MassMutual Capital Vantage

MassMutual Capital Vantage A Flexible Premium Deferred Variable Annuity

TABLE OF CONTENTS 2 Sophisticated simplicity 3 Tax-deferred growth potential 4 How Capital Vantage works 10 Generating a retirement income stream 11 Tax-efficient annuity payments 12 Product highlights NOT A BANK OR CREDIT UNION DEPOSIT OR OBLIGATION NOT FDIC OR NCUA INSURED NOT INSURED BY ANY FEDERAL GOVERNMENT AGENCY NOT GUARANTEED BY ANY BANK OR CREDIT UNION MAY LOSE VALUE

MassMutual Capital Vantage MassMutual Capital Vantage (Capital Vantage) is a flexible premium deferred variable annuity issued by Massachusetts Mutual Life Insurance Company (MassMutual). Whether you are interested in choosing from a broad selection of underlying funds or are seeking a single-fund solution, Capital Vantage may be the right choice for you. A variable annuity is a long-term investment designed to help you accumulate assets for retirement. It also offers a broad array of investment choices as well as a death benefit and multiple methods to turn those assets into a stream of guaranteed income at some point in the future. There are fees and charges associated with owning a variable annuity. Variable annuities are subject to market risk, including the potential loss of principal. Also, withdrawals of earnings will be subject to ordinary income tax and may be subject to an additional 10 percent federal income tax if taken prior to age 59½. 1

Sophisticated simplicity Your investment needs and preferences will likely change during your lifetime. During certain periods, you may be more aggressive in your investment approach depending on your time horizon, risk tolerance, and investment objectives. Massachusetts Mutual Life Insurance Company (MassMutual) recognizes that all investors are not alike in selecting investments that meet their needs. Some investors may prefer a simplified approach that uses a single fund to satisfy their diversification needs. Other investors may prefer a more sophisticated approach. These investors may want to complement their existing portfolio by exploring a wide range of investment choices. Whether you prefer a simple or sophisticated investment approach, a Capital Vantage variable annuity offers investment choices that can help you meet your goals. Capital Vantage offers funds managed by some of the most respected names in the investment industry. Contract owners will have access to high-caliber managers who offer consistent, quality investment choices across a broad range of investment categories, management styles, and strategies. Capital Vantage provides a diversified spectrum of investment choices. More than 50 funds 12 major investment categories with a range of traditional and nontraditional investment choices Actively managed, riskbased asset allocation portfolios that provide a single-fund solution tailored to meet your risk tolerance 2

Tax-deferred growth potential A variable annuity is a long-term investment designed to help you accumulate assets for retirement on a tax-deferred basis. You generally won t pay income tax on any earnings until you begin taking annuity payments or withdrawals from the contract, and transfers among the investment options in your Capital Vantage variable annuity are tax free. That means more of your contract value remains available to benefit from potential positive market performance. You may also be able to manage your tax liability more efficiently because income tax is deferred during what may be your traditional peak earning years. With a taxable investment, taxes are paid on earnings each year, leaving less money to benefit from investment earnings. THE POWER OF TAX DEFERRAL AND COMPOUNDING Hypothetical growth of $100,000 at a gross 8 percent annual return for 25 years $800,000 $600,000 $400,000 $200,000 $0 $684,848 $521,090 Tax Deferred: Before Tax After Tax $405,542 Taxable This example assumes a 28 percent federal income tax rate and a gross annual growth rate of 8 percent. Note that lower maximum tax rates on capital gains and dividends would make the investment return for the taxable investment more favorable, thereby reducing the difference in performance between the investments shown. Please consider your personal investment horizon and income tax bracket, both current and anticipated, when making an investment decision, as these may further reduce the results of the comparison. This hypothetical example is not intended as a projection of future values and does not represent the performance of any MassMutual product. Deferred variable annuities include mortality and expense risk charges, administrative fees, and, in some cases, sales charges and/or charges for optional benefits, if selected. These charges were not included; if they had been, the tax-deferred performance would have been lower. Taxable withdrawals are subject to ordinary income tax and, if made prior to age 59½, may be subject to an additional 10 percent federal income tax. 3

How Capital Vantage works Choose a share class Capital Vantage has two share classes to choose from: B-Share and C-Share. You must elect one of these options at the time you purchase your contract. Factors such as the fees and expenses associated with each share class, the likelihood of making subsequent purchase payments, and your investment time horizon will help you determine which of the following share classes is right for you. B-Share Class The B-Share class may be more appropriate for the investor who has a longer investment time horizon, who doesn t intend to withdraw contract value that exceeds the free withdrawal amount during the contingent deferred sales charge (CDSC) periods, and who wants a lower-cost contract than the C-Share class. C-Share Class The C-Share class may be more appropriate for the investor who may be likely to make additional purchase payments, who may withdraw contract value after making a purchase payment, and who is willing to pay higher Mortality & Expense (M&E) Risk Charges in return for full access to his or her contract value. Which share class is right for you? Consider both options carefully before you purchase the contract, because once you have selected a share class and the contract is issued, you will not be able to change share classes. 4

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B-Share CDSC schedule The CDSC is a percentage of each purchase payment withdrawn from the contract. The amount of the CDSC charge depends on the length of time between the date that each purchase payment was applied and the date of withdrawal. NUMBER OF FULL YEARS FROM PURCHASE PAYMENT APPLICATION Years 0 1 2 3 4 5+ Percent 7% 7% 6% 5% 4% 0% EXAMPLE OF A FIVE-YEAR ROLLING CDSC SCHEDULE Each time a purchase payment is made, a new CDSC schedule applies. $100,000 Payment $20,000 Payment $20,000 Payment Rolling CDSC Schedule Rolling CDSC Schedule Rolling CDSC Schedule Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7 Year 8 Year 9 Year 10 Contract Years Rolling CDSC schedule The Capital Vantage B-Share class has a rolling CDSC schedule. Each time you make a purchase payment, a new CDSC schedule begins for that purchase payment. If you continue to make purchase payments into your contract, it s possible that you will have to pay a CDSC charge on withdrawals exceeding the free withdrawal amount throughout the life of your contract. M&E Risk and Administrative Charges 1 The M&E Risk and Administrative Charges chart shows the fees and expenses you will pay periodically during the time you own your contract. It does not include underlying fund fees and expenses. The Capital Vantage product and fund prospectuses have more details. B-SHARE CLASS M&E Risk Charge Administrative Charge 0.85% (All years) 0.15% M&E Risk Charge Administrative Charge C-SHARE CLASS 1.30% (0.85% after contract year five.) 0.15% Total 1.00% Total 1.45% (1.00% after contract year five.) 1 M&E Risk and Administrative Charges are shown on an annualized basis, but are deducted daily. 6

Free withdrawal amounts Each contract year, you will have a free withdrawal amount available for withdrawal. (A contract year is based on the anniversary of the date your contract was issued.) The free withdrawal amount is an amount that is not subject to the CDSC. During the first contract year, you may withdraw up to 10 percent of the initial purchase payment applied on the contract issue date without incurring a CDSC. During each subsequent contract year, you may withdraw up to 10 percent of the total purchase payments still subject to a CDSC as of the previous contract anniversary without incurring a CDSC. Times when the CDSC does not apply In some instances, a CDSC will not apply. Exceptions include: Withdrawals of any earnings. Any death benefit payment. When you apply your contract value to any annuity option. This is only a partial list of exceptions. Please refer to the Capital Vantage prospectus for complete details. The amount available for free withdrawal is reduced by any free withdrawal amounts previously taken during that contract year. Any purchase payments made after a contract anniversary in a given contract year will not be included in the calculation of the free withdrawal amount for that same contract year. Unused free withdrawal amounts in any contract year may not be carried over from year to year. Withdrawals of purchase payments that exceed the free withdrawal amount available in each contract year generally are subject to a CDSC. 2 2 Taxable withdrawals are subject to ordinary income tax and, if made prior to age 59½, may be subject to an additional 10 percent federal income tax. Withdrawals may also have a negative impact on the Return of Purchase Payment Death Benefit. 7

Managing your investment over time Capital Vantage provides optional programs designed to help simplify the management of your investments. You can modify timing and amounts to help reach your investment goals. Automatic Rebalancing Program. This program allows you to direct MassMutual to automatically rebalance the contract value allocated to the funds to the original percentage allocations. Rebalancing may occur on a monthly, quarterly, semiannual, or annual basis. Automatic Investment Plan (AIP). The program allows you to periodically transfer funds from an account of your choice for the purpose of making subsequent purchase payments to the contract. Purchase payments can occur on a monthly, quarterly, semiannual, or annual basis. Subsequent purchase payments will be applied to existing allocations for the current tax year. Each subsequent purchase payment for a B-Share will be subject to a new CDSC schedule. Separate Account Dollar-Cost-Averaging Program. You can authorize MassMutual to systematically transfer contract value among selected investment choices. By allocating a smaller amount of assets on a regular schedule rather than larger amounts all at once, you may be less susceptible to the impact of market fluctuations. 3 Consider your legacy options If you die during the accumulation period (before your entire contract value has been applied to an annuity option), Capital Vantage will pay a death benefit. You must elect one of the following death benefit options when you purchase your contract: Contract Value Death Benefit. Your beneficiaries will receive a death benefit equal to your contract value at the time we receive proof of your death and your beneficiary's election of a payment option. Return of Purchase Payment (ROPP) Death Benefit. Your beneficiary will receive an amount equal to the total purchase payments you ve made (adjusted for withdrawals and fees) or the contact value whichever amount is greater at the time we receive the proof of your death and election of a payment option. There is an additional charge for this benefit equal to 0.35 percent of the average daily net asset value of your contract. If you select the ROPP death benefit, your selection of investment options will be limited. The "Investment Selection Approaches" brochure, available from your financial professional, outlines these investment limitations. You can also consult the Capital Vantage prospectus for details. Generally, the maximum issue age for a Capital Vantage contract is age 85. However, for applicants choosing the ROPP death benefit, the maximum issue age is 75. 3 Dollar-cost averaging does not ensure a profit and does not protect you against loss in declining markets. Because dollarcost averaging involves continuous investment in securities regardless of fluctuating price levels of such securities, you should consider your financial ability to continue the program through periods of fluctuating price levels. 8

Managing death benefit proceeds If a death benefit becomes payable, your beneficiary may be able to choose from among several available payment options. These options range from an immediate lump-sum payout to a payout that extends or stretches death benefit proceeds and any tax liability over a beneficiary s life expectancy. 4 A stretch option may help your beneficiary manage death benefit proceeds. The stretch option is also called a nonqualified beneficiary annuity, or a nonqualified stretch. It is designed to provide a beneficiary with an income stream based on his or her life expectancy and offers specific tax advantages. It s important to discuss these options with your tax advisor. Certain death benefit payout options, including stretch payouts, may be limited or unavailable if there are multiple beneficiaries. 4 Life expectancy is determined under the applicable IRS table. 9

Generating a retirement income stream There are two ways to receive a regular income stream from Capital Vantage: through systematic withdrawals or via annuity payments. Systematic withdrawals The Systematic Withdrawal Program (SWP) allows you to set up automatic periodic withdrawals from your contract value. Any withdrawals under this program are taken proportionally from the contract value in your selected investment choices. The SWP allows you to: Receive income on a monthly, quarterly, semiannual, or annual basis ($100 minimum). Start, stop, increase, or decrease withdrawals at any time. 5 For B-Share contracts, you may receive withdrawals up to the free withdrawal amount without incurring a CDSC. Annuity payments Many people nearing or in retirement are concerned about outliving their assets and running out of income. One way to help ensure that you will be able to maintain an income stream is by applying all or a portion of your contract value to fixed annuity payments. In fact, annuity payments are the only income option that can guarantee income for life. 6 Capital Vantage offers a variety of annuity options and features that can be used to customize your income stream. You may choose: Income for one life or two. Guaranteed income for life or for a specific period of time. Legacy protection for your beneficiary. The date annuity payments begin. The frequency of your annuity payments. The annuity phase of your contract begins on the annuity date you choose and ends when the last annuity payment is made. 5 If the SWP is intended to be a series of Substantially Equal Periodic Payments (SEPP) under Internal Revenue Code 72(t)/72(q), making changes to the SWP may be an impermissible modification that will result in prior payments under the SWP becoming subject to an additional 10 percent federal income tax, plus interest. 6 Guarantees are based on the claims-paying ability of the issuing company. 10

Tax-efficient annuity payments If you decide to apply all or a portion of your contract value to an annuity payment, Capital Vantage provides a tax-efficient conversion from the accumulation phase to a guaranteed income stream. If you decide to convert some or all of your contract value into guaranteed income, a portion of each annuity payment you receive will be considered a return of the amount you paid for the annuity (your cost basis) and part will be taxable earnings. This is called the exclusion ratio. The exclusion ratio is the percentage used to calculate each annuity payment s taxable and nontaxable portions. In general, you ll pay ordinary income tax only on the portion of an annuity payment that represents earnings. Once the full cost basis (i.e., the total of all after-tax purchase payments) is returned to you, your annuity payments will be fully taxable. 7 Learn more Your financial professional can answer your questions and help you assess your individual investment needs and goals. 7 If you elect to apply only a portion of your contract value to an annuity option, the cost basis is first allocated on a pro rata basis between the amount applied to the annuity option and the remaining amount of your contract, and the cost basis allocated to the annuitized portion is then used to calculate the exclusion ratio. 11

PRODUCT HIGHLIGHTS Maximum Issue Age (Annuitant/Owner) Purchase Payments 85 (75 with the Return of Purchase Payment Death Benefit) (Age as of last birthday) Initial: $10,000/Subsequent purchase payments $500 minimum Maximum: $1,500,000 (without MassMutual approval) FEES AND CHARGES B-SHARE C-SHARE Mortality & Expense Administrative Total 8 Contingent Deferred Sales Charge (CDSC) 0.85 % 0. 1 5% 1.00% Number of full years from purchase payment application 0 1 2 3 4 5+ 7% 7% 6% 5% 4% 0% A new CDSC schedule applies to each purchase payment 1.30% (Decreases to 0.85% after fifth contract year.) 0. 1 5% 1.45% (Decreases to 1.00% after fifth contract year.) None Access to your full contract value at any time, with no initial sales charge or CDSC Free Withdrawals 9 (Amount available for withdrawals that is not subject to a CDSC) Annual Maintenance Fee (Does not apply to C-Shares) Each contract year, you may withdraw a portion of your contract value free from any surrender charge: During the first contract year, up to 10 percent of the initial purchase payment applied on the contract issue date may be withdrawn without incurring a CDSC. During each subsequent contract year, up to 10 percent of the total purchase payments still subject to a CDSC as of the previous contract anniversary may be withdrawn without incurring a CDSC. Amount available for free withdrawal is reduced by any previous free withdrawal amounts taken during the same contract year. Any purchase payments made after a contract anniversary in a given contract year will not be included in the calculation of the free withdrawal amount for that same contract year. Unused free withdrawal amounts in any contract year may not be carried over from year to year. Withdrawals of purchase payments that exceed the free withdrawal amount available in each contract year generally are subject to a CDSC. $40 Fee is waived for contract values greater than $100,000 when assessed on contract anniversary 8 Charges are deducted daily as a percentage of the daily value of the assets invested in each subaccount. 9 Taxable withdrawals are subject to ordinary income tax and, if made prior to age 59½, may be subject to an additional 10 percent federal income tax. 12

PRODUCT HIGHLIGHTS (continued) Death Benefits (One must be elected at contract issue) Annuity Date Contract Value Death Benefit. Return contract value during accumulation period. Return of Purchase Payment Death Benefit. There is an additional charge for this benefit equal to 0.35 percent of the average daily net asset value of your contract. Provides beneficiaries the greater of the contract value or total purchase payments adjusted for withdrawals. Investment restrictions will apply. Earliest: Five years from contract issue date, except where a lesser period is required by state law Latest: 10th contract anniversary, or the 90th birthday of oldest annuitant or oldest owner (whichever is sooner) Annuity Options Annuitants must be at least 18 on the Annuity Date for the owner to elect a lifecontingent annuity) Single Life Life with Cash Refund Life with Period Certain Period Certain Joint and Survivor Life Life with Period Certain Life and 2/3 Survivor Life and 2/3 Survivor with Period Certain Period Certain Additional Features (Not available with C-Shares) Investment Programs Nursing Home and Hospital Withdrawal Benefit Terminal Illness Withdrawal Benefit Automatic Rebalancing Program: Authorizes MassMutual to periodically rebalance your contract value to the elected allocation percentages. Automatic Investment Plan: Authorizes MassMutual to periodically withdraw funds from an account of your choosing to make purchase payments to your contract. A new CDSC schedule will apply to each additional purchase payment. Minimum additional purchase payment is $100. Separate Account Dollar-Cost-Averaging Program (from a selected fund to any of the other funds): Authorizes MassMutual to systematically transfer contract value among elected investment choices. 10 10 Dollar-cost averaging does not assure a profit and does not protect you against loss in declining markets. Because dollar-cost averaging involves continuous investment in securities regardless of fluctuating price levels of such securities, you should consider your financial ability to continue the program through periods of fluctuating price levels. 13

MassMutual... Helping you secure what matters most. Since 1851, MassMutual has been building a reputation for financial strength and integrity. At MassMutual, we operate for the benefit of our customers. Our business decisions are based on a single guiding principle: to help people secure their future and protect the ones they love. Learn more at www.massmutual.com. This material does not constitute a recommendation to engage in or refrain from a particular course of action. The information within has not been tailored for any individual. The information provided is not written or intended as specific tax or legal advice. MassMutual and its subsidiaries, employees, and representatives are not authorized to give tax or legal advice. Individuals are encouraged to seek advice from their own tax or legal counsel. Before purchasing MassMutual Capital Vantage, you should carefully consider the investment objectives, risks, charges, and expenses of the variable annuity. For this and other information, obtain the MassMutual Capital Vantage prospectus from your registered representative. Please read the prospectus carefully before investing or sending money. You may also obtain the prospectuses (or summary prospectuses, if available) for the annuity s underlying investment choices from your registered representative or online at www.massmutual.com/funds. This product and/or certain features may not be available in all states. MassMutual Capital Vantage (Contract Form #FPVDA15-NVA and ICC15-FPVDA15-NVA in certain states, including North Carolina) is a flexible premium deferred variable annuity contract issued by Massachusetts Mutual Life Insurance Company, Springfield, MA 01111-0001. Variable annuities offered through registered representatives of MML Investors Services, LLC, Springfield, MA 01111-0001 or a broker-dealer that has a selling agreement with MML Strategic Distributors, LLC, Springfield, MA 01111-0001. Principal Underwriters: MML Investors Services, LLC, and MML Strategic Distributors, LLC, subsidiaries of Massachusetts Mutual Life Insurance Company, Springfield, MA 01111-0001. 2018 Massachusetts Mutual Life Insurance Company (MassMutual), Springfield, MA 01111-0001. All rights reserved. www.massmutual.com. AN2600 118 DOL-3 CRN202011-221774