Supplemental Indenture No. 2, dated as of October 11, 2019, among Cigna Holding Company, as Issuer, Cigna Corporation, as parent guarantor, and HSBC Bank USA, National Association, as trustee

Exhibit 4.4

SUPPLEMENTAL INDENTURE NO. 2

THIS SUPPLEMENTAL INDENTURE NO. 2, dated as of October 11, 2019 (this “Supplemental Indenture No. 2”), among CIGNA HOLDING COMPANY, a corporation organized and existing under the laws of the State of Delaware (the “Company”), CIGNA CORPORATION, a corporation organized and existing under the laws of the State of Delaware, and the Company’s parent company (“Cigna”) and HSBC BANK USA, National Association (as successor to Marine Midland Bank, N.A.), as trustee (the “Trustee”).

RECITALS OF THE COMPANY:

WHEREAS, the Company and the Trustee are parties to an Indenture, dated as of January 1, 1994 (the “Base Indenture” and, as amended, supplemented and otherwise modified on or prior to the date hereof, including by this Supplemental Indenture No. 2, the “Indenture”), relating to the issuance from time to time by the Company of its Securities on terms specified at the time of issuance;

WHEREAS, pursuant to the Base Indenture, the Company has issued its 7.875% Debentures due 2027 and its 8.300% Step-Down Notes due 2033 (together, the “Securities”);

WHEREAS, Section 902 of the Base Indenture provides that the Indenture may be amended with the consent of the Holders of not less than 66^2/3% in aggregate principal amount of the Outstanding Securities of each series affected by such supplemental indenture (the “Requisite Consents”), subject to certain exceptions specified in Section 902 of the Base Indenture;

WHEREAS, Cigna has, on the Company’s behalf, solicited consents (the “Consent Solicitation”) from eligible holders of the Securities to effectuate certain proposed amendments to the Indenture as set forth herein (the “Proposed Amendments”), pursuant to the terms of Cigna’s Offering Memorandum and Consent Solicitation Statement, dated as of September 26, 2019;

WHEREAS, the Requisite Consents for the adoption of the Proposed Amendments have been obtained, and this Supplemental Indenture No. 2 complies with the requirements of Article Nine of the Base Indenture and is authorized and permitted by the Indenture, all as certified by an Officer’s Certificate by certain officers of the Company delivered to the Trustee simultaneously with the execution and delivery of this Supplemental Indenture No. 2;

WHEREAS, the Company desires and has requested the Trustee to join with it in entering into this Supplemental Indenture No. 2 for the purpose of amending the Indenture to adopt the Proposed Amendments as permitted by Section 902 of the Base Indenture; and

WHEREAS, the execution and delivery of this Supplemental Indenture No. 2 has been authorized by a Board Resolution.

NOW, THEREFORE, for and in consideration of the above premises, each party hereby agrees, for the benefit of the others and for the equal and ratable benefit of the Holders of the Securities, as follows:

SECTION 1. Capitalized Terms. For purposes of this Supplemental Indenture No. 2:

(a)                      Capitalized terms used herein without definition shall have the meanings assigned to them in the Base Indenture;

(b)                     All references to Articles and Sections, unless otherwise specified, refer to the corresponding Articles and Sections of the Base Indenture; and

(c)                      The terms “herein,” hereof,” “hereunder” and other words of similar import refer to this Supplemental Indenture No. 2.

SECTION 2. Proposed Amendments. The following provisions of the Base Indenture shall, from the date hereof, no longer be applicable to the Securities:

Any and all references to any provisions of the Indenture or any of the Global Securities for the Securities which are not applicable to the Securities, as applicable, by virtue of any provision of this Supplemental Indenture No. 2 and any and all obligations thereunder related solely to such deleted provision throughout the Indenture or any of the Global Securities for the Securities are of no further force or effect with respect to the Securities, as applicable. Any and all terms defined in the Indenture or any of the Global Securities for the Securities which are used in any provision of the Indenture or any of the Global Securities for the Securities which are not applicable to the

Securities, as applicable, by virtue of any provision of this Supplemental Indenture No. 2 and which are not otherwise used in any other provision of the Indenture or any of the Global Securities for the Securities not affected by this Supplemental Indenture No. 2 are hereby deleted in full.

SECTION 3. Integral Part; Effect of Supplement on Indenture. This Supplemental Indenture No. 2 constitutes an integral part of the Indenture. Except for the amendments and supplements made by this Supplemental Indenture No. 2, the Base Indenture shall remain in full force and effect as executed.

SECTION 4. Adoption, Ratification and Confirmation. The Indenture, as supplemented by this Supplemental Indenture No. 2, is in all respects hereby adopted, ratified and confirmed.

SECTION 5. Trustee Not Responsible for Recitals. The recitals in this Supplemental Indenture No. 2 are made by the Company, and the Trustee assumes no responsibility for the correctness of such recitals.  The Trustee makes no representations as to the validity or sufficiency of this Supplemental Indenture No. 2.

SECTION 6. Counterparts. This Supplemental Indenture No. 2 may be executed in multiple counterparts, each of which shall be regarded for all purposes as an original and all of which shall constitute but one and the same instrument.

SECTION 7. Governing Law. This Supplemental Indenture No. 2 and the Parent Guarantee hereunder shall be governed by and construed in accordance with the laws of the State of New York.

SECTION 8. Conflict with Trust Indenture Act. If any provision of this Supplemental Indenture No. 2 limits, qualifies or conflicts with any provision of the Trust Indenture Act that is required under the Trust Indenture Act to be part of and govern this Supplemental Indenture No. 2, the latter provision shall control. If any provision of this Supplemental Indenture No. 2 modifies or excludes any provision of the Trust Indenture Act which may be so modified or excluded, the latter provision shall be deemed to apply to the Supplemental Indenture No. 2 as so modified or to be excluded, as the case may be.

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IN WITNESS WHEREOF, the parties hereto have caused this Supplemental Indenture No. 2 to be duly executed as of the date first above written.

[Signature Page to Supplemental Indenture No. 2]