as defined herein).  
 (ii) Bonus Payment. Executive will
receive a lump sum cash payment (less applicable withholding taxes) in an amount equal to one hundred percent (100%) of Executive’s target annual incentive for the year of the Change in Control. 

(iii) Equity Awards. One hundred percent (100%) of Executive’s then outstanding and unvested Equity Awards as of the
date of Executive’s termination of employment will become vested and will otherwise remain subject to the terms and conditions of the applicable Equity Award agreement. 
 (iv) Benefits. The Company agrees to pay for health continuation coverage premiums for Executive at the same level of health coverage and benefits as in effect for on the day immediately preceding
the date of termination; provided, however, that (1) Executive constitutes a qualified beneficiary, as defined in Section 4980(B)(g)(1) of the Internal Revenue Code of 1986, as amended (the “Code”); and (2) Executive elects
continuation coverage pursuant to the Consolidated Omnibus Budget Reconciliation Act of 1985, as amended (“COBRA”), within the time period prescribed pursuant to COBRA. The Company will pay such COBRA premiums to provide for continuation
benefits on behalf of the Executive through the Severance Period. Executive will thereafter be responsible for the payment of COBRA premiums (including, without limitation, all administrative expenses) for the remaining COBRA period. 

(b) Timing of Severance Payments. Unless otherwise required pursuant to Section 10 of this Agreement, the Company will pay
the cash severance payments to which Executive is entitled under this Agreement in a lump sum as soon as practicable following the date of termination, provided, however, that such payment will be delayed to the extent required by Section 4
and/or Section 10 of this Agreement. Except to the extent payment is delayed pursuant to Section 9(b), all cash severance payments under this Agreement will be paid no later than March 15 of the year following the year in which the
termination occurs. 

  
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 (c) Voluntary Resignation; Termination For Cause. If Executive’s employment with
the Company terminates (i) voluntarily by Executive (other than for Good Reason) or (ii) for Cause by the Company, then Executive will not be entitled to receive severance or other benefits except for those (if any) as may then be
established under the Company’s then existing severance and benefits plans and practices or pursuant to other written agreements with the Company, including, without limitation, any Equity Award agreement. 

(d) Disability; Death. If the Company terminates Executive’s employment as a result of Executive’s Disability, or
Executive’s employment terminates due to his or her death, then Executive will not be entitled to receive severance or other benefits except for those (if any) as may then be established under the Company’s then existing written severance
and benefits plans and practices or pursuant to other written agreements with the Company, including, without limitation, any Equity Award agreement. 
 (e) Termination Apart from Change in Control. In the event Executive’s employment is terminated for any reason, either prior to the occurrence of a Change in Control or after the twelve
(12) month period following a Change in Control, then Executive will be entitled to receive severance and any other benefits only as may then be established under the Company’s existing written severance and benefits plans and practices or
pursuant to other written agreements with the Company, including, without limitation, any Equity Award agreement. 
 (f)
Exclusive Remedy. In the event of a termination of Executive’s employment upon or within twelve (12) months following a Change in Control, the provisions of this Section 3 are intended to be and are exclusive and in lieu of any
other rights or remedies to which Executive or the Company may otherwise be entitled, whether at law, tort or contract, in equity, or under this Agreement. Executive will be entitled to no benefits, compensation or other payments or rights upon
termination of employment following a Change in Control other than those benefits expressly set forth in this Section 3, except as may be provided in any Equity Award agreement. 

4. Conditions to Receipt of Severance. 

(a) Release of Claims Agreement. The receipt of any severance or other benefits pursuant to Section 3 will
be subject to Executive signing and not revoking a release of claims agreement in a form reasonably acceptable to the Company, and such release becoming effective and irrevocable within sixty (60) days of Executive’s termination or such
earlier deadline required by the release (such deadline, the “Release Deadline”). No severance or other benefits will be paid or provided until the release of claims agreement becomes effective and irrevocable, and any severance amounts or
benefits otherwise payable between the date of Executive’s termination and the date such release becomes effective shall be paid on the effective date of such release. Notwithstanding the foregoing, and subject to the release becoming effective
and irrevocable by the Release Deadline, any severance payments or benefits under this Agreement that would be considered Deferred Compensation Separation Benefits (as defined in Section 10(b)) shall be paid on the sixtieth (60th) day following Executive’s “separation from
service” within the meaning of Section 409A of the Code, or, if later, such time as required by Section 10(b). If the release does not become effective by the Release Deadline, Executive will forfeit all rights to severance payments
and benefits under this Agreement. 

  
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 (b) Other Requirement. Executive’s receipt of any payments or benefits under
Section 3 will be subject to Executive continuing to comply with the terms of any form of confidential information agreement. 
 (c) No Duty to Mitigate. Executive will not be required to mitigate the amount of any payment contemplated by this Agreement, nor will any earnings that Executive may receive from any other source
reduce any such payment. 
 5. Limitation on Payments. In the event that the severance and other benefits provided for in
this Agreement or otherwise payable to Executive (i) constitute “parachute payments” within the meaning of Section 280G of the Code and (ii) but for this Section 5, would be subject to the excise tax imposed by
Section 4999 of the Code, then Executive’s severance benefits under Section 3 will be either: 
  

	 	(a)	delivered in full, or 

  

	 	(b)	delivered as to such lesser extent which would result in no portion of such severance benefits being subject to excise tax under Section 4999 of the Code,

 whichever of the foregoing amounts, taking into account the applicable federal, state and local income taxes and the excise tax
imposed by Section 4999, results in the receipt by Executive on an after-tax basis, of the greatest amount of severance benefits, notwithstanding that all or some portion of such severance benefits may be taxable under Section 4999 of the
Code. Unless the Company and Executive otherwise agree in writing, any determination required under this Section 5 will be made in writing by the Company’s independent public accountants immediately prior to a Change in Control or a
“Big Four” national accounting firm selected by the Company (the “Accountants”), whose determination will be conclusive and binding upon Executive and the Company for all purposes. For purposes of making the calculations required
by this Section 5, the Accountants may make reasonable assumptions and approximations concerning applicable taxes and may rely on reasonable, good faith interpretations concerning the application of Sections 280G and 4999 of the Code. The
Company and Executive will furnish to the Accountants such information and documents as the Accountants may reasonably request in order to make a determination under this Section. The Company will bear all costs the Accountants may reasonably incur
in connection with any calculations contemplated by this Section 5. Any reduction in payments and/or benefits required by this Section 5 shall occur in the following order: (1) reduction of cash payments; (2) reduction of vesting
acceleration of Equity Awards; and (3) reduction of other benefits paid or provided to Executive. In the event that acceleration of vesting of Equity Awards is to be reduced, such acceleration of vesting shall be cancelled in the reverse order
of the date of grant for Executive’s Equity Awards. If two or more Equity Awards are granted on the same date, each Equity Award will be reduced on a pro-rata basis. In no event will Executive exercise any discretion with respect to the
ordering of any reduction of payments or benefits pursuant to this Section 5. 

  
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 6. Definition of Terms. The following terms referred to in this Agreement will have
the following meanings: 
 (a) Base Salary. For purposes of determining the severance payment under this Agreement,
“Base Salary” will mean Executive’s annual salary as in effect on the last day of the calendar year immediately prior to the year in which the Change in Control occurs. 

(b) Cause. For purposes of this Agreement, “Cause” will mean: 

(i) Any act of personal dishonesty taken by Executive in connection with Executive’s responsibilities as an employee [and intended
to result in substantial personal enrichment of Executive]; 
 (ii) Executive’s conviction of, or plea of nolo
contendere to, a felony; 
 (iii) Executive’s gross misconduct; 

(iv) Executive’s continued failure to perform the duties and responsibilities of Executive’s position after there has been
delivered to Executive a written demand for performance from the Company which describes the basis for the belief that Executive has not substantially performed such duties and responsibilities and that Executive has not corrected such failure
within two (2) weeks of such written demand. 
 (c) Change in Control. For purposes of this Agreement, “Change
in Control” shall have the same meaning as defined in the Company’s 2008 Equity Incentive Plan. 
 (d)
Disability. For purposes of this Agreement, “Disability” shall have the same meaning as that term is defined in the Company’s 2008 Equity Incentive Plan. Notwithstanding the foregoing however, should the Company maintain a
long-term disability plan at any time during Executive’s employment with the Company, a determination of Disability under such plan shall also be considered a “Disability” for purposes of this Agreement. 

(e) Good Reason. For purposes of this Agreement and any Equity Award agreement, “Good Reason” means the occurrence of
any of the following, without Executive’s express written consent: 
 (i) A material reduction of Executive’s
authority, duties or responsibilities; 
 (ii) A material reduction in Executive’s base compensation; 

(iii) A material change in the geographic location at which Executive must perform his or her services; provided that in no instance
will the relocation of Executive to a facility or a location of fifty (50) miles or less from Executive’s then current office location be deemed material for purposes of this Agreement; 

provided, however, that before Executive may resign for Good Reason, (A) Executive must provide the Company with written notice within ninety
(90) days of the initial event that Executive believes constitutes “Good Reason” specifically identifying the facts and circumstances claimed to constitute the grounds for Executive’s resignation for Good Reason and the proposed
termination date (which 

  
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will not be more than forty-five (45) days after the giving of written notice hereunder by Executive to the Company), and (B) the Company must have an opportunity of at least thirty
(30) days following delivery of such notice to cure the Good Reason condition and the Company must have failed to cure such Good Reason condition. 
 Executive specifically acknowledges and agrees that the definition of “Good Reason” in this Section 6(e) shall operate with respect to all rights to severance and/or accelerated vesting of
any Equity Award paid upon a termination upon or after a Change in Control and shall supersede and replace in its entirety any other definitions of “Good Reason,” “Involuntary Termination,” or other similar terms that may exist
in any other employment agreement, offer letter, severance plan or policy, Equity Award agreement or Company stock incentive plan document. 
 7. Successors. 
 (a) The Company’s Successors. Any successor to
the Company (whether direct or indirect and whether by purchase, merger, consolidation, liquidation or otherwise) to all or substantially all of the Company’s business and/or assets will assume the obligations under this Agreement and agree
expressly to perform the obligations under this Agreement in the same manner and to the same extent as the Company would be required to perform such obligations in the absence of a succession. For all purposes under this Agreement, the term
“Company” will include any successor to the Company’s business and/or assets which executes and delivers the assumption agreement described in this Section 7(a) or which becomes bound by the terms of this Agreement by operation
of law. 
 (b) Executive’s Successors. The terms of this Agreement and all rights of Executive hereunder will inure
to the benefit of, and be enforceable by, Executive’s personal or legal representatives, executors, administrators, successors, heirs, distributees, devisees and legatees. 

8. Notice. 
 (a) General. Notices and all other communications contemplated by this Agreement will be in writing and will be deemed to have been duly given when personally delivered or when mailed by U.S.
registered or certified mail, return receipt requested and postage prepaid. In the case of Executive, mailed notices will be addressed to him or her at the home address which he or she most recently communicated to the Company in writing. In the
case of the Company, mailed notices will be addressed to its corporate headquarters, and all notices will be directed to the attention of its President. 
 (b) Notice of Termination. Any termination by the Company for Cause or by Executive for Good Reason or as a result of a voluntary resignation will be communicated by a notice of termination to the
other party hereto given in accordance with Section 8(a) of this Agreement. Such notice will indicate the specific termination provision in this Agreement relied upon, will set forth in reasonable detail the facts and circumstances claimed to
provide a basis for termination under the provision so indicated, and will specify the termination date. The failure by Executive to include in the notice any fact or circumstance which contributes to a showing of Good Reason will not waive any
right of Executive hereunder or preclude Executive from asserting such fact or circumstance in enforcing his or her rights hereunder. 

  
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 9. Arbitration. The Company and Executive each agree that any and all disputes
arising out of the terms of this Agreement, Executive’s employment by the Company, Executive’s service as an officer or director of the Company, or Executive’s compensation and benefits, their interpretation and any of the matters
herein released, will be subject to binding arbitration. In the event of a dispute, the parties (or their legal representatives) will promptly confer to select a single arbitrator mutually acceptable to both parties. If the parties cannot agree on
an arbitrator, then the moving party may file a demand for arbitration with the Judicial Arbitration and Mediation Services (“JAMS”) in King County, Washington, who will be selected and appointed consistent with the Employment Arbitration
Rules and Procedures of JAMS (the “JAMS Rules”), except that such arbitrator must have the qualifications set forth in this paragraph. Any arbitration will be conducted in a manner consistent with the JAMS Rules, supplemented by the
Washington Rules of Civil Procedure. The parties further agree that the prevailing party in any arbitration will be entitled to injunctive relief in any court of competent jurisdiction to enforce the arbitration award. The parties hereby agree to
waive their right to have any dispute between them resolved in a court of law by a judge or jury. This paragraph will not prevent either party from seeking injunctive relief (or any other provisional remedy) from any court having jurisdiction
over the parties and the subject matter of their dispute relating to Executive’s obligations under this Agreement and the Company’s form of confidential information agreement. 

10. Code Section 409A. 
 (a) Any amount paid under this Agreement that satisfies the requirements of the “short-term deferral” rule set forth in Section 1.409A-1(b)(4) of the regulations issued under
Section 409A of the Code (the “Treasury Regulations”) shall not constitute Deferred Compensation Separation Benefits for purposes of Section 10(b) below, and consequently shall be paid to Executive promptly following termination
as required by Section 3 of this Agreement. It is intended that all cash severance payments under this Agreement, if any, satisfy the short-term deferral rule. 
 (b) Notwithstanding anything to the contrary in this Agreement, no Deferred Compensation Separation Benefits (as defined in this Section 10(b)) will become payable under this Agreement until
Executive has a “separation from service” within the meaning of Section 409A of the Code, and any proposed or final regulations and guidance promulgated thereunder (“Section 409A”). Further, if Executive is a “specified
employee” within the meaning of Section 409A at the time of Executive’s separation from service (other than due to Executive’s death), and the severance payable to Executive, if any, pursuant to this Agreement, when considered
together with any other severance payments or separation benefits, are considered deferred compensation under Section 409A (together, the “Deferred Compensation Separation Benefits”), such Deferred Compensation Separation Payments
that are otherwise payable within the first six (6) months following Executive’s termination of employment will become payable on the first payroll date that occurs on or after the date six (6) months and one (1) day following
the date of Executive’s separation from service. All subsequent Deferred Compensation Separation Benefits, if any, will be payable in accordance with the payment schedule applicable to each payment or benefit. Notwithstanding anything herein to
the contrary, if Executive dies following his or her separation from service but prior to the six (6) month 

  
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anniversary of his or her separation from service, then any payments delayed in accordance with this paragraph will be payable in a lump sum as soon as administratively practicable after the date
of Executive’s death and all other Deferred Compensation Separation Benefits will be payable in accordance with the payment schedule applicable to each payment or benefit. Each payment and benefit payable under this Agreement is intended to
constitute a separate payment for purposes of Section 1.409A-2(b)(2) of the Treasury Regulations. 
 (c) Any amount paid
under this Agreement that qualifies as a payment made as a result of an involuntary separation from service pursuant to Section 1.409A-1(b)(9)(iii) of the Treasury Regulations that does not exceed the Section 409A Limit (as defined below)
shall not constitute Deferred Compensation Separation Benefits for purposes of Section 10(b) above. For purposes of this Section 10(c), “Section 409A Limit” will mean two (2) times the lesser of: (i) Executive’s
annualized compensation based upon the annual rate of pay paid to Executive during Executive’s taxable year preceding the Executive’s taxable year of Executive’s separation from service as determined under Treasury Regulation
1.409A-1(b)(9)(iii)(A)(1); or (ii) the maximum amount that may be taken into account under a qualified plan pursuant to Section 401(a)(17) of the Code for the year in which Executive’s separation from service occurs. 

(d) The foregoing provisions are intended to comply with the requirements of Section 409A so that none of the severance payments and
benefits to be provided hereunder will be subject to the additional tax imposed under Section 409A, and any ambiguities herein will be interpreted to so comply. The Company and Executive agree to work together in good faith to consider
amendments to this Agreement and to take such reasonable actions which are necessary, appropriate or desirable to avoid imposition of any additional tax or income recognition prior to actual payment to Executive under Section 409A. 

11. Miscellaneous Provisions. 
 (a) Waiver. No provision of this Agreement will be modified, waived or discharged unless the modification, waiver or discharge is agreed to in writing and signed by Executive and by an authorized
officer of the Company (other than Executive). No waiver by either party of any breach of, or of compliance with, any condition or provision of this Agreement by the other party will be considered a waiver of any other condition or provision or of
the same condition or provision at another time. 
 (b) Headings. All captions and section headings used in this
Agreement are for convenient reference only and do not form a part of this Agreement. 
 (c) Choice of Law. The validity,
interpretation, construction and performance of this Agreement will be governed by the laws of the State of Washington (with the exception of its conflict of laws provisions). 
 (d) Integration. This Agreement, together with the form of confidential information agreement and the standard forms of Equity Award agreement that describe Executive’s outstanding Equity
Awards (other than as such Equity Award agreements have been revised pursuant to this Agreement), represents the entire agreement and understanding between the parties 

  
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as to the subject matter herein and supersedes all prior or contemporaneous agreements whether written or oral. With respect to Equity Awards granted on or after the date of this Agreement, the
acceleration of vesting provisions provided herein will apply to such Equity Awards except to the extent otherwise explicitly provided in the applicable Equity Award agreement. No waiver, alteration, or modification of any of the provisions of this
Agreement will be binding unless in a writing and signed by duly authorized representatives of the parties hereto. In entering into this Agreement, no party has relied on or made any representation, warranty, inducement, promise, or understanding
that is not in this Agreement. To the extent that any provisions of this Agreement conflict with those of any other agreement between the Executive and the Company, the terms in this Agreement will prevail. 

(e) Severability. In the event that any provision or any portion of any provision hereof becomes or is declared by a court of
competent jurisdiction to be illegal, unenforceable, or void, this Agreement will continue in full force and effect without said provision or portion of provision. The remainder of this Agreement shall be interpreted so as best to effect the intent
of the Company and Executive. 
 (f) Withholding. All payments made pursuant to this Agreement will be subject to
withholding of applicable income and employment taxes. 
 (g) Counterparts. This Agreement may be executed in
counterparts, each of which will be deemed an original, but all of which together will constitute one and the same instrument. 

  
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 IN WITNESS WHEREOF, each of the parties has executed this Agreement, in the case of the
Company by its duly authorized officer, as of the day and year set forth below. 
 Executive understands and acknowledges that
the definition of “Good Reason” contained in this Agreement shall supersede any and all such similar definitions contained in employment agreements, offer letters, severance policies and plans and Equity Award agreements to the extent such
other agreements provide for benefits contingent on a Change in Control, and that by executing this Agreement, Executive acknowledges such other arrangements have been amended accordingly. 

 

							
	COMPANY	 		 	DRUGSTORE.COM, INC.
				
		 		 	By:	 	  

		 		 		 	Dawn Lepore,
		 		 		 	President and Chief Executive Officer
				
	EXECUTIVE	 		 	By:	 	  

				
		 		 	Title:	 	  

  
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