Contract analysis

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

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 Incr

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 s

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 Amendm

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 office

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 documen

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 relie

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 involveme

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, fr

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

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, P

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

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 Assumpt

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, 20