Massachusetts Mutual Life Insurance Company Announces Pricing of Private Exchange Offers for Any and All of Its Outstanding 5⅝% Surplus Notes due 2033, 8⅞% Surplus Notes due 2039, 5⅜% Surplus Notes due 2041 and 4½% Surplus Notes due 2065

SPRINGFIELD, Mass., Oct. 8, 2019 /PRNewswire/ -- Massachusetts Mutual Life Insurance Company ("MassMutual") today announced the pricing terms, determined today as of 2:00 p.m., New York City time (the "Price Determination Time"), of its previously announced four separate exchange offers (each an "Exchange Offer" and, collectively, the "Exchange Offers") for any and all of its outstanding 5⅝% Surplus Notes due 2033 (the "2033 Surplus Notes"), 8⅞% Surplus Notes due 2039 (the "2039 Surplus Notes"), 5⅜% Surplus Notes due 2041 (the "2041 Surplus Notes") and 4½% Surplus Notes due 2065 (the "2065 Surplus Notes" and, together with the 2033 Surplus Notes, the 2039 Surplus Notes and the 2041 Surplus Notes, the "Tendered Surplus Notes") held by Eligible Holders (as defined below). The Tendered Surplus Notes are being exchanged for consideration consisting of MassMutual's Surplus Notes due 2070 (the "New Surplus Notes") and, if applicable, cash equal to the applicable Exchange Consideration (as defined below). The New Surplus Notes will bear interest at a fixed rate equal to 3.729% per year, which interest rate was calculated in accordance with the Offering Memorandum (as defined below).

The exchange consideration (the "Exchange Consideration") to be received by Eligible Holders for each $1,000 principal amount of the applicable series of Tendered Surplus Notes validly tendered and not validly withdrawn prior to 5:00 p.m., New York City time, on October 8, 2019, unless extended or terminated by MassMutual (such date and time, as the same may be extended or terminated, the "Expiration Time") is set forth in the table below.

The Exchange Offers are being made solely to Eligible Holders upon the terms and subject to the conditions set forth in the confidential offering memorandum (as it may be amended or supplemented from time to time, the "Offering Memorandum"), and the related notice of guaranteed delivery (as it may be amended or supplemented from time to time, the "Notice of Guaranteed Delivery", and collectively with the Offering Memorandum, the "Exchange Offer Materials"), each dated October 2, 2019.

The Exchange Offers are being made, and the New Surplus Notes are being offered and issued, only (i) in the United States, to holders of Tendered Surplus Notes who are "qualified institutional buyers," as defined in Rule 144A under the Securities Act of 1933, as amended (the "Securities Act"), (ii) to a limited number of institutional "accredited investors" within the meaning of Rule 501(a)(1), (2), (3) or (7) under the Securities Act, and (iii) outside the United States, to holders of Tendered Surplus Notes who are not "U.S. persons," as defined in Rule 902 under the Securities Act in reliance on Regulation S under the Securities Act. MassMutual refers to the holders of Tendered Surplus Notes who have certified that they are eligible to participate in any of the Exchange Offers pursuant to at least one of the foregoing conditions as "Eligible Holders."

Each Exchange Offer will expire at the Expiration Time. Each Exchange Offer may be terminated or withdrawn at any time, in MassMutual's sole and absolute discretion, subject to compliance with applicable law. If any of the Exchange Offers is terminated at any time, the Tendered Surplus Notes tendered pursuant to the applicable Exchange Offer will be promptly returned to the tendering holders. MassMutual reserves the right, subject to applicable law, to (i) waive any and all conditions to any of the Exchange Offers, (ii) extend or terminate any of the Exchange Offers or (iii) otherwise amend any of the Exchange Offers in any respect. The Exchange Offers are subject to the conditions described in the Offering Memorandum, including the valid issuance of a minimum of $300,000,000 aggregate principal amount of New Surplus Notes, unless waived by MassMutual.

The settlement date will be promptly following the Expiration Time and is expected to be October 11, 2019 (the "Settlement Date"), which is three business days after the Expiration Time. Tendered Surplus Notes validly tendered pursuant to the guaranteed delivery procedures set forth in the Exchange Offer Materials and accepted for exchange by MassMutual in any Exchange Offer are expected to settle on the Settlement Date.

The complete terms and conditions of each Exchange Offer are described in the Exchange Offer Materials, copies of which may be obtained by Eligible Holders by contacting D.F. King & Co., Inc., the information and exchange agent for the Exchange Offers (the "Information and Exchange Agent"), at (866) 829-0542 (toll-free) or (212) 269-5550 (collect) or by visiting www.dfking.com/massmutual to complete the eligibility process.

In connection with any Exchange Offer, Holders who are not Eligible Holders may contact the Information and Exchange Agent, at (866) 829-0542 (toll-free) or (212) 269-5550 (collect) or by visiting www.dfking.com/massmutual, for further instructions on how to receive cash consideration for their applicable series of Tendered Surplus Notes in an amount intended to approximate the value of the Exchange Consideration related thereto.

This press release is for informational purposes only and is neither an offer to purchase nor a solicitation of an offer to sell any securities. The Exchange Offers are being made and the New Surplus Notes are being offered only to Eligible Holders. The New Surplus Notes have not been registered under the Securities Act or under any state or foreign securities laws, and may not be offered or sold in the United States absent registration or an applicable exemption from the registration requirements of the Securities Act, and, accordingly, are subject to significant restrictions on transfer and resale as more fully described in the Exchange Offer Materials. The Exchange Offers are subject to the terms and conditions set forth in the Exchange Offer Materials.

Forward-Looking Statements

This press release may contain "forward-looking statements." Forward-looking statements are those not based on historical information, but rather, relate to future operations, strategies, financial results or other developments, and contain terms such as "may," "expects," "should," "believes," "anticipates," "intends," "estimates," "projects," "goals," "objectives" or similar expressions. Forward-looking statements are based upon estimates and assumptions. These statements may change due to business uncertainties, economic uncertainties, competitive uncertainties, and other factors, many of which are beyond MassMutual's control. Additionally, MassMutual's business decisions are also subject to change. MassMutual does not publicly update or revise any forward-looking statements as a result of new information, future developments or otherwise except as may be required by law. Forward-looking statements are not guarantees of future performance and involve risks and uncertainties and actual results may differ materially from those in the forward-looking statements as a result of various factors.

About MassMutual

MassMutual is a leading mutual life insurance company that is run for the benefit of its members and participating policyowners. MassMutual offers a wide range of financial products and services, including life insurance, disability income insurance, long term care insurance, annuities, retirement plans and other employee benefits. For more information, visit www.MassMutual.com.

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