Quarterly Review MassMutual RetireSMART by JPMorgan …

Quarterly Review as of September 30, 2019

MassMutual RetireSMART by JPMorgan Target Date Funds

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Strategy and Objectives

Each MassMutual RetireSMART by JPMorgan Fund seeks to achieve its investment objective by investing in a combination of U.S. domestic and international underlying mutual funds using an asset allocation strategy designed for investors expecting to retire at age 65 around the year designated in the Fund's name and who are likely to stop making new investments in the Fund at or around that time. The Fund's assets are allocated among these underlying mutual funds according to an asset allocation strategy that generally becomes increasingly conservative until it reaches its most conservative strategic target allocations by the end of the year designated in the Fund's name. At that time, the Fund's strategic target allocation will approximate those of the MassMutual RetireSMART by JPMorgan In Retirement Fund.

Portfolio Highlights

Portfolio Managers

Anne Lester J.P. Morgan 27 years industry experience Daniel Oldroyd, CFA, CAIA J.P. Morgan 20 years industry experience

Rick Schulitz, CFA, CAIA MML Investment Advisers LLC 16 years industry experience

The MassMutual RetireSMART by JPMorgan Retirement Funds delivered positive absolute and relative performance for the quarter. Nine of the ten Funds in the series outperformed their respective Morningstar categories during the period. The following drove performance relative to peers for the quarter: ? Tactical asset allocation provided the greatest contribution to excess return versus peers. Overweight allocations to real

estate investment trusts (REITs) and U.S. large-cap equity drove results. ? The glide path was additive, as the strategic mix of asset classes aided results. Higher exposure to REITs contributed

along with other favorable positioning. ? Manager selection results, as measured by performance of underlying funds relative to their respective benchmarks,

detracted modestly.

Performance Detail

Market Context Trade war related concerns of a global economic slowdown weighed on investors as they tried to balance strong U.S. consumption, a rebound in U.S. housing, and renewed monetary stimulus from a majority of the world's central banks. The temporary inversion of the U.S. yield curve troubled investors. Inversions of the yield curve occur when short-term rates rise higher than long-term rates. Historically, such inversions sometimes preceded economic contractions. An economic slowdown in China and Europe led the Organization for Economic Co-operation and Development (OECD) to lower its 2019 global growth forecast from 3.2% to 2.9%. This is the slowest pace since the global financial crisis. Global stocks delivered mixed performance as slowing global growth and renewed concerns over trade weighed on investors. Despite rate cuts by the FOMC in July and September, the U.S. dollar climbed higher and helped U.S. stocks beat international stocks for the quarter. Emerging market stocks continued to trail their developed market brethren, as investors remained concerned over the impact of the ongoing trade war on exporters. U.S. bonds, especially longer duration bonds, had another strong quarter as the expectations for lower global growth and easing global monetary policy drove interest rates lower. Glide Path Decision Effects ? The Fund's higher strategic allocation to real estate investment trusts (REITs) and heavier exposure to fixed income

relative peers was positive. ? Lower strategic allocations to U.S. large-cap equity and higher exposure to emerging market equities detracted from

performance.

Manager Selection Effects ? Manager selection results, as measured by performance of underlying funds relative to their respective benchmarks,

detracted modestly. Several underlying equity funds underperformed their respective benchmarks. These included the MassMutual Select Blue Chip Growth Fund and MM Select Equity Asset Fund. However, the MassMutual Select Strategic Bond Fund and MassMutual Premier High Yield Fund delivered strong benchmark-relative performance. Tactical Asset Allocation Effects ? Portfolio manager decisions on asset-class allocation biases and rebalances contributed strongly to quarterly results. ? The decision to go overweight to REITs and U.S. large-cap equity and to go underweight to emerging market equity, international developed equity, and U.S. small cap equity was rewarded. ? An underweight to core fixed income detracted.

Manager Outlook

Throughout the third quarter, Fund management maintained a modest underweight to total equities but continued to favor U.S. large-cap equities, noting the S&P 500? Index's more resilient and higher-quality earnings data relative to other equity markets. Fund management retained a defensive overweight allocation to cash, closed an underweight position in core fixed income, and added an overweight position to REITs, maintaining their cautious bias given the elevated tail risks in the current market environment.

MassMutual RetireSMART by JPMorgan Target Date Funds

As of September 30, 2019

I SHARE CLASS

MassMutual RetireSMART by JPMorgan Funds Strategic Glide Path

100%

90%

80%

% of Portfolio Allocation

70%

60%

50%

40%

30%

20%

10%

0%

40

35

30

Asset Allocation Percentages

Asset Class

Fixed Income Money Market Intermediate Term Bond High Yield Bond Emerging Market Bond Inflation Protected Bond

Equity U.S. Large Cap Equity U.S. Mid Cap Equity U.S. Small Cap Equity U.S. REITS International Equity Emerging Markets Equity

Cash & Cash Alternatives

TIPS

Core Fixed Income

High Yield

Emerging Market Debt

REITs

Emerging Equity

EAFE

U.S. Small/Mid Cap

U.S. Large Cap

25

20

15

10

5

0

-5

-10

In Ret

69.41% 6.49% 41.65% 9.99% 3.75% 7.53% 30.59% 15.04% 1.95% 0.55% 3.02% 8.08% 1.94%

2020

63.06% 4.50% 40.44% 8.88% 3.53% 5.72% 36.94% 17.84% 2.34% 0.81% 3.42% 9.97% 2.57%

MassMutual RetireSMART by JPMorgan Fund Date

2025

2030

2035

2040

2045

2050

48.53% 1.50% 35.88% 6.30% 3.04% 1.81% 51.47% 24.25% 3.21% 1.38% 4.33% 14.31% 3.99%

36.20% 1.50% 27.83% 4.38% 2.48% 0.00% 63.80% 29.71% 3.96% 1.86% 5.09% 17.99% 5.21%

26.30% 1.51% 18.80% 4.19% 1.81% 0.00% 73.70% 35.45% 4.63% 2.04% 5.79% 20.23% 5.55%

17.19% 1.51% 10.89% 3.49% 1.29% 0.00% 82.81% 39.46% 5.19% 2.41% 6.37% 22.96% 6.43%

11.70% 1.51% 6.25% 2.98% 0.96% 0.00% 88.30% 41.88% 5.52% 2.64% 6.70% 24.58% 6.98%

11.70% 1.51% 6.25% 2.98% 0.96% 0.00% 88.30% 41.93% 5.51% 2.63% 6.67% 24.61% 6.96%

2055

11.70% 1.51% 6.26% 2.97% 0.96% 0.00% 88.30% 42.01% 5.49% 2.62% 6.63% 24.64% 6.93%

2060

11.70% 1.51% 6.27% 2.97% 0.96% 0.00% 88.30% 41.95% 5.50% 2.62% 6.66% 24.61% 6.95%

Generally target retirement date (lifecycle) investment options are designed to be held beyond the presumed retirement date to offer a continuing investment option for the investor in retirement. The year in the investment option name refers to the approximate year an investor in the option would plan to retire and likely would stop making new contributions to the investment option. However, investors may choose a date other than their presumed retirement date to be more conservative or aggressive depending on their own risk tolerance. Target retirement date (lifecycle) investment options are designed for participants who plan to withdraw the value of their accounts gradually after retirement. Each of these options follows its own asset allocation path ("glide path") to progressively reduce its equity exposure and become more conservative over time. Options may not reach their most conservative allocation until after their target date. Others may reach their most conservative allocation in their target date year. Investors should consider their own personal risk tolerance, circumstances and financial situation. These options should not be selected solely on a single factor such as age or retirement date. Please consult the prospectus (if applicable) pertaining to the options to determine if their glide path is consistent with your long-term financial plan. Target retirement date investment options' stated asset allocation may be subject to change. Investments in these options are not guaranteed and you may experience losses, including losses near, at, or after the target date. Additionally, there is no guarantee that the options will provide adequate income at and through retirement .

These materials and the platform of investments made available by MassMutual are offered without regard to the individualized needs of any plan, its participants, or beneficiaries. These materials are not intended as impartial investment advice or to give advice in a fiduciary capacity to any plan. The Fund's Principal Risks include risks such as Allocation Risk, Bank Loans Risk, Below Investment Grade Risk, Cash Position Risk, Commodities-Related Investment Risk, Convertible Securities Risk, and others. Please refer to the prospectus or summary prospectus for a complete listing of the Fund's principal risks and more information on each of the those risks. Copies of each Fund's prospectus can be obtained by visiting of by sending an email to fundinfo@.

Investors should consider an investment option's objectives, risks, fees, and expenses carefully before investing. This and other information can be found in the applicable prospectuses or summary prospectuses, which are available from MassMutual by visiting or by calling 1-866-444-2601. Please read them carefully before investing. MassMutual has hired J.P. Morgan Investment Management Inc. as subaviser to the funds. J.P. Morgan Asset Management is the marketing name for the asset management businesses of JPMorgan Chase & Co. and its affiliates worldwide. ? 2019 Massachusetts Mutual Life Insurance Company (MassMutual?), Springfield, MA. All rights reserved. Principal Underwriter: MML Distributors, LLC. (MMLD) Member FINRA and SIPC ( and ), 100 Bright Meadow Blvd., Enfield, CT 06082. MMLD is a subsidiary of Massachusetts Mutual Life Insurance Company. Investment advisory services provided to the Funds by MML Investment Advisers, LLC.

NOT FDIC INSURED MAY LOSE VALUE NO BANK GUARANTEE

RS-41578-11

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