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Investment Option Performance Data as of: 8/1/2018 The investment funds in this Investment Option Performance Report reflect the investment options currently offered under your plan. MassMutual has not determined or made any recommendations as to which investment options are to be offered under your plan. MassMutual organizes the investment funds available to retirement plans on its recordkeeping platform into several different Investment Menus which generally group funds by similar fund expenses and financial professional compensation. The Investment Menus generally include any funds for which we have trading arrangements for Plan clients and were not created to take into account any financial and investment objectives, risk tolerance or the suitability of any investment option with respect to any specific client. For more information on the investment funds offered under your plan, including the rates of compensation paid to MassMutual from the investment funds or their affiliates, please review the applicable Investment Menus and each fund's prospectus. Please contact your financial professional or team at MassMutual for a copy of the Investment Menus. Please note that MassMutual and its affiliates, subsidiaries or service providers do not offer investment advice and do not act as plan fiduciaries. The selection and monitoring of investments for the plan remains the sole responsibility of the plan fiduciary, which shall in no instance be MassMutual or any of its affiliates, subsidiaries, service providers or employees. Performance data shown represents past performance and is no guarantee of future results. Investment return and principal value fluctuate so your shares, when sold, may be worth more or less than the original cost; current performance may be lower or higher than quoted. For more recent performance, call or visit each fund company's Web site. Morningstar Objective Ratio ** (NAV) Return (NAV) Morningstar Percentile ing*** Yr 5 Yr Asset Allocation Allocation--0% to 50% Equity MFS Conservative Allocation R4 04/01/05 N 0.68/0.68 2.27 2.66 5.64 6.4 5.71 6.27 21 107 0 120 0 112 21 47 897 Participant(s) with Balance / $14,018,410.42 in Plan Assets Morningstar Mod Con Tgt Risk TR USD 1.94 1.47 4.81 6.8 5.46 5.52 Total Number of s in Category Allocation--0% to 50% Equity: 510 45 55 256 Allocation--50% to 70% Equity MFS Moderate Allocation R4 04/01/05 N 0.7/0.7.20 4.19 8.86 8.56 7.46 7.21 8 266 8 257 51 16 7 151 592 Participant(s) with Balance / $18,49,762.21 in Plan Assets Morningstar Mod Tgt Risk TR USD 2.48 2.1 7.6 8.56 7.17 6.65 Total Number of s in Category Allocation--50% to 70% Equity: 762 704 620 44 Allocation--70% to 85% Equity MFS Growth Allocation R4 04/01/05 N 0.80/0.79.9 5.70 12.07 10.82 9.15 7.94 25 47 24 54 5 75 18 26 690 Participant(s) with Balance / $10,596,671.44 in Plan Assets Morningstar Mod Agg Tgt Risk TR USD.08.0 10.19 10.77 8.86 7.54 CULLEN/FROST 401(K) PLAN 1

Table of Contents 1. CLIENT DATA Pages Investment Option Performance Quarterly Investment Option Performance 1 6 CULLEN/FROST 401(K) PLAN

(NAV) Return (NAV) Morningstar Percentile ing*** Morningstar Objective Yr 5 Yr Ratio ** Asset Allocation Total Number of s in Category Allocation--70% to 85% Equity: 49 2 279 201 Cash Money Market-Taxable Invesco Shrt-Trm Inv Treasury Instl 04/12/84 N 0.20/0.18 0.45 1.05 1.8 0.68 0.42 0.26 N/A 7 N/A 8 N/A 2 N/A 6 798 Participant(s) with Balance / $45,054,08. in Plan Assets ICE BofAML USD M Dep OR CM TR USD 0.59 1.2 1.72 1.05 0.7 0.7 Total Number of s in Category Money Market-Taxable: 52 461 40 6 Bonds Inflation-Protected Bond PIMCO Real Return Instl 01/29/97 N 0.88/0.88 0.76-0.20 0.57 2.22 1.8. 59 119 20 46 20 25 5 4 451 Participant(s) with Balance / $4,70,768.4 in Plan Assets BBgBarc US Treasury US TIPS TR USD 0.64 0.21 0.8 2.20 1.88.0 Total Number of s in Category Inflation-Protected Bond: 25 206 174 107 Short-Term Bond Frost Low Duration Bond - I 04/25/08 N 0.46/0.46 0.49 0.86 0.84 1.7 1.7 2.84 25 117 46 188 44 145 2 56 522 Participant(s) with Balance / $9,589,60.74 in Plan Assets Frost Bond - I 04/25/08 N 0.51/0.51 0.88 1.24 1.2.41.64 6.0 9 7 4 12 1 1 1 1,010 Participant(s) with Balance / $29,448,814.45 in Plan Assets BBgBarc US Govt/Credit 1-5 Yr TR USD 0.45 0.14-0.4 0.95 1.21 2.20 Total Number of s in Category Short-Term Bond: 524 467 90 260 Balanced Allocation--50% to 70% Equity American s Amer Balanced R6 05/01/09 N 0.28/0.28.80 4.14 10.22 11.00 10.19 8.97 24 16 4 2 4 19 4 N/A 802 Participant(s) with Balance / $1,147,415.04 in Plan Assets Morningstar Mod Tgt Risk TR USD 2.48 2.1 7.6 8.56 7.17 6.65 Total Number of s in Category Allocation--50% to 70% Equity: 762 704 620 44 Large Blend Vanguard Institutional Index Instl 07/1/90 N 0.0/0.0 7.75 9.91 19.62 16.08 14.49 10.86 29 4 10 92 10 8 18 117 1,168 Participant(s) with Balance / $7,918,855.1 in Plan Assets Russell 1000 TR USD 7.71 10.07 19.82 15.84 14.6 10.9 Total Number of s in Category Large Blend: 168 1184 1059 784 CULLEN/FROST 401(K) PLAN 2

Morningstar Objective Ratio ** (NAV) Return (NAV) Morningstar Percentile ing*** Yr 5 Yr Large Growth American s AMCAP R6 05/01/09 N 0.6/0.6 5.0 1.18 2.9 15.8 14.57 12.1 54 749 66 851 62 702 1 N/A 1,206 Participant(s) with Balance / $1,172,70.65 in Plan Assets Frost Growth Equity I 04/25/08 N 0.64/0.64 8.29 19.94 29.87 18.42 16.67 11.5 1 186 27 289 1 27 47 79 1,081 Participant(s) with Balance / $29,529,61.44 in Plan Assets Russell 1000 Growth TR USD 9.61 16.44 27.2 19. 17.47 12.84 Total Number of s in Category Large Growth: 1427 1251 1124 812 Large Value Frost Value Equity Inst 04/25/08 N 0.65/0.65.04 2.57 12.06 10.45 11.16 8.7 7 880 8 886 41 5 6 41 561 Participant(s) with Balance / $8,091,90.91 in Plan Assets MFS Value R6 05/01/06 N 0.49/0.49 5.77 1.65 9.81 12.12 11.54 9.16 91 1150 55 549 2 254 41 242 851 Participant(s) with Balance / $21,540,70.27 in Plan Assets Russell 1000 Value TR USD 5.76.71 12.47 12.2 11.22 8.9 Total Number of s in Category Large Value: 127 1109 956 701 Mid-Cap Blend JHancock Disciplined Value Mid Cap R6 09/01/11 N 0.77/0.76.48.4 12.58 12.27 1.19 12.67 8 62 50 151 10 2 2 N/A 1,059 Participant(s) with Balance / $17,94,5.66 in Plan Assets Russell Mid Cap TR USD 6.40 8.15 17.89 1.7 12.80 10.92 Total Number of s in Category Mid-Cap Blend: 457 66 229 Mid-Cap Growth T. Rowe Price Mid-Cap Growth I 08/28/15 N 0.62/0.62 7.62 12.71 20.21 15.12 15.48 1.08 75 445 8 195 11 N/A 5 N/A 1,280 Participant(s) with Balance / $25,24,098.89 in Plan Assets Russell Mid Cap Growth TR USD 8.45 1.87 25.06 15.29 14.19 11.64 Total Number of s in Category Mid-Cap Growth: 602 58 478 4 Real Estate Invesco Real Estate - R6 09/24/12 N 0.80/0.80 6.78.7 6.08 9.4 10.25 7.09 47 94 2 51 7 54 59 N/A 582 Participant(s) with Balance / $6,547,242.15 in Plan Assets SP United States REIT TR USD 8.1 5.1 6.86 9.54 10.28 7.67 Total Number of s in Category Real Estate: 250 222 190 18 Small Blend Vanguard Small Cap Index Inst 07/07/97 N 0.04/0.04 7.18 12.78 2.77 15.17 1.08 11.46 7 287 4 209 21 117 16 56 1,078 Participant(s) with Balance / $17,259,119. in Plan Assets CULLEN/FROST 401(K) PLAN

(NAV) Return (NAV) Morningstar Percentile ing*** Morningstar Objective Yr 5 Yr Ratio ** Russell 2000 TR USD 6.89 14.26 25.45 16.11 1.00 10.46 Total Number of s in Category Small Blend: 781 645 54 88 Small Value Victory Sycamore Small Company Opp I 08/1/07 N 0.90/0.90 6.6 9.95 22.68 16.72 14.62 11.28 22 66 12 29 2 4 9 17 55 Participant(s) with Balance / $7,095,905.9 in Plan Assets Russell 2000 Value TR USD 4.82 9.86 20.05 15.7 11.72 9.27 Total Number of s in Category Small Value: 416 61 17 225 Global/ International Diversified Emerging Mkts Aberdeen Emerging Markets Instl 05/11/07 N 1.1/1.10-4.06-10.59-7.44 8.08.24 5.59 90 748 71 490 71 67 9 1 702 Participant(s) with Balance / $6,905,789.5 in Plan Assets MSCI EM NR USD -4.70-7.18-0.68 11.42 5.04.45 Total Number of s in Category Diversified Emerging Mkts: 86 695 500 209 Foreign Large Blend Lazard International Equity R6 04/01/15 N 0.81/0.80-1.71 -.07.21 4.0 4.96 4.68 51 16 96 607 66 N/A 19 N/A 1,0 Participant(s) with Balance / $20,272,88.74 in Plan Assets MSCI ACWI Ex USA NR USD -1.64 -.5.18 8.08 5.4.44 Total Number of s in Category Foreign Large Blend: 776 68 54 7 Other Other Cullen Frost Stock 01/01/02 N N/A -2.88 16.78 0.98 19.2 9.15 7. N/A N/A N/A N/A N/A N/A N/A N/A,949 Participant(s) with Balance / $24,052,998.21 in Plan Assets Total Number of s in Category Other: N/A N/A N/A N/A This Investment Option Performance report must be accompanied by the most recent quarter end performance when not created for a quarter end time period. Performance results reflect any applicable expense subsidies and waivers in effect during the periods shown. Without such subsidies and waivers the fund's performance results would be less favorable. The performance is as of the date shown; it may not include the fund's entire investment portfolio and is subject to change. Other share classes may be available for which performance and expenses will differ. The Cullen/Frost Stock commenced investment operations on November 2, 2009. Performance of this Stock prior to November 2, 2009 reflects the performance of the Cullen/Frost Bankers, Inc. Common Stock. In addition, effective November 2, 2009, an approximate 2% cash ratio was introduced to the Stock. As a result, performance of the Stock since November 2, 2009 reflects approximately 2% cash and 98% of the common stock. CULLEN/FROST 401(K) PLAN 4

*Redemption Fees ( Fee) - MassMutual facilitates the imposition and collection of redemption fees for mutual funds on its recordkeeping system with certain restrictions. Certain mutual funds impose redemption fees on short-term trading activity that the funds deem to be harmful to long-term shareholders. A "Y" indicates that MassMutual collects and remits redemption fees for such fund in accordance with an agreement, directly or indirectly, with the fund. Redemption fees are generally only imposed on participant initiated exchanges under such agreements. An "N" indicates that MassMutual currently does not collect and remit redemption fees for such fund. The list of funds for which MassMutual imposes redemption fees is subject to change at any time. Please review the terms of the fund's prospectus for information on the time periods and fee amounts associated with the fund's redemption fee. **Gross Ratio is the fund's total operating expense ratio reflected in the fund's most recent prospectus. Net Ratio reflects a fund's Gross Ratio reduced by any voluntary and/or contractual expense reductions being applied to the fund. For more expense ratio information, including applicable fee reduction expiration dates, please consult the fund's expense table in the prospectus. ***The Morningstar Percentile ing compares a 's Morningstar risk and return scores with all the s in the same Category, where 1% = Best and 100% = Worst. Morningstar / Total Number of s in Category displays the fund's actual rank within its Morningstar Category based on average annual total return and number of s in that Category. 2016 Morningstar, Inc. All Rights Reserved. The information contained herein: (1) is proprietary to Morningstar and/or its content providers; (2) may not be copied or distributed; and () is not warranted to be accurate, complete, or timely. Neither Morningstar nor its content providers are responsible for any damages or losses arising from any use of this information. Past performance is no guarantee of future results. Please review the terms of the applicable fund's prospectus for more detail on the fees paid by the fund. Important Risk Notes Asset Allocation--Performance of Asset Allocation s depends on the underlying mutual funds in which they invest. These funds are subject to the volatility of the financial markets in the U.S. and abroad and may be subject to the additional risks associated with investing in high yield, small cap and foreign securities. Bonds--Although bonds generally present less short-term risk and volatility than stocks, bonds do contain interest rate risk (as interest rates rise, bond prices usually fall and vice versa) and the risk of default, or the risk that an issuer will be unable to make income or principal payments. Additionally, bonds and short-term investments entail greater inflation risk, or the risk that the return of an investment will not keep up with increases in the prices of goods and services, than stocks. High Yield Bond--s that invest in lower-quality securities generally offer higher yields, but also carry more risk. Global/International Stocks--Foreign investments involve greater risks than U.S. investments, including political and economic risks and the risk of currency fluctuations, all of which may be magnified in emerging markets. Mid Cap--Investments in mid-sized companies may involve greater risks than those in larger, more well known companies, but may be less volatile than investments in smaller companies. Sector/Specialty--s with a narrow focus tend to be more volatile than funds that diversify across many sectors and companies. Small Cap--Investments in smaller companies may involve greater risks than those in larger, better known companies. Balanced/--Stock values fluctuate in response to the activities of individual companies and general market and economic conditions. Value--Investments in stocks can perform differently from the market as a whole. They can remain undervalued by the market for long periods of time. data was obtained from a third party mutual fund analytical firm. Although the data is gathered from a third party source believed to be reliable, MassMutual and its affiliates cannot guarantee the accuracy and/or completeness of the information. Money market funds are not insured or guaranteed by The Federal Deposit Insurance Corporation (FDIC) or any other government agency. Although the funds seek to preserve the value of the investment at $1.00 per share, it is possible to lose money by investing in the funds. Investors should consider an investment's objectives, risks, charges and expenses carefully before investing. For this and other information, see the prospectus available from MassMutual. Read them carefully. 2017 Massachusetts Mutual Life Insurance Company (MassMutual), Springfield, MA 01111-0001. All rights reserved. www.massmutual.com. CULLEN/FROST 401(K) PLAN 5

Quarterly Investment Option Performance Data as of: 6/29/2018 The investment funds in this Investment Option Performance Report reflect the investment options currently offered under your plan. MassMutual has not determined or made any recommendations as to which investment options are to be offered under your plan. MassMutual organizes the investment funds available to retirement plans on its recordkeeping platform into several different Investment Menus which generally group funds by similar fund expenses and financial professional compensation. The Investment Menus generally include any funds for which we have trading arrangements for Plan clients and were not created to take into account any financial and investment objectives, risk tolerance or the suitability of any investment option with respect to any specific client. For more information on the investment funds offered under your plan, including the rates of compensation paid to MassMutual from the investment funds or their affiliates, please review the applicable Investment Menus and each fund's prospectus. Please contact your financial professional or team at MassMutual for a copy of the Investment Menus. Please note that MassMutual and its affiliates, subsidiaries or service providers do not offer investment advice and do not act as plan fiduciaries. The selection and monitoring of investments for the plan remains the sole responsibility of the plan fiduciary, which shall in no instance be MassMutual or any of its affiliates, subsidiaries, service providers or employees. Performance data shown represents past performance and is no guarantee of future results. Investment return and principal value fluctuate so your shares, when sold, may be worth more or less than the original cost; current performance may be lower or higher than quoted. For more recent performance, call or visit each fund company's Web site. Morningstar Objective Ratio ** (NAV) Return (NAV) Morningstar Percentile ing*** Yr 5 Yr Asset Allocation Allocation--0% to 50% Equity MFS Conservative Allocation R4 04/01/05 N 0.68/0.68 0.78 0.58 5.25 4.97 5.46 6.04 22 107 21 9 29 105 18 40 897 Participant(s) with Balance / $14,018,410.42 in Plan Assets Morningstar Mod Con Tgt Risk TR USD 0.9-0.5 4.68 4.98 5.2 5.27 Total Number of s in Category Allocation--0% to 50% Equity: 517 425 58 255 Allocation--50% to 70% Equity MFS Moderate Allocation R4 04/01/05 N 0.7/0.7 1.5 1.6 7.91 6.56 7.20 6.82 26 192 27 18 47 295 8 144 592 Participant(s) with Balance / $18,49,762.21 in Plan Assets Morningstar Mod Tgt Risk TR USD 0.56-0.1 6.92 6.41 6.92 6.28 Total Number of s in Category Allocation--50% to 70% Equity: 766 674 617 49 Allocation--70% to 85% Equity MFS Growth Allocation R4 04/01/05 N 0.80/0.79 1.85 2.15 10.5 8.19 8.87 7.6 19 5 12 29 65 18 25 690 Participant(s) with Balance / $10,596,671.44 in Plan Assets Morningstar Mod Agg Tgt Risk TR USD 0.76-0.0 9. 7.82 8.60 7.06 CULLEN/FROST 401(K) PLAN 6

Morningstar Objective Ratio ** (NAV) Return (NAV) Morningstar Percentile ing*** Yr 5 Yr Asset Allocation Total Number of s in Category Allocation--70% to 85% Equity: 44 1 274 199 Cash Money Market-Taxable Invesco Shrt-Trm Inv Treasury Instl 04/12/84 N 0.20/0.18 0.41 0.74 1.22 0.58 0.6 0.27 N/A 42 N/A 40 N/A N/A 57 798 Participant(s) with Balance / $45,054,08. in Plan Assets ICE BofAML USD M Dep OR CM TR USD 0.58 0.91 1.5 0.9 0.66 0.7 Total Number of s in Category Money Market-Taxable: 524 452 427 59 Bonds Inflation-Protected Bond PIMCO Real Return Instl 01/29/97 N 0.64/0.45 0.77-0.25 2.05 1.97 1.64.6 6 75 15 5 18 25 5 4 451 Participant(s) with Balance / $4,70,768.4 in Plan Assets BBgBarc US Treasury US TIPS TR USD 0.77-0.02 2.11 1.9 1.68.0 Total Number of s in Category Inflation-Protected Bond: 28 211 177 112 Short-Term Bond Frost Low Duration Bond - I 04/25/08 N 0.46/0.46 0.28 0.42 1.12 1.22 1.26 2.82 14 6 4 165 47 151 22 51 522 Participant(s) with Balance / $9,589,60.74 in Plan Assets Frost Bond - I 04/25/08 N 0.51/0.51 0.56 0.47 1.90.06.49 5.88 6 21 9 1 1 1 1,010 Participant(s) with Balance / $29,448,814.45 in Plan Assets BBgBarc US Govt/Credit 1-5 Yr TR USD 0.17-0. -0.20 0.84 1.1 2.24 Total Number of s in Category Short-Term Bond: 51 447 78 250 Balanced Allocation--50% to 70% Equity American s Amer Balanced R6 05/01/09 N 0.28/0.28 2.19 1.01 9.5 8.94 9.66 8.7 9 57 2 7 16 N/A 802 Participant(s) with Balance / $1,147,415.04 in Plan Assets Morningstar Mod Tgt Risk TR USD 0.56-0.1 6.92 6.41 6.92 6.28 Total Number of s in Category Allocation--50% to 70% Equity: 766 674 617 49 Large Blend Vanguard Institutional Index Instl 07/1/90 N 0.0/0.0.42 2.6 14. 11.90 1.9 10.17 28 61 11 96 11 100 18 114 1,168 Participant(s) with Balance / $7,918,855.1 in Plan Assets Russell 1000 TR USD.57 2.85 14.54 11.64 1.7 10.20 CULLEN/FROST 401(K) PLAN 7

Morningstar Objective Ratio ** (NAV) Return (NAV) Morningstar Percentile ing*** Yr 5 Yr Total Number of s in Category Large Blend: 15 1166 1042 776 Large Growth American s AMCAP R6 05/01/09 N 0.6/0.6 5.01 8.57 21.70 12.05 14.75 11.88 4 647 56 726 50 575 20 N/A 1,206 Participant(s) with Balance / $1,172,70.65 in Plan Assets Frost Growth Equity I 04/25/08 N 0.64/0.64 6.7 11.6 25.50 14.4 15.90 10.07 21 15 26 294 1 40 56 469 1,081 Participant(s) with Balance / $29,529,61.44 in Plan Assets Russell 1000 Growth TR USD 5.76 7.25 22.51 14.98 16.6 11.8 Total Number of s in Category Large Growth: 1454 1265 1141 825 Large Value Frost Value Equity Inst 04/25/08 N 0.65/0.65 1.0-0.95 8.85 7.89 10.92 7.81 52 584 61 64 27 198 66 417 561 Participant(s) with Balance / $8,091,90.91 in Plan Assets MFS Value R6 05/01/06 N 0.49/0.49-0.56 -.55 4.1 8.48 10.78 8.69 95 1194 51 492 0 26 9 27 851 Participant(s) with Balance / $21,540,70.27 in Plan Assets Russell 1000 Value TR USD 1.18-1.69 6.77 8.26 10.4 8.49 Total Number of s in Category Large Value: 127 1099 951 686 Mid-Cap Blend JHancock Disciplined Value Mid Cap R6 09/01/11 N 0.77/0.77-0.69-1.0 7.6 9.47 12.87 12.59 85 47 9 111 8 20 1 N/A 1,059 Participant(s) with Balance / $17,94,5.66 in Plan Assets Russell Mid Cap TR USD 2.82 2.5 12. 9.58 12.22 10.2 Total Number of s in Category Mid-Cap Blend: 456 69 29 22 Mid-Cap Growth T. Rowe Price Mid-Cap Growth I 08/28/15 N 0.62/0.62 0.94 5.07 14.5 11.7 14.97 12.07 75 447 26 N/A 10 N/A 6 N/A 1,280 Participant(s) with Balance / $25,24,098.89 in Plan Assets Russell Mid Cap Growth TR USD.16 5.40 18.52 10.7 1.7 10.45 Total Number of s in Category Mid-Cap Growth: 607 541 480 44 Real Estate Invesco Real Estate - R6 09/24/12 N 0.80/0.80 7.01 0.98 5.18 8.1 8.45 7.19 14 8 25 46 28 42 60 N/A 582 Participant(s) with Balance / $6,547,242.15 in Plan Assets SP United States REIT TR USD 10.7 1.7.62 7.81 8.08 7.82 Total Number of s in Category Real Estate: 259 20 199 14 Small Blend Vanguard Small Cap Index Inst 07/07/97 N 0.04/0.04 6.21 5.99 16.51 10.47 12.41 11.29 6 260 6 207 26 18 18 64 CULLEN/FROST 401(K) PLAN 8

Morningstar Objective Ratio ** (NAV) Return (NAV) Morningstar Percentile ing*** Yr 5 Yr Small Blend 1,078 Participant(s) with Balance / $17,259,119. in Plan Assets Russell 2000 TR USD 7.75 7.66 17.57 10.96 12.46 10.60 Total Number of s in Category Small Blend: 775 69 59 9 Small Value Victory Sycamore Small Company Opp I 08/1/07 N 0.90/0.90 4.85.69 14.59 1.47 1.78 11.40 25 80 5 10 2 4 18 28 55 Participant(s) with Balance / $7,095,905.9 in Plan Assets Russell 2000 Value TR USD 8.0 5.44 1.10 11.22 11.18 9.88 Total Number of s in Category Small Value: 41 58 16 220 Global/ International Other Diversified Emerging Mkts Aberdeen Emerging Markets Instl 05/11/07 N 1.1/1.10-11.08-11.0-2.65.41 2.09 5.06 95 782 74 508 8 416 7 9 702 Participant(s) with Balance / $6,905,789.5 in Plan Assets MSCI EM NR USD -7.96-6.66 8.20 5.60 5.01 2.26 Total Number of s in Category Diversified Emerging Mkts: 82 688 489 20 Foreign Large Blend Lazard International Equity R6 04/01/15 N 0.81/0.80-2.51-2.71 6.55 2.55 5.54 4.06 46 292 89 59 67 N/A 15 N/A 1,0 Participant(s) with Balance / $20,272,88.74 in Plan Assets MSCI ACWI Ex USA NR USD -2.61 -.77 7.28 5.07 5.99 2.54 Total Number of s in Category Foreign Large Blend: 774 62 5 71 Other Cullen Frost Stock 06/0/0 N N/A 2.04 14.07 14.97 11.01 9.92 7.89 N/A N/A N/A N/A N/A N/A N/A N/A,949 Participant(s) with Balance / $24,052,998.21 in Plan Assets Total Number of s in Category Other: N/A N/A N/A N/A Performance results reflect any applicable expense subsidies and waivers in effect during the periods shown. Without such subsidies and waivers the fund's performance results would be less favorable. The performance is as of the date shown; it may not include the fund's entire investment portfolio and is subject to change. Other share classes may be available for which performance and expenses will differ. The Cullen/Frost Stock commenced investment operations on November 2, 2009. Performance of this Stock prior to November 2, 2009 reflects the performance of the Cullen/Frost Bankers, Inc. Common Stock. In addition, effective November 2, 2009, an approximate 2% cash ratio was introduced to the Stock. As a result, performance of the Stock since November 2, 2009 reflects approximately 2% cash and 98% of the common stock. CULLEN/FROST 401(K) PLAN 9

*Redemption Fees ( Fee) - MassMutual facilitates the imposition and collection of redemption fees for mutual funds on its recordkeeping system with certain restrictions. Certain mutual funds impose redemption fees on short-term trading activity that the funds deem to be harmful to long-term shareholders. A "Y" indicates that MassMutual collects and remits redemption fees for such fund in accordance with an agreement, directly or indirectly, with the fund. Redemption fees are generally only imposed on participant initiated exchanges under such agreements. An "N" indicates that MassMutual currently does not collect and remit redemption fees for such fund. The list of funds for which MassMutual imposes redemption fees is subject to change at any time. Please review the terms of the fund's prospectus for information on the time periods and fee amounts associated with the fund's redemption fee. **Gross Ratio is the fund's total operating expense ratio reflected in the fund's most recent prospectus. Net Ratio reflects a fund's Gross Ratio reduced by any voluntary and/or contractual expense reductions being applied to the fund. For more expense ratio information, including applicable fee reduction expiration dates, please consult the fund's expense table in the prospectus. ***The Morningstar Percentile ing compares a 's Morningstar risk and return scores with all the s in the same Category, where 1% = Best and 100% = Worst. Morningstar / Total Number of s in Category displays the fund's actual rank within its Morningstar Category based on average annual total return and number of s in that Category. 2016 Morningstar, Inc. All Rights Reserved. The information contained herein: (1) is proprietary to Morningstar and/or its content providers; (2) may not be copied or distributed; and () is not warranted to be accurate, complete, or timely. Neither Morningstar nor its content providers are responsible for any damages or losses arising from any use of this information. Past performance is no guarantee of future results. Please review the terms of the applicable fund's prospectus for more detail on the fees paid by the fund. Important Risk Notes Asset Allocation--Performance of Asset Allocation s depends on the underlying mutual funds in which they invest. These funds are subject to the volatility of the financial markets in the U.S. and abroad and may be subject to the additional risks associated with investing in high yield, small cap and foreign securities. Bonds--Although bonds generally present less short-term risk and volatility than stocks, bonds do contain interest rate risk (as interest rates rise, bond prices usually fall and vice versa) and the risk of default, or the risk that an issuer will be unable to make income or principal payments. Additionally, bonds and short-term investments entail greater inflation risk, or the risk that the return of an investment will not keep up with increases in the prices of goods and services, than stocks. High Yield Bond--s that invest in lower-quality securities generally offer higher yields, but also carry more risk. Global/International Stocks--Foreign investments involve greater risks than U.S. investments, including political and economic risks and the risk of currency fluctuations, all of which may be magnified in emerging markets. Mid Cap--Investments in mid-sized companies may involve greater risks than those in larger, more well known companies, but may be less volatile than investments in smaller companies. Sector/Specialty--s with a narrow focus tend to be more volatile than funds that diversify across many sectors and companies. Small Cap--Investments in smaller companies may involve greater risks than those in larger, better known companies. Balanced/--Stock values fluctuate in response to the activities of individual companies and general market and economic conditions. Value--Investments in stocks can perform differently from the market as a whole. They can remain undervalued by the market for long periods of time. data was obtained from a third party mutual fund analytical firm. Although the data is gathered from a third party source believed to be reliable, MassMutual and its affiliates cannot guarantee the accuracy and/or completeness of the information. Money market funds are not insured or guaranteed by The Federal Deposit Insurance Corporation (FDIC) or any other government agency. Although the funds seek to preserve the value of the investment at $1.00 per share, it is possible to lose money by investing in the funds. Investors should consider an investment's objectives, risks, charges and expenses carefully before investing. For this and other information, see the prospectus available from MassMutual. Read them carefully. 2017 Massachusetts Mutual Life Insurance Company (MassMutual), Springfield, MA 01111-0001. All rights reserved. www.massmutual.com. CULLEN/FROST 401(K) PLAN 10