1006-00008 · Crestline Packaging Solutions LLC · Closing

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CALDERWOOD & HARKNESS LLP Attorneys at Law

425 Lexington Avenue, 31st Floor New York, New York 10017

Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com

August 15, 2025

Ironclad National Bank, as Administrative Agent 301 South Tryon Street Charlotte, North Carolina 28202

Attention: Kenneth Boateng, Senior Vice President, Healthcare & Specialty Lending

Re: Amendment No. 3 to Credit Agreement dated September 17, 2021 (as amended) among Crestline Packaging Solutions LLC, CPS Holdings, Inc., the Lenders party thereto, and Ironclad National Bank, as Administrative Agent — Incremental Term Loan in the aggregate principal amount of $84,000,000

Ladies and Gentlemen:

I. Introduction

We have acted as counsel to Crestline Packaging Solutions LLC, a Delaware limited liability company ("Crestline" or the "Borrower"), and CPS Holdings, Inc., a Delaware corporation ("Holdings" and, together with the Borrower, the "Credit Parties"), in connection with (a) Amendment No. 3 ("Amendment No. 3") to the Credit Agreement dated as of September 17, 2021 (as amended by Amendment No. 1 dated March 22, 2023, Amendment No. 2 dated November 8, 2024, and as further amended, restated, supplemented, or otherwise modified from time to time, the "Credit Agreement"), among the Borrower, Holdings, the Lenders party thereto from time to time (the "Lenders"), and Ironclad National Bank, as administrative agent for the Lenders (in such capacity, the "Administrative Agent"), and (b) the incurrence of an incremental term loan in the aggregate principal amount of Eighty-Four Million Dollars ($84,000,000) (the "Incremental Term Loan") thereunder. Amendment No. 3 and the Credit Agreement are hereinafter referred to together with the other documents, instruments, and agreements executed and delivered in connection therewith (including the Amended and Restated Security Agreement, the Amended and Restated Guaranty Agreement, and the other Collateral Documents, each as defined in the Credit Agreement) as the "Financing Documents."

This opinion letter is delivered to you pursuant to Section 5.01(h) of Amendment No. 3 to the Credit Agreement as a condition precedent to the effectiveness thereof and the funding of the Incremental Term Loan on the date hereof (the "Closing Date"). Capitalized terms used but not otherwise defined herein shall have the meanings assigned to them in the Credit Agreement, as amended by Amendment No. 3.

II. Documents Examined

In rendering the opinions expressed herein, we have examined originals or copies, certified or otherwise identified to our satisfaction, of the following documents:

1. Amendment No. 3 to the Credit Agreement, dated as of the date hereof, among the Borrower, Holdings, the Lenders party thereto, and the Administrative Agent (the "Amendment");

2. The Credit Agreement dated as of September 17, 2021, among the Borrower, Holdings, the Lenders party thereto from time to time, and the Administrative Agent, as amended by Amendment No. 1 dated as of March 22, 2023, and Amendment No. 2 dated as of November 8, 2024;

3. The Incremental Term Loan Assumption Agreement executed by the Incremental Term Loan Lenders, dated as of the date hereof, together with the related Lender Joinder Agreements;

4. The Amended and Restated Security Agreement, dated as of the date hereof, among the Credit Parties and the Administrative Agent, for the benefit of the Secured Parties;

5. The Amended and Restated Guaranty Agreement, dated as of the date hereof, executed by Holdings in favor of the Administrative Agent, for the benefit of the Secured Parties;

6. The related Collateral Documents, including the Pledge Agreements, IP Security Agreements, and Deposit Account Control Agreements executed and delivered in connection with the Financing Documents;

7. The Asset Purchase Agreement, dated as of June 16, 2025 (the "APA"), by and among the Borrower, Lakewood Regional Health Partners, LLC ("Lakewood"), Dr. Raymond Alcott, and Dr. Nadia Petrosian, together with all schedules, exhibits, disclosure schedules, and ancillary documents thereto;

8. The Certificate of Formation of Crestline Packaging Solutions LLC, as filed with the Secretary of State of the State of Delaware on July 14, 2020, together with all amendments thereto, as certified by the Secretary of Crestline;

9. The Limited Liability Company Agreement of Crestline Packaging Solutions LLC, dated as of July 14, 2020, as amended to date (the "LLC Agreement"), as certified by the Secretary of Crestline;

10. The Certificate of Incorporation of CPS Holdings, Inc., as filed with the Secretary of State of the State of Delaware on June 29, 2020, together with all amendments thereto, as certified by the Secretary of CPS Holdings;

11. The Bylaws of CPS Holdings, Inc., as amended to date, as certified by the Secretary of CPS Holdings;

12. A Certificate of Good Standing for Crestline Packaging Solutions LLC issued by the Secretary of State of the State of Delaware, dated August 12, 2025;

13. A Certificate of Good Standing for CPS Holdings, Inc. issued by the Secretary of State of the State of Delaware, dated August 12, 2025;

14. Written consent of Pinnacle River GP IV, LLC, as the sole managing member of Crestline, dated as of August 14, 2025, approving and authorizing the execution, delivery, and performance by Crestline of the APA, Amendment No. 3, and the other Transaction Documents and Financing Documents to which Crestline is a party, and the consummation of the transactions contemplated thereby, including the incurrence of the Incremental Term Loan;

15. Resolutions of the Board of Directors of CPS Holdings, Inc., adopted by unanimous written consent dated as of August 14, 2025, authorizing the execution, delivery, and performance by CPS Holdings of each of the Financing Documents to which it is a party, including the Amended and Restated Guaranty Agreement, and the consummation of the transactions contemplated thereby;

16. An Officer's Certificate of Crestline Packaging Solutions LLC, dated as of the date hereof, executed by an authorized officer of Crestline, certifying as to, among other things, the incumbency and specimen signatures of the officers executing the Financing Documents and the APA on behalf of Crestline, the accuracy of the organizational documents of Crestline, and the satisfaction of certain conditions precedent set forth in Amendment No. 3;

17. An Officer's Certificate of CPS Holdings, Inc., dated as of the date hereof, executed by an authorized officer of CPS Holdings, certifying as to, among other things, the incumbency and specimen signatures of the officers executing the Financing Documents on behalf of CPS Holdings, the accuracy of the organizational documents of CPS Holdings, and the satisfaction of certain conditions precedent set forth in Amendment No. 3; and

18. Such other certificates, documents, instruments, corporate and limited liability company records, agreements, and other materials as we have deemed necessary or appropriate for the purposes of the opinions expressed herein.

In addition, we have reviewed such questions of law as we have considered necessary or appropriate for the purposes of the opinions expressed herein. We have also made such inquiries of officers and representatives of the Credit Parties as we have deemed relevant, and we have obtained and relied upon such certificates and assurances from officers and representatives of the Credit Parties and from public officials as we have deemed necessary or appropriate as a basis for the opinions set forth below.

III. Assumptions

In rendering the opinions set forth below, we have assumed, without independent investigation or verification, the following:

(a) The genuineness of all signatures on all documents examined by us, other than the signatures of officers and authorized representatives of the Credit Parties.

(b) The authenticity of all documents submitted to us as originals, the conformity to the originals of all documents submitted to us as copies (whether certified, photostatic, electronic, or otherwise), and the authenticity of the originals of such copies.

(c) The legal capacity of all natural persons who have executed any of the documents reviewed by us in connection with the rendering of this opinion.

(d) That each party to the Financing Documents (other than the Credit Parties) has been duly organized or formed, is validly existing and in good standing under the laws of its jurisdiction of organization or formation, and has all requisite power and authority to execute, deliver, and perform its obligations under each Financing Document to which it is a party.

(e) That Amendment No. 3, the Credit Agreement, and each of the other Financing Documents constitute the legal, valid, and binding obligations of each party thereto (other than the Credit Parties), enforceable against each such party in accordance with their respective terms.

(f) The accuracy and completeness of all factual matters set forth in all certificates, representations, and statements of fact furnished to us by officers and representatives of the Credit Parties, including the Officer's Certificates delivered on the date hereof, and that all such certificates, representations, and statements remain true and correct as of the date hereof. We have not undertaken any independent investigation to verify the accuracy or completeness of any such factual matters.

(g) That there has been no mutual mistake of fact or misunderstanding, fraud, duress, undue influence, or other irregularity with respect to the negotiation, execution, or delivery of any of the Financing Documents or the APA.

(h) That the conduct of the parties to the Financing Documents has complied and will comply with any requirement of good faith, fair dealing, and conscionability applicable thereto.

(i) That the Administrative Agent and the Lenders have acted in good faith, without notice of any defense against the enforcement of any rights created by, or any defect in or objection to the validity or enforceability of, any of the Financing Documents, and without notice of any facts that would give rise to a personal defense of any party to any of the Financing Documents.

(j) That the Credit Agreement, as amended by Amendment No. 3, accurately reflects the complete agreement of the parties thereto with respect to the matters set forth therein, and that there are no oral or written agreements, understandings, or courses of dealing between the parties that would modify, amend, or supplement the terms of the Credit Agreement as so amended.

IV. Opinions

Based upon the foregoing, and subject to the assumptions, qualifications, limitations, and exceptions set forth herein, we are of the opinion that:

Opinion 1 — Due Organization and Good Standing of Crestline. Crestline Packaging Solutions LLC is a limited liability company duly formed, validly existing, and in good standing under the laws of the State of Delaware. In rendering this opinion, we have relied exclusively upon the Certificate of Good Standing issued by the Secretary of State of the State of Delaware dated August 12, 2025, the Certificate of Formation of Crestline (as certified to us), and the Officer's Certificate of Crestline delivered on the date hereof.

Opinion 2 — Due Organization and Good Standing of CPS Holdings. CPS Holdings, Inc. is a corporation duly incorporated, validly existing, and in good standing under the laws of the State of Delaware. In rendering this opinion, we have relied exclusively upon the Certificate of Good Standing issued by the Secretary of State of the State of Delaware dated August 12, 2025, the Certificate of Incorporation of CPS Holdings (as certified to us), and the Officer's Certificate of CPS Holdings delivered on the date hereof.

Opinion 3 — Power and Authority of Crestline. Crestline has the limited liability company power and authority to (a) own, lease, and operate its properties and assets and to carry on its business as presently conducted, (b) execute, deliver, and perform its obligations under each of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and (c) consummate the transactions contemplated thereby, including the acquisition of the Purchased Assets (as defined in the APA) from Lakewood Regional Health Partners, LLC, Dr. Raymond Alcott, and Dr. Nadia Petrosian and the incurrence of the Incremental Term Loan in the aggregate principal amount of Eighty-Four Million Dollars ($84,000,000).

Opinion 4 — Power and Authority of CPS Holdings. CPS Holdings, Inc. has the corporate power and authority to execute, deliver, and perform its obligations under each of the Financing Documents to which it is a party, including, without limitation, the Amended and Restated Guaranty Agreement, and to consummate the transactions contemplated thereby.

Opinion 5 — Due Authorization — Crestline. The execution, delivery, and performance by Crestline of the APA, Amendment No. 3, and each other Financing Document to which it is a party, and the consummation of the transactions contemplated thereby (including the acquisition of the Purchased Assets and the incurrence of the Incremental Term Loan), have been duly authorized by all necessary limited liability company action on the part of Crestline. Such authorization includes the written consent of Pinnacle River GP IV, LLC, as the sole managing member of Crestline, dated August 14, 2025, which consent was duly adopted in accordance with the LLC Agreement and the Delaware Limited Liability Company Act, 6 Del. C. § 18-101 et seq. No further approval, consent, or authorization of any member, manager, or other person or entity is required for the valid execution, delivery, and performance by Crestline of such documents or the consummation of such transactions.

Opinion 6 — Due Authorization — CPS Holdings. The execution, delivery, and performance by CPS Holdings of each Financing Document to which it is a party, and the consummation of the transactions contemplated thereby, have been duly authorized by all necessary corporate action on the part of CPS Holdings, including the unanimous written consent of the Board of Directors of CPS Holdings dated August 14, 2025. No stockholder approval is required under the Delaware General Corporation Law, the Certificate of Incorporation, or the Bylaws of CPS Holdings for the execution, delivery, and performance of any such Financing Document or the consummation of any such transactions.

Opinion 7 — Execution and Delivery. Each of the APA, Amendment No. 3, and the other Financing Documents to which any Credit Party is a party has been duly executed and delivered by such Credit Party. The persons who executed such documents on behalf of each Credit Party were, at the time of such execution, duly authorized to do so.

Opinion 8 — Enforceability. Each of the APA, Amendment No. 3, and the other Financing Documents to which any Credit Party is a party constitutes the legal, valid, and binding obligation of such Credit Party, enforceable against such Credit Party in accordance with its respective terms, subject, however, to the Enforceability Qualifications set forth in Section VI(A) below.

Opinion 9 — No Conflicts — Organizational Documents. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby (including the acquisition of the Purchased Assets and the incurrence of the Incremental Term Loan), do not and will not (a) violate, conflict with, or result in a breach of any provision of the Certificate of Formation or the Limited Liability Company Agreement of Crestline Packaging Solutions LLC, or (b) violate, conflict with, or result in a breach of any provision of the Certificate of Incorporation or Bylaws of CPS Holdings, Inc.

Opinion 10 — No Conflicts — Laws. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby (including the acquisition of the Purchased Assets and the incurrence of the Incremental Term Loan), do not and will not violate any law, statute, rule, or regulation of the State of New York, the State of Delaware, or the federal laws of the United States of America that, in our experience, are normally applicable to transactions of this type and that we, in the exercise of customary professional diligence, would reasonably recognize as being applicable to the Credit Parties or the transactions contemplated by the Financing Documents (collectively, the "Opined-Upon Laws"). We express no opinion with respect to any laws, statutes, rules, or regulations other than the Opined-Upon Laws, and we note in particular that this opinion does not address the healthcare regulatory laws, licensure requirements, certificate-of-need laws, or similar regulatory frameworks of any jurisdiction, including the State of New York and the Commonwealth of Pennsylvania, as discussed in Section VI(C) below.

Opinion 11 — No Conflicts — Orders and Judgments. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby, do not and will not, to our knowledge (as defined in Section V below, and based solely on inquiry of Derek Okonkwo and Tiffany Rosenthal, each of whom has had primary responsibility for representing the Credit Parties in connection with this matter), violate any order, judgment, injunction, writ, or decree of any court or governmental authority binding upon any Credit Party or any of its properties or assets.

Opinion 12 — No Conflicts — Material Agreements. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby, do not and will not result in a breach of, constitute a default (or an event that, with the giving of notice or lapse of time, or both, would constitute a default) under, require any consent not already obtained under, or give rise to any right of termination, cancellation, acceleration, or loss of any material benefit under, any of the material agreements, contracts, and instruments listed on Schedule I hereto (collectively, the "Reviewed Agreements"), except where such breach, default, or right would not reasonably be expected to have a Material Adverse Effect (as defined in the Credit Agreement). Our opinion in this paragraph is limited solely to the Reviewed Agreements listed on Schedule I and does not extend to any other agreement, contract, instrument, or arrangement to which any Credit Party may be a party or by which any Credit Party or its properties or assets may be bound.

Opinion 13 — Governmental Approvals. No consent, approval, authorization, order, license, permit, registration, qualification, or filing with any federal, state, or local governmental authority under the Opined-Upon Laws is required for the execution, delivery, and performance by any Credit Party of Amendment No. 3 or the other Financing Documents to which it is a party, or for the incurrence of the Incremental Term Loan, except for (a) those consents, approvals, authorizations, orders, registrations, qualifications, and filings that have been obtained or made on or prior to the date hereof and are in full force and effect as of the date hereof, (b) the filing of UCC-1 financing statements (and continuation statements in connection therewith) in the office of the Secretary of State of the State of Delaware (with respect to each of Crestline and CPS Holdings, as debtors organized in Delaware) and in such other filing offices as may be necessary or appropriate to perfect the security interests created by the Collateral Documents, and (c) the approvals of the New York State Department of Health and the Pennsylvania Department of Health with respect to the change-of-ownership and operation of the clinical facilities being acquired pursuant to the APA, which approvals are conditions to Closing under the APA and are not required for the effectiveness of Amendment No. 3 or the incurrence of the Incremental Term Loan on the date hereof.

Opinion 14 — Security Interest (UCC). Amendment No. 3 and the Amended and Restated Security Agreement are effective to create in favor of the Administrative Agent, for the benefit of the Secured Parties, a valid security interest in all right, title, and interest of each of the Credit Parties in the Collateral described in the Amended and Restated Security Agreement, to the extent that Article 9 of the Uniform Commercial Code as in effect in the State of New York (the "NY UCC") is applicable to the creation of such security interest. Upon the filing of duly completed UCC-1 financing statements, in proper form for filing under Article 9 of the NY UCC, in the office of the Secretary of State of the State of Delaware (with respect to each of Crestline Packaging Solutions LLC and CPS Holdings, Inc., each as a debtor organized in the State of Delaware), such security interest will be perfected to the extent that a security interest in such Collateral may be perfected by the filing of a financing statement under the NY UCC. We express no opinion as to the perfection of any security interest in any Collateral consisting of (i) deposit accounts (which require control for perfection under Section 9-314 of the NY UCC), (ii) letter-of-credit rights (which require control for perfection under Section 9-314 of the NY UCC), (iii) electronic chattel paper (which requires control for perfection under Section 9-105 of the NY UCC), (iv) assets subject to a federal statute, regulation, or treaty that preempts Article 9 of the NY UCC, (v) real property or fixtures, or (vi) motor vehicles or other property subject to certificate-of-title statutes. We express no opinion as to the priority of any security interest.

Opinion 15 — Investment Company Act. Neither Crestline Packaging Solutions LLC nor CPS Holdings, Inc. is, or upon the consummation of the transactions contemplated by Amendment No. 3 and the other Financing Documents will be required to be, registered as an "investment company" within the meaning of the Investment Company Act of 1940, as amended.

V. Certain Additional Matters — Knowledge Qualifications

As used in this opinion letter, the phrases "to our knowledge," "known to us," and similar phrases with respect to matters of fact mean the actual knowledge, as of the date hereof and without independent investigation, of James Prentice, Sandra Tung, Derek Okonkwo, and Tiffany Rosenthal, each of whom is an attorney at this firm and has had substantive involvement in the representation of the Credit Parties in connection with the transactions described herein. We have not conducted any independent investigation or inquiry for the purpose of this opinion letter beyond the examination of the documents identified in Section II above and the inquiries described therein. No inference as to our knowledge of any fact or matter should be drawn from the absence of a knowledge qualification in any other opinion expressed herein.

VI. Qualifications and Limitations

The opinions set forth herein are subject to the following qualifications and limitations:

A. Enforceability Qualifications

The opinions expressed herein regarding the enforceability of the Financing Documents, the APA, and any other document or instrument are subject to and limited by:

(i) The effect of applicable bankruptcy, insolvency, reorganization, receivership, moratorium, fraudulent conveyance, fraudulent transfer, preferential transfer, and other similar laws now or hereafter in effect relating to or affecting creditors' rights and remedies generally, including, without limitation, the United States Bankruptcy Code (Title 11 of the United States Code) and the laws of the State of New York relating to fraudulent conveyances and transfers (Article 10 of the New York Debtor and Creditor Law);

(ii) The effect of general principles of equity, whether applied in a proceeding in equity or at law (including, without limitation, concepts of materiality, reasonableness, good faith, and fair dealing), and the discretionary nature of equitable remedies (including, without limitation, the remedies of specific performance and injunctive relief), regardless of whether enforceability is considered in a proceeding in equity or at law;

(iii) The qualification that certain provisions of the Financing Documents may be unenforceable in whole or in part under applicable law, but such unenforceability does not, in our opinion, render the Financing Documents invalid as a whole, and there exist in the Financing Documents or are otherwise available at law or in equity adequate remedies for the practical realization of the principal benefits intended to be provided thereby;

(iv) Limitations that may be imposed by law on the enforceability of provisions in the Financing Documents relating to indemnification, contribution, and exculpation to the extent that such provisions may contravene applicable law or public policy, including, without limitation, federal and state securities laws; and

(v) The effect of judicial decisions that may permit the introduction of extrinsic evidence to modify the terms or the interpretation of the Financing Documents.

The qualifications set forth in clauses (i) through (v) above are collectively referred to herein as the "Enforceability Qualifications."

B. Law Covered

The opinions expressed herein are limited in all respects to the laws of the State of New York (excluding the choice-of-law rules thereof, except as set forth in Section VI(D) below), the General Corporation Law of the State of Delaware (Title 8, Chapter 1 of the Delaware Code), the Limited Liability Company Act of the State of Delaware (Title 6, Chapter 18 of the Delaware Code), and the federal laws of the United States of America, in each case as currently in effect on the date hereof. We express no opinion as to the laws of any other jurisdiction, and we assume no obligation to advise you of any changes in law after the date hereof. Without limiting the generality of the foregoing, we express no opinion as to the healthcare regulatory laws, licensure requirements, certificate-of-need requirements, change-of-ownership regulations, Medicare or Medicaid participation requirements, or any other healthcare-related regulatory requirements of the State of New York, the Commonwealth of Pennsylvania, or any other jurisdiction. We understand that such matters have been separately addressed by Marchand Healthcare Regulatory Advisors, LLC in a separate opinion letter delivered to the Administrative Agent on or about the date hereof. In addition, we express no opinion with respect to any state or local tax laws or regulations.

C. No Opinion on Certain Matters

Without limiting the generality of Section VI(B) above, we express no opinion as to:

(i) The compliance by any Credit Party with, or the effect of, any financial covenants, financial tests, financial ratios, or other financial requirements set forth in the Credit Agreement, Amendment No. 3, or any other Financing Document, including, without limitation, the Consolidated Leverage Ratio, the Consolidated Interest Coverage Ratio, the Minimum Liquidity Covenant, or any pro forma financial tests required in connection with the incurrence of the Incremental Term Loan;

(ii) The effect of any future changes in applicable law, regulation, or administrative practice occurring after the date hereof;

(iii) The title of any Credit Party to any real or personal property, or the priority of any lien, security interest, mortgage, pledge, or other encumbrance, except as expressly set forth in Opinion 14 above;

(iv) Federal or state antitrust or competition laws, including, without limitation, the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended;

(v) Federal, state, or local environmental laws, regulations, or standards, including, without limitation, the Comprehensive Environmental Response, Compensation, and Liability Act, the Resource Conservation and Recovery Act, and any state equivalents thereof;

(vi) The Employee Retirement Income Security Act of 1974, as amended ("ERISA"), or any other federal, state, or local law relating to employee benefit plans, pension plans, or welfare benefit plans, or any matters arising thereunder;

(vii) Federal, state, or local tax laws or regulations, including, without limitation, the Internal Revenue Code of 1986, as amended, and any state or local tax codes;

(viii) Laws, rules, and regulations of the Federal Drug Enforcement Administration, the federal Controlled Substances Act, or any state controlled substance regulations;

(ix) Federal or state healthcare fraud and abuse laws, the Physician Self-Referral Law (commonly known as the "Stark Law"), 42 U.S.C. § 1395nn, the Federal Anti-Kickback Statute, 42 U.S.C. § 1320a-7b(b), the False Claims Act, 31 U.S.C. §§ 3729–3733, the Health Insurance Portability and Accountability Act of 1996 ("HIPAA"), the Health Information Technology for Economic and Clinical Health Act (the "HITECH Act"), or any state equivalents of any of the foregoing; and

(x) Federal, state, or local laws relating to intellectual property, including, without limitation, patent, trademark, copyright, and trade secret laws.

D. Additional Customary Qualifications

In addition to the Enforceability Qualifications and the other qualifications and limitations set forth above, the opinions expressed herein are subject to the following additional customary qualifications:

(i) Provisions of the Financing Documents that purport to establish evidentiary standards, or that purport to make determinations conclusive, may be limited or rendered unenforceable by applicable law.

(ii) Provisions of the Financing Documents that purport to constitute a waiver of rights or defenses, including, without limitation, waivers of the right to a jury trial, waivers of objections to venue, waivers of rights to assert counterclaims or setoffs, waivers of statutes of limitations, and similar waivers, may be limited or rendered unenforceable by applicable law.

(iii) While we express no opinion as to the enforceability of the choice-of-law provisions of the Financing Documents in all circumstances under New York conflicts-of-law principles, we note that, under Section 5-1401 of the New York General Obligations Law, a New York court should give effect to the selection of New York law set forth in the Financing Documents, provided the transaction bears a reasonable relation to the State of New York or involves an aggregate consideration of not less than $250,000, and we believe that such conditions are satisfied in the case of the Financing Documents.

(iv) We express no opinion that any guarantee provided by Holdings under the Amended and Restated Guaranty Agreement constitutes a "guaranty of payment" rather than a "guaranty of collection," except to the extent expressly provided in the terms of the Amended and Restated Guaranty Agreement itself. The characterization of any guarantee as absolute and unconditional may be subject to judicial interpretation.

(v) We express no opinion as to the enforceability of any provision of the Financing Documents that purports to grant any power of attorney to the extent that such grant may be revocable under applicable law.

(vi) We express no opinion as to the enforceability of any provision of the Financing Documents to the extent it purports to waive or limit the effect of applicable law governing the time within which suit must be commenced under any statute of limitations.

VII. Reliance and Distribution

This opinion letter is rendered solely for the benefit of the Administrative Agent and the Lenders under the Credit Agreement as of the date hereof, in their respective capacities as such, and solely in connection with the transactions contemplated by Amendment No. 3 and the incurrence of the Incremental Term Loan. This opinion letter may not be relied upon by any other person or entity, or for any other purpose, without our prior written consent. This opinion letter may not be quoted or referred to in any public document, public filing, or registration statement, or furnished to any other person or entity, without our prior written consent.

Notwithstanding the foregoing, this opinion letter may be disclosed to (a) prospective assignees and participants in the Incremental Term Loan and the other Loans and Commitments under the Credit Agreement, in accordance with the terms and conditions of the Credit Agreement (including Section 10.06 thereof), provided that such prospective assignees and participants are informed that (i) this opinion letter speaks only as of its date, (ii) such persons may not rely on this opinion letter without our prior written consent, and (iii) we undertake no obligation to update or supplement this opinion letter for the benefit of any such person; and (b) bank examiners, auditors, and regulatory authorities having jurisdiction over the Administrative Agent or any Lender, provided such disclosure is required by applicable law or regulation and such persons are informed that they may not rely on this opinion letter.

This opinion letter is rendered as of the date hereof, and we express no opinion as to facts, events, transactions, changes in law, or changes in circumstances occurring after the date hereof. We undertake no obligation, and hereby disclaim any obligation, to update or supplement this opinion letter, or to advise you or any other person of any changes in law or fact that may come to our attention after the date hereof, whether or not such changes would affect the opinions expressed herein.

VIII. Governing Law of Opinion Letter

This opinion letter shall be governed by, and construed in accordance with, the laws of the State of New York (without regard to the conflicts-of-law principles thereof, other than Section 5-1401 of the New York General Obligations Law).

[Remainder of page intentionally left blank; signature page follows.]

Very truly yours,

CALDERWOOD & HARKNESS LLP

By: ________

James Prentice, Partner

C&H Matter No. 1006-00008

JPrentice/STung/DOkonkwo/TRosenthal Enclosure: Schedule I

SCHEDULE I

Reviewed Agreements

(Referenced in Opinion 12)

The following is the list of material agreements, contracts, and instruments reviewed by Calderwood & Harkness LLP in connection with the no-conflicts opinion set forth in Opinion 12 of this opinion letter (collectively, the "Reviewed Agreements"):

1. Credit Agreement dated as of September 17, 2021, among Crestline Packaging Solutions LLC, CPS Holdings, Inc., the Lenders party thereto from time to time, and Ironclad National Bank, as Administrative Agent, as amended by Amendment No. 1 dated as of March 22, 2023, Amendment No. 2 dated as of November 8, 2024, and Amendment No. 3 dated as of the date hereof.

2. Amended and Restated Security Agreement, dated as of August 15, 2025, among Crestline Packaging Solutions LLC, CPS Holdings, Inc., and Ironclad National Bank, as Administrative Agent, for the benefit of the Secured Parties.

3. Amended and Restated Guaranty Agreement, dated as of August 15, 2025, executed by CPS Holdings, Inc. in favor of Ironclad National Bank, as Administrative Agent, for the benefit of the Secured Parties.

4. Asset Purchase Agreement, dated as of June 16, 2025, by and among Crestline Packaging Solutions LLC, Lakewood Regional Health Partners, LLC, Dr. Raymond Alcott, and Dr. Nadia Petrosian, together with all exhibits, schedules, and disclosure schedules thereto.

5. Escrow Agreement, dated as of August 15, 2025, among Crestline Packaging Solutions LLC, Lakewood Regional Health Partners, LLC, and Apex Title & Escrow Services, LLC, as escrow agent, with respect to (a) the Indemnification Escrow in the amount of $35,000,000 and (b) the Purchase Price Adjustment Escrow in the amount of $3,500,000.

6. Clearpath Health Systems, Inc. Enterprise EHR License Agreement No. CP-ENT-2022-0487, dated as of April 3, 2022, as amended, between Clearpath Health Systems, Inc. and Lakewood Regional Health Partners, LLC, together with the Assignment and Assumption Agreement dated as of August 15, 2025, by and among Lakewood Regional Health Partners, LLC, Crestline Packaging Solutions LLC, and Clearpath Health Systems, Inc. (as consented to by Clearpath Health Systems, Inc.).

7. Marlowe Asset Management Medical Equipment Finance, LLC Master Lease Agreement dated as of September 1, 2022, between Marlowe Asset Management Medical Equipment Finance, LLC and Lakewood Regional Health Partners, LLC, together with Lease Schedules VML-2023-1140, VML-2023-1141, and VML-2024-0219 (aggregate outstanding balance as of the date hereof of approximately $2,870,000), and the related Assignment and Assumption of Lease Schedules dated as of August 15, 2025.

8. Consulting Agreement, dated as of August 15, 2025, between Crestline Packaging Solutions LLC and Dr. Raymond Alcott.

9. Consulting Agreement, dated as of August 15, 2025, between Crestline Packaging Solutions LLC and Dr. Nadia Petrosian.

10. Limited Liability Company Agreement of Crestline Packaging Solutions LLC, dated as of July 14, 2020, as amended by First Amendment dated as of October 5, 2021, and Second Amendment dated as of August 14, 2025.

11. Such other material contracts and agreements identified on the disclosure schedules to the Asset Purchase Agreement and specifically designated by the Administrative Agent for review, as listed on Annex A to this Schedule I (which Annex A is on file with Calderwood & Harkness LLP and has been made available to the Administrative Agent).

Schedule I to Opinion Letter of Calderwood & Harkness LLP dated August 15, 2025 C&H Matter No. 1006-00008

CALDERWOOD & HARKNESS LLP Attorneys at Law
425 Lexington Avenue, 31st Floor New York, New York 10017
Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com
August 15, 2025
Ironclad National Bank, as Administrative Agent 301 South Tryon Street Charlotte, North Carolina 28202
Attention: Kenneth Boateng, Senior Vice President, Healthcare & Specialty Lending
Re: Amendment No. 3 to Credit Agreement dated September 17, 2021 (as amended) among Crestline Packaging Solutions LLC, CPS Holdings, Inc., the Lenders party thereto, and Ironclad National Bank, as Administrative Agent — Incremental Term Loan in the aggregate principal amount of $84,000,000
Ladies and Gentlemen:
I. Introduction
We have acted as counsel to Crestline Packaging Solutions LLC, a Delaware limited liability company ("Crestline" or the "Borrower"), and CPS Holdings, Inc., a Delaware corporation ("Holdings" and, together with the Borrower, the "Credit Parties"), in connection with (a) Amendment No. 3 ("Amendment No. 3") to the Credit Agreement dated as of September 17, 2021 (as amended by Amendment No. 1 dated March 22, 2023, Amendment No. 2 dated November 8, 2024, and as further amended, restated, supplemented, or otherwise modified from time to time, the "Credit Agreement"), among the Borrower, Holdings, the Lenders party thereto from time to time (the "Lenders"), and Ironclad National Bank, as administrative agent for the Lenders (in such capacity, the "Administrative Agent"), and (b) the incurrence of an incremental term loan in the aggregate principal amount of Eighty-Four Million Dollars ($84,000,000) (the "Incremental Term Loan") thereunder. Amendment No. 3 and the Credit Agreement are hereinafter referred to together with the other documents, instruments, and agreements executed and delivered in connection therewith (including the Amended and Restated Security Agreement, the Amended and Restated Guaranty Agreement, and the other Collateral Documents, each as defined in the Credit Agreement) as the "Financing Documents."
This opinion letter is delivered to you pursuant to Section 5.01(h) of Amendment No. 3 to the Credit Agreement as a condition precedent to the effectiveness thereof and the funding of the Incremental Term Loan on the date hereof (the "Closing Date"). Capitalized terms used but not otherwise defined herein shall have the meanings assigned to them in the Credit Agreement, as amended by Amendment No. 3.
II. Documents Examined
In rendering the opinions expressed herein, we have examined originals or copies, certified or otherwise identified to our satisfaction, of the following documents:
1. Amendment No. 3 to the Credit Agreement, dated as of the date hereof, among the Borrower, Holdings, the Lenders party thereto, and the Administrative Agent (the "Amendment");
2. The Credit Agreement dated as of September 17, 2021, among the Borrower, Holdings, the Lenders party thereto from time to time, and the Administrative Agent, as amended by Amendment No. 1 dated as of March 22, 2023, and Amendment No. 2 dated as of November 8, 2024;
3. The Incremental Term Loan Assumption Agreement executed by the Incremental Term Loan Lenders, dated as of the date hereof, together with the related Lender Joinder Agreements;
4. The Amended and Restated Security Agreement, dated as of the date hereof, among the Credit Parties and the Administrative Agent, for the benefit of the Secured Parties;
5. The Amended and Restated Guaranty Agreement, dated as of the date hereof, executed by Holdings in favor of the Administrative Agent, for the benefit of the Secured Parties;
6. The related Collateral Documents, including the Pledge Agreements, IP Security Agreements, and Deposit Account Control Agreements executed and delivered in connection with the Financing Documents;
7. The Asset Purchase Agreement, dated as of June 16, 2025 (the "APA"), by and among the Borrower, Lakewood Regional Health Partners, LLC ("Lakewood"), Dr. Raymond Alcott, and Dr. Nadia Petrosian, together with all schedules, exhibits, disclosure schedules, and ancillary documents thereto;
8. The Certificate of Formation of Crestline Packaging Solutions LLC, as filed with the Secretary of State of the State of Delaware on July 14, 2020, together with all amendments thereto, as certified by the Secretary of Crestline;
9. The Limited Liability Company Agreement of Crestline Packaging Solutions LLC, dated as of July 14, 2020, as amended to date (the "LLC Agreement"), as certified by the Secretary of Crestline;
10. The Certificate of Incorporation of CPS Holdings, Inc., as filed with the Secretary of State of the State of Delaware on June 29, 2020, together with all amendments thereto, as certified by the Secretary of CPS Holdings;
11. The Bylaws of CPS Holdings, Inc., as amended to date, as certified by the Secretary of CPS Holdings;
12. A Certificate of Good Standing for Crestline Packaging Solutions LLC issued by the Secretary of State of the State of Delaware, dated August 12, 2025;
13. A Certificate of Good Standing for CPS Holdings, Inc. issued by the Secretary of State of the State of Delaware, dated August 12, 2025;
14. Written consent of Pinnacle River GP IV, LLC, as the sole managing member of Crestline, dated as of August 14, 2025, approving and authorizing the execution, delivery, and performance by Crestline of the APA, Amendment No. 3, and the other Transaction Documents and Financing Documents to which Crestline is a party, and the consummation of the transactions contemplated thereby, including the incurrence of the Incremental Term Loan;
15. Resolutions of the Board of Directors of CPS Holdings, Inc., adopted by unanimous written consent dated as of August 14, 2025, authorizing the execution, delivery, and performance by CPS Holdings of each of the Financing Documents to which it is a party, including the Amended and Restated Guaranty Agreement, and the consummation of the transactions contemplated thereby;
16. An Officer's Certificate of Crestline Packaging Solutions LLC, dated as of the date hereof, executed by an authorized officer of Crestline, certifying as to, among other things, the incumbency and specimen signatures of the officers executing the Financing Documents and the APA on behalf of Crestline, the accuracy of the organizational documents of Crestline, and the satisfaction of certain conditions precedent set forth in Amendment No. 3;
17. An Officer's Certificate of CPS Holdings, Inc., dated as of the date hereof, executed by an authorized officer of CPS Holdings, certifying as to, among other things, the incumbency and specimen signatures of the officers executing the Financing Documents on behalf of CPS Holdings, the accuracy of the organizational documents of CPS Holdings, and the satisfaction of certain conditions precedent set forth in Amendment No. 3; and
18. Such other certificates, documents, instruments, corporate and limited liability company records, agreements, and other materials as we have deemed necessary or appropriate for the purposes of the opinions expressed herein.
In addition, we have reviewed such questions of law as we have considered necessary or appropriate for the purposes of the opinions expressed herein. We have also made such inquiries of officers and representatives of the Credit Parties as we have deemed relevant, and we have obtained and relied upon such certificates and assurances from officers and representatives of the Credit Parties and from public officials as we have deemed necessary or appropriate as a basis for the opinions set forth below.
III. Assumptions
In rendering the opinions set forth below, we have assumed, without independent investigation or verification, the following:
(a) The genuineness of all signatures on all documents examined by us, other than the signatures of officers and authorized representatives of the Credit Parties.
(b) The authenticity of all documents submitted to us as originals, the conformity to the originals of all documents submitted to us as copies (whether certified, photostatic, electronic, or otherwise), and the authenticity of the originals of such copies.
(c) The legal capacity of all natural persons who have executed any of the documents reviewed by us in connection with the rendering of this opinion.
(d) That each party to the Financing Documents (other than the Credit Parties) has been duly organized or formed, is validly existing and in good standing under the laws of its jurisdiction of organization or formation, and has all requisite power and authority to execute, deliver, and perform its obligations under each Financing Document to which it is a party.
(e) That Amendment No. 3, the Credit Agreement, and each of the other Financing Documents constitute the legal, valid, and binding obligations of each party thereto (other than the Credit Parties), enforceable against each such party in accordance with their respective terms.
(f) The accuracy and completeness of all factual matters set forth in all certificates, representations, and statements of fact furnished to us by officers and representatives of the Credit Parties, including the Officer's Certificates delivered on the date hereof, and that all such certificates, representations, and statements remain true and correct as of the date hereof. We have not undertaken any independent investigation to verify the accuracy or completeness of any such factual matters.
(g) That there has been no mutual mistake of fact or misunderstanding, fraud, duress, undue influence, or other irregularity with respect to the negotiation, execution, or delivery of any of the Financing Documents or the APA.
(h) That the conduct of the parties to the Financing Documents has complied and will comply with any requirement of good faith, fair dealing, and conscionability applicable thereto.
(i) That the Administrative Agent and the Lenders have acted in good faith, without notice of any defense against the enforcement of any rights created by, or any defect in or objection to the validity or enforceability of, any of the Financing Documents, and without notice of any facts that would give rise to a personal defense of any party to any of the Financing Documents.
(j) That the Credit Agreement, as amended by Amendment No. 3, accurately reflects the complete agreement of the parties thereto with respect to the matters set forth therein, and that there are no oral or written agreements, understandings, or courses of dealing between the parties that would modify, amend, or supplement the terms of the Credit Agreement as so amended.
IV. Opinions
Based upon the foregoing, and subject to the assumptions, qualifications, limitations, and exceptions set forth herein, we are of the opinion that:
Opinion 1 — Due Organization and Good Standing of Crestline. Crestline Packaging Solutions LLC is a limited liability company duly formed, validly existing, and in good standing under the laws of the State of Delaware. In rendering this opinion, we have relied exclusively upon the Certificate of Good Standing issued by the Secretary of State of the State of Delaware dated August 12, 2025, the Certificate of Formation of Crestline (as certified to us), and the Officer's Certificate of Crestline delivered on the date hereof.
Opinion 2 — Due Organization and Good Standing of CPS Holdings. CPS Holdings, Inc. is a corporation duly incorporated, validly existing, and in good standing under the laws of the State of Delaware. In rendering this opinion, we have relied exclusively upon the Certificate of Good Standing issued by the Secretary of State of the State of Delaware dated August 12, 2025, the Certificate of Incorporation of CPS Holdings (as certified to us), and the Officer's Certificate of CPS Holdings delivered on the date hereof.
Opinion 3 — Power and Authority of Crestline. Crestline has the limited liability company power and authority to (a) own, lease, and operate its properties and assets and to carry on its business as presently conducted, (b) execute, deliver, and perform its obligations under each of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and (c) consummate the transactions contemplated thereby, including the acquisition of the Purchased Assets (as defined in the APA) from Lakewood Regional Health Partners, LLC, Dr. Raymond Alcott, and Dr. Nadia Petrosian and the incurrence of the Incremental Term Loan in the aggregate principal amount of Eighty-Four Million Dollars ($84,000,000).
Opinion 4 — Power and Authority of CPS Holdings. CPS Holdings, Inc. has the corporate power and authority to execute, deliver, and perform its obligations under each of the Financing Documents to which it is a party, including, without limitation, the Amended and Restated Guaranty Agreement, and to consummate the transactions contemplated thereby.
Opinion 5 — Due Authorization — Crestline. The execution, delivery, and performance by Crestline of the APA, Amendment No. 3, and each other Financing Document to which it is a party, and the consummation of the transactions contemplated thereby (including the acquisition of the Purchased Assets and the incurrence of the Incremental Term Loan), have been duly authorized by all necessary limited liability company action on the part of Crestline. Such authorization includes the written consent of Pinnacle River GP IV, LLC, as the sole managing member of Crestline, dated August 14, 2025, which consent was duly adopted in accordance with the LLC Agreement and the Delaware Limited Liability Company Act, 6 Del. C. § 18-101 et seq. No further approval, consent, or authorization of any member, manager, or other person or entity is required for the valid execution, delivery, and performance by Crestline of such documents or the consummation of such transactions.
Opinion 6 — Due Authorization — CPS Holdings. The execution, delivery, and performance by CPS Holdings of each Financing Document to which it is a party, and the consummation of the transactions contemplated thereby, have been duly authorized by all necessary corporate action on the part of CPS Holdings, including the unanimous written consent of the Board of Directors of CPS Holdings dated August 14, 2025. No stockholder approval is required under the Delaware General Corporation Law, the Certificate of Incorporation, or the Bylaws of CPS Holdings for the execution, delivery, and performance of any such Financing Document or the consummation of any such transactions.
Opinion 7 — Execution and Delivery. Each of the APA, Amendment No. 3, and the other Financing Documents to which any Credit Party is a party has been duly executed and delivered by such Credit Party. The persons who executed such documents on behalf of each Credit Party were, at the time of such execution, duly authorized to do so.
Opinion 8 — Enforceability. Each of the APA, Amendment No. 3, and the other Financing Documents to which any Credit Party is a party constitutes the legal, valid, and binding obligation of such Credit Party, enforceable against such Credit Party in accordance with its respective terms, subject, however, to the Enforceability Qualifications set forth in Section VI(A) below.
Opinion 9 — No Conflicts — Organizational Documents. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby (including the acquisition of the Purchased Assets and the incurrence of the Incremental Term Loan), do not and will not (a) violate, conflict with, or result in a breach of any provision of the Certificate of Formation or the Limited Liability Company Agreement of Crestline Packaging Solutions LLC, or (b) violate, conflict with, or result in a breach of any provision of the Certificate of Incorporation or Bylaws of CPS Holdings, Inc.
Opinion 10 — No Conflicts — Laws. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby (including the acquisition of the Purchased Assets and the incurrence of the Incremental Term Loan), do not and will not violate any law, statute, rule, or regulation of the State of New York, the State of Delaware, or the federal laws of the United States of America that, in our experience, are normally applicable to transactions of this type and that we, in the exercise of customary professional diligence, would reasonably recognize as being applicable to the Credit Parties or the transactions contemplated by the Financing Documents (collectively, the "Opined-Upon Laws"). We express no opinion with respect to any laws, statutes, rules, or regulations other than the Opined-Upon Laws, and we note in particular that this opinion does not address the healthcare regulatory laws, licensure requirements, certificate-of-need laws, or similar regulatory frameworks of any jurisdiction, including the State of New York and the Commonwealth of Pennsylvania, as discussed in Section VI(C) below.
Opinion 11 — No Conflicts — Orders and Judgments. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby, do not and will not, to our knowledge (as defined in Section V below, and based solely on inquiry of Derek Okonkwo and Tiffany Rosenthal, each of whom has had primary responsibility for representing the Credit Parties in connection with this matter), violate any order, judgment, injunction, writ, or decree of any court or governmental authority binding upon any Credit Party or any of its properties or assets.
Opinion 12 — No Conflicts — Material Agreements. The execution, delivery, and performance by each Credit Party of the APA, Amendment No. 3, and the other Financing Documents to which it is a party, and the consummation of the transactions contemplated thereby, do not and will not result in a breach of, constitute a default (or an event that, with the giving of notice or lapse of time, or both, would constitute a default) under, require any consent not already obtained under, or give rise to any right of termination, cancellation, acceleration, or loss of any material benefit under, any of the material agreements, contracts, and instruments listed on Schedule I hereto (collectively, the "Reviewed Agreements"), except where such breach, default, or right would not reasonably be expected to have a Material Adverse Effect (as defined in the Credit Agreement). Our opinion in this paragraph is limited solely to the Reviewed Agreements listed on Schedule I and does not extend to any other agreement, contract, instrument, or arrangement to which any Credit Party may be a party or by which any Credit Party or its properties or assets may be bound.
Opinion 13 — Governmental Approvals. No consent, approval, authorization, order, license, permit, registration, qualification, or filing with any federal, state, or local governmental authority under the Opined-Upon Laws is required for the execution, delivery, and performance by any Credit Party of Amendment No. 3 or the other Financing Documents to which it is a party, or for the incurrence of the Incremental Term Loan, except for (a) those consents, approvals, authorizations, orders, registrations, qualifications, and filings that have been obtained or made on or prior to the date hereof and are in full force and effect as of the date hereof, (b) the filing of UCC-1 financing statements (and continuation statements in connection therewith) in the office of the Secretary of State of the State of Delaware (with respect to each of Crestline and CPS Holdings, as debtors organized in Delaware) and in such other filing offices as may be necessary or appropriate to perfect the security interests created by the Collateral Documents, and (c) the approvals of the New York State Department of Health and the Pennsylvania Department of Health with respect to the change-of-ownership and operation of the clinical facilities being acquired pursuant to the APA, which approvals are conditions to Closing under the APA and are not required for the effectiveness of Amendment No. 3 or the incurrence of the Incremental Term Loan on the date hereof.
Opinion 14 — Security Interest (UCC). Amendment No. 3 and the Amended and Restated Security Agreement are effective to create in favor of the Administrative Agent, for the benefit of the Secured Parties, a valid security interest in all right, title, and interest of each of the Credit Parties in the Collateral described in the Amended and Restated Security Agreement, to the extent that Article 9 of the Uniform Commercial Code as in effect in the State of New York (the "NY UCC") is applicable to the creation of such security interest. Upon the filing of duly completed UCC-1 financing statements, in proper form for filing under Article 9 of the NY UCC, in the office of the Secretary of State of the State of Delaware (with respect to each of Crestline Packaging Solutions LLC and CPS Holdings, Inc., each as a debtor organized in the State of Delaware), such security interest will be perfected to the extent that a security interest in such Collateral may be perfected by the filing of a financing statement under the NY UCC. We express no opinion as to the perfection of any security interest in any Collateral consisting of (i) deposit accounts (which require control for perfection under Section 9-314 of the NY UCC), (ii) letter-of-credit rights (which require control for perfection under Section 9-314 of the NY UCC), (iii) electronic chattel paper (which requires control for perfection under Section 9-105 of the NY UCC), (iv) assets subject to a federal statute, regulation, or treaty that preempts Article 9 of the NY UCC, (v) real property or fixtures, or (vi) motor vehicles or other property subject to certificate-of-title statutes. We express no opinion as to the priority of any security interest.
Opinion 15 — Investment Company Act. Neither Crestline Packaging Solutions LLC nor CPS Holdings, Inc. is, or upon the consummation of the transactions contemplated by Amendment No. 3 and the other Financing Documents will be required to be, registered as an "investment company" within the meaning of the Investment Company Act of 1940, as amended.
V. Certain Additional Matters — Knowledge Qualifications
As used in this opinion letter, the phrases "to our knowledge," "known to us," and similar phrases with respect to matters of fact mean the actual knowledge, as of the date hereof and without independent investigation, of James Prentice, Sandra Tung, Derek Okonkwo, and Tiffany Rosenthal, each of whom is an attorney at this firm and has had substantive involvement in the representation of the Credit Parties in connection with the transactions described herein. We have not conducted any independent investigation or inquiry for the purpose of this opinion letter beyond the examination of the documents identified in Section II above and the inquiries described therein. No inference as to our knowledge of any fact or matter should be drawn from the absence of a knowledge qualification in any other opinion expressed herein.
VI. Qualifications and Limitations
The opinions set forth herein are subject to the following qualifications and limitations:
A. Enforceability Qualifications
The opinions expressed herein regarding the enforceability of the Financing Documents, the APA, and any other document or instrument are subject to and limited by:
(i) The effect of applicable bankruptcy, insolvency, reorganization, receivership, moratorium, fraudulent conveyance, fraudulent transfer, preferential transfer, and other similar laws now or hereafter in effect relating to or affecting creditors' rights and remedies generally, including, without limitation, the United States Bankruptcy Code (Title 11 of the United States Code) and the laws of the State of New York relating to fraudulent conveyances and transfers (Article 10 of the New York Debtor and Creditor Law);
(ii) The effect of general principles of equity, whether applied in a proceeding in equity or at law (including, without limitation, concepts of materiality, reasonableness, good faith, and fair dealing), and the discretionary nature of equitable remedies (including, without limitation, the remedies of specific performance and injunctive relief), regardless of whether enforceability is considered in a proceeding in equity or at law;
(iii) The qualification that certain provisions of the Financing Documents may be unenforceable in whole or in part under applicable law, but such unenforceability does not, in our opinion, render the Financing Documents invalid as a whole, and there exist in the Financing Documents or are otherwise available at law or in equity adequate remedies for the practical realization of the principal benefits intended to be provided thereby;
(iv) Limitations that may be imposed by law on the enforceability of provisions in the Financing Documents relating to indemnification, contribution, and exculpation to the extent that such provisions may contravene applicable law or public policy, including, without limitation, federal and state securities laws; and
(v) The effect of judicial decisions that may permit the introduction of extrinsic evidence to modify the terms or the interpretation of the Financing Documents.
The qualifications set forth in clauses (i) through (v) above are collectively referred to herein as the "Enforceability Qualifications."
B. Law Covered
The opinions expressed herein are limited in all respects to the laws of the State of New York (excluding the choice-of-law rules thereof, except as set forth in Section VI(D) below), the General Corporation Law of the State of Delaware (Title 8, Chapter 1 of the Delaware Code), the Limited Liability Company Act of the State of Delaware (Title 6, Chapter 18 of the Delaware Code), and the federal laws of the United States of America, in each case as currently in effect on the date hereof. We express no opinion as to the laws of any other jurisdiction, and we assume no obligation to advise you of any changes in law after the date hereof. Without limiting the generality of the foregoing, we express no opinion as to the healthcare regulatory laws, licensure requirements, certificate-of-need requirements, change-of-ownership regulations, Medicare or Medicaid participation requirements, or any other healthcare-related regulatory requirements of the State of New York, the Commonwealth of Pennsylvania, or any other jurisdiction. We understand that such matters have been separately addressed by Marchand Healthcare Regulatory Advisors, LLC in a separate opinion letter delivered to the Administrative Agent on or about the date hereof. In addition, we express no opinion with respect to any state or local tax laws or regulations.
C. No Opinion on Certain Matters
Without limiting the generality of Section VI(B) above, we express no opinion as to:
(i) The compliance by any Credit Party with, or the effect of, any financial covenants, financial tests, financial ratios, or other financial requirements set forth in the Credit Agreement, Amendment No. 3, or any other Financing Document, including, without limitation, the Consolidated Leverage Ratio, the Consolidated Interest Coverage Ratio, the Minimum Liquidity Covenant, or any pro forma financial tests required in connection with the incurrence of the Incremental Term Loan;
(ii) The effect of any future changes in applicable law, regulation, or administrative practice occurring after the date hereof;
(iii) The title of any Credit Party to any real or personal property, or the priority of any lien, security interest, mortgage, pledge, or other encumbrance, except as expressly set forth in Opinion 14 above;
(iv) Federal or state antitrust or competition laws, including, without limitation, the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended;
(v) Federal, state, or local environmental laws, regulations, or standards, including, without limitation, the Comprehensive Environmental Response, Compensation, and Liability Act, the Resource Conservation and Recovery Act, and any state equivalents thereof;
(vi) The Employee Retirement Income Security Act of 1974, as amended ("ERISA"), or any other federal, state, or local law relating to employee benefit plans, pension plans, or welfare benefit plans, or any matters arising thereunder;
(vii) Federal, state, or local tax laws or regulations, including, without limitation, the Internal Revenue Code of 1986, as amended, and any state or local tax codes;
(viii) Laws, rules, and regulations of the Federal Drug Enforcement Administration, the federal Controlled Substances Act, or any state controlled substance regulations;
(ix) Federal or state healthcare fraud and abuse laws, the Physician Self-Referral Law (commonly known as the "Stark Law"), 42 U.S.C. § 1395nn, the Federal Anti-Kickback Statute, 42 U.S.C. § 1320a-7b(b), the False Claims Act, 31 U.S.C. §§ 3729–3733, the Health Insurance Portability and Accountability Act of 1996 ("HIPAA"), the Health Information Technology for Economic and Clinical Health Act (the "HITECH Act"), or any state equivalents of any of the foregoing; and
(x) Federal, state, or local laws relating to intellectual property, including, without limitation, patent, trademark, copyright, and trade secret laws.
D. Additional Customary Qualifications
In addition to the Enforceability Qualifications and the other qualifications and limitations set forth above, the opinions expressed herein are subject to the following additional customary qualifications:
(i) Provisions of the Financing Documents that purport to establish evidentiary standards, or that purport to make determinations conclusive, may be limited or rendered unenforceable by applicable law.
(ii) Provisions of the Financing Documents that purport to constitute a waiver of rights or defenses, including, without limitation, waivers of the right to a jury trial, waivers of objections to venue, waivers of rights to assert counterclaims or setoffs, waivers of statutes of limitations, and similar waivers, may be limited or rendered unenforceable by applicable law.
(iii) While we express no opinion as to the enforceability of the choice-of-law provisions of the Financing Documents in all circumstances under New York conflicts-of-law principles, we note that, under Section 5-1401 of the New York General Obligations Law, a New York court should give effect to the selection of New York law set forth in the Financing Documents, provided the transaction bears a reasonable relation to the State of New York or involves an aggregate consideration of not less than $250,000, and we believe that such conditions are satisfied in the case of the Financing Documents.
(iv) We express no opinion that any guarantee provided by Holdings under the Amended and Restated Guaranty Agreement constitutes a "guaranty of payment" rather than a "guaranty of collection," except to the extent expressly provided in the terms of the Amended and Restated Guaranty Agreement itself. The characterization of any guarantee as absolute and unconditional may be subject to judicial interpretation.
(v) We express no opinion as to the enforceability of any provision of the Financing Documents that purports to grant any power of attorney to the extent that such grant may be revocable under applicable law.
(vi) We express no opinion as to the enforceability of any provision of the Financing Documents to the extent it purports to waive or limit the effect of applicable law governing the time within which suit must be commenced under any statute of limitations.
VII. Reliance and Distribution
This opinion letter is rendered solely for the benefit of the Administrative Agent and the Lenders under the Credit Agreement as of the date hereof, in their respective capacities as such, and solely in connection with the transactions contemplated by Amendment No. 3 and the incurrence of the Incremental Term Loan. This opinion letter may not be relied upon by any other person or entity, or for any other purpose, without our prior written consent. This opinion letter may not be quoted or referred to in any public document, public filing, or registration statement, or furnished to any other person or entity, without our prior written consent.
Notwithstanding the foregoing, this opinion letter may be disclosed to (a) prospective assignees and participants in the Incremental Term Loan and the other Loans and Commitments under the Credit Agreement, in accordance with the terms and conditions of the Credit Agreement (including Section 10.06 thereof), provided that such prospective assignees and participants are informed that (i) this opinion letter speaks only as of its date, (ii) such persons may not rely on this opinion letter without our prior written consent, and (iii) we undertake no obligation to update or supplement this opinion letter for the benefit of any such person; and (b) bank examiners, auditors, and regulatory authorities having jurisdiction over the Administrative Agent or any Lender, provided such disclosure is required by applicable law or regulation and such persons are informed that they may not rely on this opinion letter.
This opinion letter is rendered as of the date hereof, and we express no opinion as to facts, events, transactions, changes in law, or changes in circumstances occurring after the date hereof. We undertake no obligation, and hereby disclaim any obligation, to update or supplement this opinion letter, or to advise you or any other person of any changes in law or fact that may come to our attention after the date hereof, whether or not such changes would affect the opinions expressed herein.
VIII. Governing Law of Opinion Letter
This opinion letter shall be governed by, and construed in accordance with, the laws of the State of New York (without regard to the conflicts-of-law principles thereof, other than Section 5-1401 of the New York General Obligations Law).
[Remainder of page intentionally left blank; signature page follows.]
Very truly yours,
CALDERWOOD & HARKNESS LLP
By: ________
James Prentice, Partner
C&H Matter No. 1006-00008
JPrentice/STung/DOkonkwo/TRosenthal Enclosure: Schedule I
SCHEDULE I
Reviewed Agreements
(Referenced in Opinion 12)
The following is the list of material agreements, contracts, and instruments reviewed by Calderwood & Harkness LLP in connection with the no-conflicts opinion set forth in Opinion 12 of this opinion letter (collectively, the "Reviewed Agreements"):
1. Credit Agreement dated as of September 17, 2021, among Crestline Packaging Solutions LLC, CPS Holdings, Inc., the Lenders party thereto from time to time, and Ironclad National Bank, as Administrative Agent, as amended by Amendment No. 1 dated as of March 22, 2023, Amendment No. 2 dated as of November 8, 2024, and Amendment No. 3 dated as of the date hereof.
2. Amended and Restated Security Agreement, dated as of August 15, 2025, among Crestline Packaging Solutions LLC, CPS Holdings, Inc., and Ironclad National Bank, as Administrative Agent, for the benefit of the Secured Parties.
3. Amended and Restated Guaranty Agreement, dated as of August 15, 2025, executed by CPS Holdings, Inc. in favor of Ironclad National Bank, as Administrative Agent, for the benefit of the Secured Parties.
4. Asset Purchase Agreement, dated as of June 16, 2025, by and among Crestline Packaging Solutions LLC, Lakewood Regional Health Partners, LLC, Dr. Raymond Alcott, and Dr. Nadia Petrosian, together with all exhibits, schedules, and disclosure schedules thereto.
5. Escrow Agreement, dated as of August 15, 2025, among Crestline Packaging Solutions LLC, Lakewood Regional Health Partners, LLC, and Apex Title & Escrow Services, LLC, as escrow agent, with respect to (a) the Indemnification Escrow in the amount of $35,000,000 and (b) the Purchase Price Adjustment Escrow in the amount of $3,500,000.
6. Clearpath Health Systems, Inc. Enterprise EHR License Agreement No. CP-ENT-2022-0487, dated as of April 3, 2022, as amended, between Clearpath Health Systems, Inc. and Lakewood Regional Health Partners, LLC, together with the Assignment and Assumption Agreement dated as of August 15, 2025, by and among Lakewood Regional Health Partners, LLC, Crestline Packaging Solutions LLC, and Clearpath Health Systems, Inc. (as consented to by Clearpath Health Systems, Inc.).
7. Marlowe Asset Management Medical Equipment Finance, LLC Master Lease Agreement dated as of September 1, 2022, between Marlowe Asset Management Medical Equipment Finance, LLC and Lakewood Regional Health Partners, LLC, together with Lease Schedules VML-2023-1140, VML-2023-1141, and VML-2024-0219 (aggregate outstanding balance as of the date hereof of approximately $2,870,000), and the related Assignment and Assumption of Lease Schedules dated as of August 15, 2025.
8. Consulting Agreement, dated as of August 15, 2025, between Crestline Packaging Solutions LLC and Dr. Raymond Alcott.
9. Consulting Agreement, dated as of August 15, 2025, between Crestline Packaging Solutions LLC and Dr. Nadia Petrosian.
10. Limited Liability Company Agreement of Crestline Packaging Solutions LLC, dated as of July 14, 2020, as amended by First Amendment dated as of October 5, 2021, and Second Amendment dated as of August 14, 2025.
11. Such other material contracts and agreements identified on the disclosure schedules to the Asset Purchase Agreement and specifically designated by the Administrative Agent for review, as listed on Annex A to this Schedule I (which Annex A is on file with Calderwood & Harkness LLP and has been made available to the Administrative Agent).
Schedule I to Opinion Letter of Calderwood & Harkness LLP dated August 15, 2025 C&H Matter No. 1006-00008

CALDERWOOD & HARKNESS LLP Attorneys at Law

CALDERWOOD & HARKNESS LLP

SCHEDULE I

Record

Parties

Dates

Amounts