LETTER FROM ROBERT JULY 31, 2024 Dear Investor, Cimpress delivered strong financial results in our fourth quarter, topping off a strong FY2024 in which we posted our highest-ever fiscal year results for revenue, adjusted EBITDA and adjusted free cash flow. Throughout FY2024 we drove customer value improvements, steady revenue growth, gross margin expansion, and operating expense efficiencies, leading to significant profit expansion. From a balance sheet perspective, we continued to reduce net leverage and increase our liquidity while executing significant share repurchases at attractive prices. Summary results for Q4 FY2024 compared to Q4 FY2023: • Revenue grew 6% on a reported basis and on an organic constant-currency basis. • Consolidated operating income increased $12.4 million year over year to $66.3 million. • Adjusted EBITDA increased $5.4 million year over year to $119.4 million. Year-over-year currency movements negatively impacted adjusted EBITDA by $3.1 million for the quarter. • Operating cash flow increased $63.3 million year over year to $125.1 million. • Adjusted free cash flow increased $82.1 million year over year to $116.8 million. This includes the $16.8 million sale of our building in Jamaica as mentioned in our Q3 earnings document and strong inflows from working capital. • We repurchased 0.6 million Cimpress shares in Q4 FY2024 for $56.3 million at an average price per share of $88.20, inclusive of transaction costs. • Net leverage at June 30, 2024 was just under 3.0 times trailing-twelve month EBITDA as defined by our credit agreement, down from 3.9 last year. • Our liquidity position is strong with cash and marketable securities of $208.3 million as of June 30, 2024 compared to $173.4 million last year. Our $250 million revolving credit facility remained undrawn at the end of the quarter. • In May 2024 we repriced our senior secured term loan B, which will reduce our annualized cash interest expense by approximately $6 million over the four years remaining on this credit facility. Summary results for full-year FY2024 compared to FY2023: • Revenue grew 7% on a reported basis and 5% on an organic constant-currency basis. • Consolidated operating income increased $190.0 million year over year to $247.4 million. • Adjusted EBITDA increased $128.9 million year over year to $468.7 million. Year-over-year currency movements negatively impacted adjusted EBITDA by $18.8 million for the year. • Operating cash flow increased $220.4 million year over year to $350.7 million. • Adjusted free cash flow increased $237.7 million year over year to $261.1 million. • During FY2024, we repurchased 1.7 million Cimpress shares for $157.0 million at an average price per share of $91.09 inclusive of transaction costs. This represents a 7% reduction of the shares outstanding at June 30, 2023. • During FY2024, we purchased $26.2 million notional amount of our 7.0% Senior Notes Due 2026 for an aggregate purchase price, including transaction costs, of $24.5 million. Please see non-GAAP reconciliations at the end of this document. Page 2 of 31

Segment Commentary Vista grew Q4 revenue 8% on both a reported and organic constant-currency basis. Revenue increased across all of Vista's geographic markets, driven by customer experience improvements and new product introductions that have continued the multi-year trend of increases in average order value and supported growth in customer count for the sixth quarter in a row. Vista expanded segment EBITDA in Q4 FY2024 by $1.3 million to $79.1 million, a 2% increase from the same period last year. Segment EBITDA expansion was driven by revenue growth and gross profit growth helped by lower input costs. This was partially offset by higher advertising as a percentage of revenue that increased year over year by 130 basis points to 16.0%. Segment EBITDA in the year-ago period also benefited from over $3 million of one- time items that did not recur in the current year and impact the year-over-year comparison. For the full year, Vista revenue grew 8% on a reported basis and 7% on an organic constant-currency basis. Full- year segment EBITDA grew by $104.4 million to $328.5 million representing an expansion of segment EBITDA margin from 14% to 19%. PrintBrothers and The Print Group (our combined Upload & Print businesses) Q4 revenue grew year over year by 8% and 2%, respectively (6% combined), and 9% and 3%, respectively, on an organic constant-currency basis (7% combined). Order volumes continued to grow in these businesses, partially offset by lower per-order quantities in some product categories and weaker demand from reseller customers than from direct end-customer purchases. Combined Upload & Print EBITDA expanded $4.2 million, or 10% year over year in Q4 FY2024, driven by revenue growth, improved gross margins helped by lower input costs, and operating expense efficiencies. For the full year, PrintBrothers and The Print Group revenue grew by 10% and 3%, respectively (8% combined), and 7% and 0%, respectively, on an organic constant-currency basis (4% combined). Full-year combined Upload & Print EBITDA grew by $29.5 million to $160.4 million representing an expansion of combined EBITDA margin from 14% to 16%. National Pen revenue grew 2% on both a reported basis and an organic constant-currency basis during Q4 FY2024 driven by continued strength in e-commerce and fulfillment for other Cimpress businesses, partially offset by lower revenue from mail order sales that was impacted by reduced advertising spend to improve returns and efficiency. Segment EBITDA improved $6.0 million as a result of revenue growth, higher gross margins, a reduction in advertising as a percentage of revenue, and operating efficiencies. For the full year, National Pen revenue grew 7% on a reported basis and 5% on an organic constant-currency basis. Full-year segment EBITDA grew by $8.2 million to $31.9 million representing an expansion of segment EBITDA margin from 6% to 8%. All Other Businesses Q4 revenue grew 4% year over year on a reported basis and 5% on an organic constant- currency basis. Segment EBITDA declined with lower gross margins and the non-recurrence of a prior-year benefit in operating expenses related to variable long-term incentive compensation in BuildASign. For the full year, All Other Businesses revenue grew 1% on both a reported and organic constant-currency basis. Full-year segment EBITDA was flat at $25.2 million and segment EBITDA margin was flat at 12%. Central and Corporate Costs excluding unallocated share-based compensation increased $2.8 million year over year in Q4 FY2024 with higher volume-related operating costs. For the full year, central and corporate costs excluding unallocated share-based compensation decreased by $7.6 million to $133.8 million. Please see non-GAAP reconciliations at the end of this document. Page 3 of 31

Outlook, Leverage Policy and Capital Allocation Similar to what we conveyed last quarter, we believe that Cimpress will continue to benefit from print market dynamics that favor our mass customization business model, deliver continuous customer experience improvements, grow our scale-based advantages, and further improve our competitive position. Financially speaking, for the next several years we expect: • Consolidated constant-currency organic revenue to grow annually at mid-single-digit rates, possibly a little higher. • Adjusted EBITDA to grow slightly faster than revenue. • The multi-year conversion rate of adjusted EBITDA to adjusted free cash flow to be approximately 45% to 50%, with fluctuations from year to year. We target net leverage at or below approximately 2.5x trailing-twelve-month EBITDA as defined by our credit agreement. We may, from time-to-time, increase leverage to as high as approximately 3.0x for investments that we believe to have good returns and with a clear path to delever to the target of approximately 2.5x or below. We believe we could reach this 2.5x net leverage target in FY2025. However, if we continue to have attractive opportunities for share repurchases next fiscal year, we expect to exit FY2025 with net leverage at or below approximately 2.75x. From a capital allocation perspective, subject to the commentary in the prior two paragraphs, for FY2025 we expect to: • Make roughly similar levels of operating expense organic growth investment as we did in FY2024. • Increase capital expenditures to capitalize on opportunities we see for new products and productivity- enhancing production equipment. • Not deploy significant capital to M&A. • Repurchase shares and/or debt if available at an attractive price. Finally, investors should find the following information useful when estimating our FY2025 performance. We expect: • The year-over-year impact of currency movements on adjusted EBITDA to be approximately neutral relative to FY2024. • Cash interest expense to be about $12 million lower in FY2025 based on current interest rates. • Cash taxes to benefit from an approximately $10 million income tax refund previously expected by the end of FY2024. • Changes in net working capital to be a source of cash, but less favorable than it was in FY2024. Conclusion Q4 was a strong finish to a strong FY2024 in which we continued to improve both customer value and financial results. We remain focused on execution and our team is motivated and incentivized to build off of the strong financial progress we have demonstrated. For a discussion of FY2024 in terms of our strategy, scale-based advantages, capital allocation, our steady state free cash flow and the proxy we use to measure changes to our intrinsic value per share, please see my FY2024 annual letter to investors we also published today on ir.cimpress.com As always, I am grateful to the thousands of Cimpress team members who work every day to deliver value for our customers and appreciative of long-term shareholders and lenders who entrust us with your capital. Sincerely, Robert S. Keane Founder, Chairman & CEO Cimpress will host a public earnings call tomorrow, August 1, 2024 at 8:00 am ET, which you can join via the link on the events section of ir.cimpress.com. You may presubmit questions by emailing ir@cimpress.com, and you may also ask questions via chat during the live call. Also, please save the date for Cimpress' annual Investor Day event to be held via video conference on September 10, 2024 at 8:00 am ET. Please see non-GAAP reconciliations at the end of this document. Page 4 of 31

SUMMARY CONSOLIDATED RESULTS: THREE-YEAR TREND $ in thousands, except percentages REVENUE BY REPORTABLE SEGMENT, TOTAL REVENUE AND INCOME FROM OPERATIONS: Q4 FY2022 Q4 FY2023 Q4 FY2024 FY2022 FY2023 FY2024 Vista $ 368,099 $ 410,140 $ 441,906 $ 1,514,909 $ 1,613,887 $ 1,741,600 PrintBrothers 143,941 157,565 170,363 526,952 578,431 638,036 The Print Group 91,279 95,286 97,062 329,590 346,949 358,918 National Pen 75,608 82,894 84,184 341,832 366,294 391,192 All Other Businesses 51,786 52,593 54,621 205,862 213,455 215,807 Inter-segment eliminations (7,885) (9,632) (15,525) (31,590) (39,389) (53,697) Total revenue $ 722,828 $ 788,846 $ 832,611 $ 2,887,555 $ 3,079,627 $ 3,291,856 Reported revenue growth 14 % 9 % 6 % 12 % 7 % 7 % Organic constant currency revenue growth 19 % 9 % 6 % 13 % 11 % 5 % Income from operations $ (27,185) $ 53,895 $ 66,334 $ 47,298 $ 57,309 $ 247,351 Income from operations margin (4) % 7 % 8 % 2 % 2 % 8 % EBITDA BY REPORTABLE SEGMENT ("SEGMENT EBITDA") AND ADJUSTED EBITDA: Q4 FY2022 Q4 FY2023 Q4 FY2024 FY2022 FY2023 FY2024 Vista $ 12,101 $ 77,795 $ 79,070 $ 195,321 $ 224,081 $ 328,472 PrintBrothers 19,494 20,480 24,900 66,774 70,866 89,876 The Print Group 15,994 20,599 20,331 58,664 60,089 70,571 National Pen 4,192 3,564 9,540 26,845 23,714 31,917 All Other Businesses 6,028 8,595 6,788 23,227 25,215 25,195 Total segment EBITDA $ 57,809 $ 131,033 $ 140,629 $ 370,831 $ 403,965 $ 546,031 Central & corporate costs ex unallocated SBC (37,027) (31,919) (34,684) (137,116) (141,407) (133,845) Unallocated share-based compensation (1,991) 1,207 (3,436) (6,842) 7,868 (11,494) Exclude: share-based compensation expense1 13,551 10,418 17,085 49,766 39,682 65,584 Include: Realized gains (losses) on certain currency derivatives not included in segment EBITDA 5,411 3,171 (240) 4,424 29,724 2,406 Adjusted EBITDA $ 37,753 $ 113,910 $ 119,354 $ 281,063 $ 339,832 $ 468,682 Adjusted EBITDA margin 5 % 14 % 14 % 10 % 11 % 14 % Adjusted EBITDA year-over-year (decline) growth (39) % 202 % 5 % (19) % 21 % 38 % 1 SBC expense listed above excludes the portion included in restructuring-related charges to avoid double counting. Please see non-GAAP reconciliations at the end of this document. Page 5 of 31

SUMMARY CONSOLIDATED RESULTS: THREE-YEAR TREND (CONTINUED) $ in thousands, except where noted CASH FLOW AND OTHER METRICS: Q4 FY2022 Q4 FY2023 Q4 FY2024 FY2022 FY2023 FY2024 Net cash provided by (used in) operating activities $ 87,820 $ 61,815 $ 125,095 $ 219,536 $ 130,289 $ 350,722 Net cash provided by (used in) investing activities 44,630 4,626 (9,905) (3,997) (103,725) (54,614) Net cash provided by (used in) financing activities (7,826) (51,340) (65,046) (106,572) (177,106) (222,552) Adjusted free cash flow1,2 70,805 34,718 116,811 114,744 23,389 261,053 Cash interest, net2 33,561 39,713 38,755 94,869 102,501 118,103 COMPONENTS OF ADJUSTED FREE CASH FLOW: Q4 FY2022 Q4 FY2023 Q4 FY2024 FY2022 FY2023 FY2024 Adjusted EBITDA $ 37,753 $ 113,910 $ 119,354 $ 281,063 $ 339,832 $ 468,682 Cash restructuring payments (21) (22,288) (188) (265) (37,147) (7,585) Cash taxes (9,400) (7,690) (10,107) (32,987) (31,184) (49,414) Other changes in net working capital and other reconciling items 93,049 17,596 54,791 66,594 (38,711) 57,142 Purchases of property, plant and equipment (11,898) (16,286) (10,502) (54,040) (53,772) (54,927) Capitalization of software and website development costs (15,422) (13,606) (14,928) (65,297) (57,787) (58,307) Proceeds from sale of assets1 10,305 2,795 17,146 14,545 4,659 23,565 Adjusted free cash flow before cash interest, net $ 104,366 $ 74,431 $ 155,566 $ 209,613 $ 125,890 $ 379,156 Cash interest, net2 (33,561) (39,713) (38,755) (94,869) (102,501) (118,103) Adjusted free cash flow1,2 $ 70,805 $ 34,718 $ 116,811 $ 114,744 $ 23,389 $ 261,053 1 During the three months ended September 30, 2023, we revised our adjusted free cash flow metric to include proceeds from the sale of assets, which we believe provides useful information regarding the return on tangible or intangible assets that were used in operations. We have revised our presentation of all prior periods presented to reflect our revised adjusted free cash flow metric. 2 Cash interest, net is cash interest payments, partially offset by cash interest received on our cash and marketable securities. Prior to the third quarter of FY2023, we showed only the cash interest payments related to our borrowing activity in this chart in our earnings materials. We have recast all periods in the chart above to include the interest received. Please see non-GAAP reconciliations at the end of this document. Page 6 of 31

INCOME STATEMENT HIGHLIGHTS Revenue & Reported Revenue Growth (Decline) $723 $703 $845 $742 $789 $757 $921 $781 $833 14% 7% (1)% 13% 9% 8% 9% 5% 6% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Gross Profit ($M) & Gross Margin (%) $340 $326 $390 $347 $376 $359 $458 $376 $404 47% 46% 46% 47% 48% 47% 50% 48% 49% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 GAAP Operating Income (Loss) ($M) & Margin (%) (Quarterly) ($27) ($18) $34 ($12) $54 $34 $108 $39 $66 (4)% (3)% 4% (2)% 7% 5% 12% 5% 8% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Adjusted EBITDA ($M) & Margin (%) (Quarterly) $38 $46 $111 $69 $114 $89 $166 $94 $119 5% 7% 13% 9% 14% 12% 18% 12% 14% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Organic Constant-Currency Revenue Growth 19% 14% 5% 16% 9% 4% 6% 4% 6% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Contribution Profit ($M) & Contribution Margin (%) $215 $204 $259 $236 $267 $236 $319 $260 $286 30% 29% 31% 32% 34% 31% 35% 33% 34% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 GAAP Operating Income (Loss) ($M) & Margin (%) (TTM) $47 $12 ($40) ($24) $57 $109 $183 $235 $247 2% —% (1)% (1)% 2% 3% 6% 7% 8% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Adjusted EBITDA ($M) & Margin (%) (TTM) $281 $259 $228 $264 $340 $383 $438 $463 $469 10% 9% 8% 9% 11% 12% 14% 14% 14% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Please see non-GAAP reconciliations at the end of this document. Page 7 of 31

CASH FLOW Cash Flow from Operations ($M) (Quarterly) $88 $(25) $81 $13 $62 $42 $175 $8 $125 Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Adjusted Free Cash Flow & Cash Interest, Net ($M) (Quarterly) $71 ($52) $54 ($13) $35 $11 $150 ($17) $117 $34 $13 $33 $17 $40 $21 $40 $19 $39 FCF Cash interest, net Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Capital Expenditures & Capitalization of Software & Website Development Costs ($M) (Quarterly) (1) $12 $12 $15 $11 $16 $23 $11 $10 $11 $15 $15 $14 $15 $14 $14 $14 $15 $15 $27 $27 $29 $26 $30 $37 $25 $25 $25 Capital expenditures Capitalized software Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 (1) Values may not sum to total due to rounding. Cash Flow from Operations ($M) (TTM) $220 $158 $96 $156 $130 $198 $292 $287 $351 Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Adjusted Free Cash Flow & Cash Interest, Net ($M) (TTM) $115 $49 $(8) $59 $23 $87 $183 $179 $261 $95 $94 $92 $96 $103 $110 $117 $119 $118 FCF Cash interest, net Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Capital Expenditures & Capitalization of Software & Website Development Costs ($M) (TTM) $54 $57 $54 $49 $54 $65 $61 $61 $55 $65 $65 $62 $60 $58 $57 $57 $57 $58 $119 $122 $116 $109 $112 $122 $118 $118 $113 Capital expenditures Capitalized software Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Please see non-GAAP reconciliations at the end of this document. Page 8 of 31

CAPITAL STRUCTURE Net Debt (1) ($M) Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Cash / equivalents $ 277 $ 132 $ 111 $ 115 $ 130 $ 125 $ 274 $ 154 $ 204 Marketable securities $ 50 $ 124 $ 102 $ 75 $ 43 $ 23 $ 17 $ 6 $ 5 HY notes $ (600) $ (600) $ (600) $ (600) $ (548) $ (527) $ (522) $ (522) $ (522) Term loans $ (1,097) $ (1,076) $ (1,100) $ (1,103) $ (1,099) $ (1,087) $ (1,098) $ (1,088) $ (1,085) Revolver $ — $ — $ — $ — $ — $ — $ — $ — $ — Other debt $ (8) $ (7) $ (7) $ (8) $ (7) $ (6) $ (6) $ (5) $ (10) Net debt $ (1,378) $ (1,427) $ (1,494) $ (1,520) $ (1,481) $ (1,473) $ (1,335) $ (1,454) $ (1,408) (1) Excludes debt issuance costs, debt premiums and discounts. Values may not sum to total due to rounding. Weighted Average Shares Outstanding (Millions) (2) 26.1 26.2 26.2 26.3 26.3 26.5 26.6 26.2 25.3 26.1 26.2 26.2 26.3 26.6 27.1 27.2 26.2 26.6 Basic Diluted Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 (2) Basic and diluted shares are the same in certain periods where we reported a GAAP net loss. Consolidated Net Leverage Ratios (3) 4.23 4.82 5.52 4.83 3.90 3.51 2.87 3.01 2.97 2.42 2.82 3.34 2.97 2.49 2.29 1.78 1.95 1.90 Consolidated net leverage Senior secured net leverage Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 (3) Consolidated Net Leverage Ratios as calculated per our credit agreement definitions. Please see non-GAAP reconciliations at the end of this document. Page 9 of 31

SEGMENT RESULTS VISTA (QUARTERLY) Revenue ($M) & Reported Revenue Growth Quarterly $368 $369 $438 $397 $410 $397 $485 $418 $442 6% 6% (2)% 14% 11% 7% 11% 5% 8% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Gross Profit ($M) & Gross Margin (%) Quarterly $208 $199 $229 $219 $230 $219 $274 $230 $247 56% 54% 52% 55% 56% 55% 56% 55% 56% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Segment EBITDA ($M) & Segment EBITDA Margin (%) Quarterly $12 $31 $55 $60 $78 $74 $103 $72 $79 3% 8% 13% 15% 19% 19% 21% 17% 18% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Organic Constant-Currency Revenue Growth Quarterly 8% 8% 2% 16% 12% 6% 9% 5% 8% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Advertising ($M) & as % of Revenue Quarterly (1) $81 $68 $77 $57 $60 $58 $80 $63 $71 $64 $49 $57 $47 $42 $46 $55 $48 $51 $17 $19 $20 $10 $18 $11 $25 $15 $19 22% 18% 18% 15% 15% 15% 17% 15% 16% Lower-funnel ($M) Mid- & upper-funnel ($M) Total as % of revenue Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 (1) Values may not sum to total due to rounding. In Q4FY24, we reclassified $6.2 million of Q2FY24 ad spend from the lower-funnel category to the mid- & upper-funnel category with no change to total advertising spend. Please see non-GAAP reconciliations at the end of this document. Page 10 of 31

VISTA (ANNUAL) Revenue ($M) & Reported Revenue Growth Annual $1,499 $1,508 $1,337 $1,428 $1,515 $1,614 $1,742 11% 1% (11)% 7% 6% 7% 8% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Gross Profit ($M) & Gross Margin (%) Annual $898 $879 $802 $834 $865 $876 $970 60% 58% 60% 58% 57% 54% 56% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Segment EBITDA ($M) & Segment EBITDA Margin (%) Annual $310 $350 $363 $319 $195 $224 $328 21% 23% 27% 22% 13% 14% 19% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Organic Constant-Currency Revenue Growth Annual 9% 3% (10)% 1% 5% 9% 7% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Advertising ($M) & as % of Revenue Annual (1) $322 $282 $177 $206 $264 $262 $271$322 $282 $177 $180 $229 $195 $200 $26 $34 $67 $71 22% 19% 13% 14% 17% 16% 16% Lower-funnel ($M) [Total pre-2021] Mid- & upper-funnel ($M) Total as % of revenue FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 (1) Values may not sum to total due to rounding. Please see non-GAAP reconciliations at the end of this document. Page 11 of 31

UPLOAD AND PRINT PRINTBROTHERS (QUARTERLY): Revenue ($M) & Reported Revenue Growth Quarterly $144 $133 $149 $140 $158 $152 $165 $150 $170 36% 6% 8% 16% 9% 15% 11% 8% 8% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Organic Constant-Currency Revenue Growth Quarterly 52% 22% 18% 22% 7% 6% 5% 6% 9% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Gross Profit ($M) & Gross Margin (%) Quarterly $38 $34 $40 $36 $42 $41 $51 $43 $51 26% 25% 27% 26% 27% 27% 31% 28% 30% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Segment EBITDA ($M) & Segment EBITDA Margin (%) Quarterly $19 $15 $20 $16 $20 $20 $28 $17 $25 14% 11% 13% 11% 13% 13% 17% 11% 15% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 THE PRINT GROUP (QUARTERLY): Revenue ($M) & Reported Revenue Growth Quarterly $91 $77 $89 $86 $95 $81 $93 $88 $97 25% 6% 13% 4% 5% 4% 3% 2% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 0 100 Organic Constant-Currency Revenue Growth Quarterly 42% 24% 11% 19% 2% (3)% (1)% 2% 3% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Gross Profit ($M) & Gross Margin (%) Quarterly $32 $25 $30 $31 $38 $30 $34 $34 $38 35% 32% 33% 36% 40% 37% 37% 38% 39% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Segment EBITDA ($M) & Segment EBITDA Margin (%) Quarterly $16 $12 $14 $14 $21 $14 $18 $18 $20 18% 16% 15% 16% 22% 17% 20% 21% 21% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Please see non-GAAP reconciliations at the end of this document. Page 12 of 31

PRINTBROTHERS (ANNUAL): Revenue ($M) & Revenue Growth Annual $411 $444 $418 $422 $527 $578 $638 29% 8% (6)% 1% 25% 10% 10% 18% 13% (5)% (7)% 32% 17% 7% Reported Revenue ($M) Reported Revenue Growth Organic Constant Currency Revenue Growth FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Gross Profit ($M) & Margin Annual $99 $108 $101 $104 $138 $152 $186 24% 24% 24% 25% 26% 26% 29% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Segment EBITDA ($M) & Segment EBITDA Margin Annual $41 $43 $39 $43 $67 $71 $90 10% 10% 9% 10% 13% 12% 14% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 THE PRINT GROUP (ANNUAL): Revenue ($M) & Revenue Growth Annual $320 $326 $275 $276 $330 $347 $359 19% 2% (16)% —% 20% 5% 3% 9% 6% (13)% (7)% 27% 13% —% Reported Revenue ($M) Reported Revenue Growth Organic Constant Currency Revenue Growth FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Gross Profit ($M) & Gross Margin Annual $112 $111 $90 $93 $116 $123 $136 35% 34% 33% 34% 35% 36% 38% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Segment EBITDA ($M) & Segment EBITDA Margin Annual $64 $64 $52 $43 $59 $60 $71 20% 20% 19% 16% 18% 17% 20% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Please see non-GAAP reconciliations at the end of this document. Page 13 of 31

NATIONAL PEN (QUARTERLY): Revenue ($M) & Reported Revenue Growth Quarterly $76 $82 $121 $81 $83 $87 $131 $89 $84 10% 18% (3%) 12% 10% 7% 8% 10% 2% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Gross Profit ($M) & Gross Margin (%) Quarterly $39 $44 $65 $41 $42 $45 $72 $48 $44 52% 54% 54% 51% 50% 52% 55% 54% 52% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Organic Constant-Currency Revenue Growth Quarterly 14% 24% 3% 15% 10% 5% 5% 10% 2% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Segment EBITDA (Loss) ($M) & Segment EBITDA (Loss) Margin (%) Quarterly $4 ($1) $25 ($3) $4 ($8) $26 $5 $10 6% (2%) 21% (4%) 4% (10%) 20% 5% 11% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Please see non-GAAP reconciliations at the end of this document. Page 14 of 31

NATIONAL PEN (ANNUAL) Revenue ($M) & Reported Revenue Growth Annual (1) $333 $348 $299 $314 $342 $366 $391 5% (14)% 5% 9% 7% 7% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Gross Profit ($M) & Gross Margin (%) Annual $193 $197 $159 $153 $182 $192 $209 58% 57% 53% 49% 53% 52% 53% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 (1) National Pen was acquired at the end of Q2 2017. The annual growth rates above are shown from 2019, as 2018 was the first full fiscal year of ownership. Organic Constant-Currency Revenue Growth Annual (1) 7% (13)% 2% 11% 12% 5% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Segment EBITDA ($M) & Segment EBITDA Margin (%) Annual $29 $17 $8 $12 $27 $24 $32 9% 5% 3% 4% 8% 6% 8% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Please see non-GAAP reconciliations at the end of this document. Page 15 of 31

ALL OTHER BUSINESSES (QUARTERLY): Revenue ($M) & Reported Revenue Growth Quarterly $52 $52 $60 $49 $53 $52 $60 $49 $55 5% 8% 4% 1% 2% —% —% —% 4% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Gross Profit ($M) & Gross Margin (%) Quarterly $25 $24 $27 $20 $24 $24 $27 $21 $25 48% 46% 45% 42% 46% 46% 45% 43% 45% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Organic Constant-Currency Revenue Growth Quarterly 3% 8% 3% 1% 2% (1%) —% —% 5% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Segment EBITDA ($M) & Segment EBITDA Margin (%) Quarterly $6 $6 $5 $5 $9 $6 $8 $4 $7 12% 12% 9% 10% 16% 12% 13% 8% 12% Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Please see non-GAAP reconciliations at the end of this document. Page 16 of 31

ALL OTHER BUSINESSES (ANNUAL): Revenue ($M) & Reported Revenue Growth Annual $40 $136 $174 $192 $206 $213 $216 (57%) 239% 28% 11% 7% 4% 1% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Gross Profit ($M) & Gross Margin (%) Annual $12 $55 $80 $96 $96 $96 $97 30% 40% 46% 50% 46% 45% 45% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Organic Constant-Currency Revenue Growth Annual 54% 7% 4% 12% 3% 4% 1% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Segment EBITDA (Loss) ($M) & Segment EBITDA (Loss) Margin (%) Annual ($11) ($6) $17 $32 $23 $25 $25 (26%) (5%) 10% 17% 11% 12% 12% FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Please see non-GAAP reconciliations at the end of this document. Page 17 of 31

CENTRAL AND CORPORATE COSTS Central and Corporate Costs ($M) Quarterly (1) $13 $13 $13 $16 $12 $12 $12 $12 $12 $18 $17 $17 $17 $17 $17 $17 $19 $19 $7 $6 $6 $6 $3 $3 $3 $3 $3 $2 $(1) $(2) $(4) $(1) $— $4 $5 $3 $39 $35 $34 $34 $31 $32 $36 $39 $38 Corporate Costs Central Operating Costs MCP Investment Unallocated SBC Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Central and Corporate Costs ($M) TTM (1) $47 $48 $50 $54 $53 $52 $52 $48 $49 $66 $67 $68 $68 $68 $68 $68 $71 $73 $24 $25 $25 $24 $21 $18 $15 $12 $12 $7 $5 $1 $(5) $(8) ($7) ($2) $7 $11 $144 $144 $144 $142 $134 $131 $133 $138 $145 Corporate Costs Central Operating Costs MCP Investment Unallocated SBC Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 (1) Values may not sum to total due to rounding. Please see non-GAAP reconciliations at the end of this document. Page 18 of 31

CURRENCY IMPACTS Changes in currency rates negatively impacted our year- over-year reported revenue growth in Q4 FY2024 by less than 100 basis points. There are many natural expense offsets in local currencies in our business, so the net currency impact to our bottom line is less pronounced than it is to revenue. We enter into currency derivative contracts to hedge the risk for certain currencies where we have a net adjusted EBITDA exposure. We do not apply hedge accounting to these hedges, which increases the volatility of the gains or losses that are included in our net income from quarter to quarter. Realized and unrealized gains or losses from these hedges are recorded in Other income (expense), net, along with other currency-related gains or losses. The realized gains or losses on certain hedging contracts are added to our adjusted EBITDA to show the economic impact of our hedging activities. Our Other income (expense), net was ($0.8) million in Q4 FY2024, mainly driven by: • Realized losses on certain currency hedges intended to hedge EBITDA were $0.2 million in Q4. These realized losses affect our net income, adjusted EBITDA, and adjusted free cash flow. They are not allocated to segment-level EBITDA. • Other net losses were $0.6 million in Q4, a mix of realized losses and net unrealized gains on the revaluation of currency derivatives, and intercompany, cash and debt balances. These are included in our net income but excluded from our adjusted EBITDA. On the right side of this page is a table describing the directional net currency impacts when compared to the prior-year period, as well as a table describing impacts to segment EBITDA. Y/Y Impact from Currency* Financial Measure Q4 FY2024 FY2024 Revenue Negative Positive Operating income Positive Positive Net income Negative Negative Adjusted EBITDA Negative Negative Adjusted free cash flow Negative Negative *Net income includes both realized and unrealized gains or losses from currency hedges and intercompany loan balances. Adjusted EBITDA includes only realized gains or losses from certain currency hedges. Adjusted free cash flow includes realized gains or losses on currency hedges as well as the currency impact of the timing of receivables, payments and other working capital settlements. Revenue, operating income and segment EBITDA do not reflect any impacts from currency hedges or balance sheet translation. Y/Y Impact from Currency* Segment EBITDA Q4 FY2024 FY2024 Vista Neutral $4.7M Upload & Print ($0.5)M $5.2M National Pen Neutral ($1.2)M All Other Businesses Neutral Neutral *Realized gains or losses on currency hedges that we include in adjusted EBITDA are not allocated to segment-level EBITDA. Other Income (Expense), Net ($M) $23 $27 ($17) $1 $7 $6 $— ($4) ($1) Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Realized Gains (Losses) on Certain Currency Derivatives Intended to Hedge EBITDA ($M) $5 $7 $15 $5 $3 $2 $1 $— $— Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Please see non-GAAP reconciliations at the end of this document. Page 19 of 31

CIMPRESS PLC CONSOLIDATED BALANCE SHEETS (unaudited in thousands, except share and per share data) June 30, 2024 June 30, 2023 Assets Current assets: Cash and cash equivalents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 203,775 $ 130,313 Marketable securities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4,500 38,540 Accounts receivable, net of allowances of $7,219 and $6,630, respectively . . . . . . . . . . . . . . . . . 64,576 67,353 Inventory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97,016 107,835 Prepaid expenses and other current assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88,112 96,986 Total current assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 457,979 441,027 Property, plant and equipment, net . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 265,177 287,574 Operating lease assets, net . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78,681 76,776 Software and website development costs, net . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92,212 95,315 Deferred tax assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95,059 12,740 Goodwill . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 787,138 781,541 Intangible assets, net . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76,560 109,196 Marketable securities, non-current . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — 4,497 Other assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39,351 46,193 Total assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 1,892,157 $ 1,854,859 Liabilities, noncontrolling interests and shareholders’ deficit Current liabilities: Accounts payable . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 326,656 $ 285,784 Accrued expenses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 245,931 257,109 Deferred revenue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46,118 44,698 Short-term debt . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12,488 10,713 Operating lease liabilities, current . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19,634 22,559 Other current liabilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13,136 24,469 Total current liabilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 663,963 645,332 Deferred tax liabilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24,701 47,351 Long-term debt . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1,591,807 1,627,243 Operating lease liabilities, non-current . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61,895 56,668 Other liabilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76,305 90,058 Total liabilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2,418,671 2,466,652 Redeemable noncontrolling interests . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22,998 10,893 Shareholders’ deficit: Preferred shares, nominal value €0.01 per share, 100,000,000 shares authorized; none issued and outstanding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — — Ordinary shares, nominal value €0.01 per share, 100,000,000 shares authorized; 43,051,269 and 44,315,855 shares issued; 25,080,022 and 26,344,608 shares outstanding, respectively . . 604 615 Treasury shares, at cost, 17,971,247 for both periods presented . . . . . . . . . . . . . . . . . . . . . . . . . . . (1,363,550) (1,363,550) Additional paid-in capital . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 570,283 539,454 Retained earnings . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 272,881 235,396 Accumulated other comprehensive loss . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (30,364) (35,060) Total shareholders’ deficit attributable to Cimpress plc . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (550,146) (623,145) Noncontrolling interests . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 634 459 Total shareholders' deficit . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (549,512) (622,686) Total liabilities, noncontrolling interests and shareholders’ deficit . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 1,892,157 $ 1,854,859 Page 20 of 31

CIMPRESS PLC CONSOLIDATED STATEMENTS OF OPERATIONS (unaudited in thousands, except share and per share data) Three Months Ended June 30, Year Ended June 30, 2024 2023 2024 2023 Revenue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 832,611 $ 788,846 $ 3,291,856 $ 3,079,627 Cost of revenue (1) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 428,188 412,589 1,695,062 1,640,625 Technology and development expense (1) . . . . . . . . . . . . . . . . . . . . . . . 83,887 71,772 321,968 302,257 Marketing and selling expense (1, 2) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 194,250 180,658 789,872 773,970 General and administrative expense (1) . . . . . . . . . . . . . . . . . . . . . . . . . 54,349 52,805 205,737 209,246 Amortization of acquired intangible assets . . . . . . . . . . . . . . . . . . . . . . . 5,457 10,903 31,443 46,854 Restructuring expense (1) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 146 615 423 43,757 Impairment of goodwill . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — 5,609 — 5,609 Income from operations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66,334 53,895 247,351 57,309 Other (expense) income, net . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (794) 7,116 1,583 18,498 Interest expense, net . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (29,876) (28,875) (119,822) (112,793) (Loss) Gain on early extinguishment of debt . . . . . . . . . . . . . . . . . . . . . . (2,387) 6,764 (666) 6,764 Income (loss) before income taxes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33,277 38,900 128,446 (30,222) Income tax (benefit) expense (3) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (84,889) 11,524 (49,362) 155,493 Net income (loss) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 118,166 27,376 177,808 (185,715) Add: Net (income) loss attributable to noncontrolling interest . . . . . . . (3,165) 1,413 (4,126) (263) Net income (loss) attributable to Cimpress plc . . . . . . . . . . . . . . . . . . . . $ 115,001 $ 28,789 $ 173,682 $ (185,978) Basic net income (loss) per share attributable to Cimpress plc . . . . . . $ 4.55 $ 1.09 $ 6.64 $ (7.08) Diluted net income (loss) per share attributable to Cimpress plc . . . . $ 4.33 $ 1.08 $ 6.43 $ (7.08) Weighted average shares outstanding — basic . . . . . . . . . . . . . . . . . . . 25,292,515 26,330,801 26,151,968 26,252,860 Weighted average shares outstanding — diluted . . . . . . . . . . . . . . . . . . 26,569,804 26,617,054 27,004,687 26,252,860 ____________________________________________ (1) Share-based compensation is allocated as follows: Three Months Ended June 30, Year Ended June 30, 2024 2023 2024 2023 Cost of revenue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 179 $ 63 $ 820 $ 474 Technology and development expense . . . . . . . . . . . . . . . . . . . . . . . . . . 5,268 3,194 20,869 13,002 Marketing and selling expense . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3,055 1,805 11,680 5,693 General and administrative expense . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8,583 5,356 32,215 20,513 Restructuring expense . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — 299 — 2,440 (2) Marketing and selling expense components are as follows: Three Months Ended June 30, Year Ended June 30, 2024 2023 2024 2023 Advertising . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 103,947 $ 95,389 $ 436,494 $ 417,886 Payment processing . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14,583 14,196 59,794 55,424 All other marketing and selling expense . . . . . . . . . . . . . . . . . . . . . . . . . 75,720 71,073 293,584 300,660 (3) Income tax expense (benefit) for Q4 and full-year FY2024 results includes a $105.8 million benefit from the partial release of a valuation allowance against deferred tax assets in Switzerland. In Q2 FY2023 we recorded an increase to the Swiss valuation allowance of $116.7 million. The changes in the valuation allowance did not impact our cash taxes in any period. We expect to utilize the non-reserved deferred tax assets in future years. Page 21 of 31

CIMPRESS PLC CONSOLIDATED STATEMENTS OF CASH FLOWS (unaudited in thousands) Three Months Ended June 30, Year Ended June 30, 2024 2023 2024 2023 Operating activities Net income (loss) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 118,166 $ 27,376 $ 177,808 $ (185,715) Adjustments to reconcile net income (loss) to net cash provided by operating activities: Depreciation and amortization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35,661 40,861 151,764 162,428 Impairment of goodwill . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — 5,609 — 5,609 Share-based compensation expense . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17,085 10,717 65,584 42,122 Deferred taxes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (95,512) (1,072) (94,442) 114,912 Loss (gain) on early extinguishment of debt . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2,236 (6,764) 515 (6,764) Unrealized (loss) gain on derivatives not designated as hedging instruments included in net income (loss) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (440) 1,881 (4,992) 34,393 Effect of exchange rate changes on monetary assets and liabilities denominated in non-functional currency . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (262) (5,016) 116 (11,988) Other non-cash items . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1,072 (1,965) 1,615 13,235 Changes in operating assets and liabilities, net of effects of businesses acquired: . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Accounts receivable . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6,590 597 161 (4,243) Inventory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4,772 13,947 11,778 11,352 Prepaid expenses and other assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10,600 6,839 15,560 1,768 Accounts payable . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50,740 16,122 39,276 (28,872) Accrued expenses and other liabilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (25,613) (47,317) (14,021) (17,948) Net cash provided by operating activities 125,095 61,815 350,722 130,289 Investing activities Purchases of property, plant and equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (10,502) (16,286) (54,927) (53,772) Business acquisitions, net of cash acquired . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (3,621) — (3,621) (498) Capitalization of software and website development costs . . . . . . . . . . . . . . . . . . . (14,928) (13,606) (58,307) (57,787) Proceeds from the sale of assets . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17,146 2,795 23,565 4,659 Purchases of marketable securities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — — — (84,030) Proceeds from maturity of held-to-maturity investments . . . . . . . . . . . . . . . . . . . . . 2,000 32,000 38,676 92,110 Proceeds from the sale of subsidiaries, net of transaction costs and cash divested . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — — — (4,130) Other investing activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — (277) — (277) Net cash (used in) provided by investing activities (9,905) 4,626 (54,614) (103,725) Financing activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Proceeds from borrowings of debt . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 204,889 — 205,775 48,264 Payments of debt . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (207,939) (3,363) (219,722) (61,310) Payments for purchase of 7% Senior Notes due 2026 . . . . . . . . . . . . . . . . . . . . . . . — (44,994) (24,471) (44,994) Payments of debt issuance costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (2,076) — (2,076) (51) Payments of purchase consideration included in acquisition-date fair value . . . . — — — (7,100) Payments of withholding taxes in connection with equity awards . . . . . . . . . . . . . . (2,355) (639) (16,424) (4,448) Payments of finance lease obligations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (2,639) (2,273) (10,140) (8,290) Purchase of noncontrolling interests . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — — (65) (95,567) Purchase of ordinary shares . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (56,253) — (156,982) — Proceeds from issuance of ordinary shares . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1,327 327 2,102 327 Distributions to noncontrolling interests . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — — (549) (3,652) Other financing activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . — (398) — (285) Net cash used in financing activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (65,046) (51,340) (222,552) (177,106) Effect of exchange rate changes on cash . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (707) 222 (94) 3,802 Net increase (decrease) in cash and cash equivalents . . . . . . . . . . . . . . . . . . . . . . 49,437 15,323 73,462 (146,740) Cash and cash equivalents at beginning of period . . . . . . . . . . . . . . . . . . . . . . . . . . 154,338 114,990 130,313 277,053 Cash and cash equivalents at end of period . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . $ 203,775 $ 130,313 $ 203,775 $ 130,313 Page 22 of 31

ABOUT NON-GAAP FINANCIAL MEASURES: To supplement Cimpress’ consolidated financial statements presented in accordance with U.S. generally accepted accounting principles, or GAAP, Cimpress has used the following measures defined as non-GAAP financial measures by Securities and Exchange Commission, or SEC, rules: Constant-currency revenue growth, constant-currency revenue growth excluding revenue from acquisitions and divestitures made during the last twelve months, constant-currency gross profit growth, adjusted EBITDA, adjusted free cash flow and cash interest, net: • Constant-currency revenue growth is estimated by translating all non-U.S. dollar denominated revenue generated in the current period using the prior year period’s average exchange rate for each currency to the U.S. dollar. • Constant-currency revenue growth excluding revenue from acquisitions and divestitures made during the past twelve months excludes the impact of currency as defined above. The organic constant-currency growth rate excludes 99designs revenue from Q2 FY2021 through Q1 FY2022, Depositphotos/VistaCreate revenue from Q2 FY2022 through Q1 FY2023, and the revenue from several small acquired businesses for the first year after acquisition. • Constant-currency gross profit growth is estimated by translating all non-U.S. dollar denominated revenue and cost of revenue generated or incurred in the current period using the prior year period’s average exchange rate for each currency to the U.S. dollar. • Adjusted EBITDA is defined as GAAP operating income plus depreciation and amortization plus share-based compensation expense plus proceeds from insurance not already included in operating income plus earn-out related charges plus certain impairments plus restructuring related charges plus realized gains or losses on currency derivatives less the gain or loss on purchase or sale of subsidiaries as well as the disposal of assets. • Adjusted free cash flow is defined as net cash provided by operating activities less purchases of property, plant and equipment, purchases of intangible assets not related to acquisitions, and capitalization of software and website development costs, plus payment of contingent consideration in excess of acquisition-date fair value, gains on proceeds from insurance, and proceeds from the sale of assets. • Cash interest, net is cash paid for interest, less cash received for interest. These non-GAAP financial measures are provided to enhance investors' understanding of our current operating results from the underlying and ongoing business for the same reasons they are used by management. For example, for acquisitions we believe excluding the costs related to the purchase of a business (such as amortization of acquired intangible assets, contingent consideration, or impairment of goodwill) provides further insight into the performance of the underlying acquired business in addition to that provided by our GAAP operating income. As another example, as we do not apply hedge accounting for certain derivative contracts, we believe inclusion of realized gains and losses on these contracts that are intended to be matched against operational currency fluctuations provides further insight into our operating performance in addition to that provided by our GAAP operating income. We do not, nor do we suggest that investors should, consider such non-GAAP financial measures in isolation from, or as a substitute for, financial information prepared in accordance with GAAP. For more information on these non-GAAP financial measures, please see the tables captioned “Reconciliations of Non-GAAP Financial Measures” included at the end of this document. The tables have more details on the GAAP financial measures that are most directly comparable to non-GAAP financial measures and the related reconciliation between these financial measures. Page 23 of 31

CONSTANT-CURRENCY REVENUE GROWTH RATES (Quarterly) Total Company Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 14 % 7 % (1) % 13 % 9 % 8 % 9 % 5 % 6 % Currency impact 7 % 8 % 7 % 3 % — % (4) % (3) % (1) % — % Revenue growth in constant currency 21 % 15 % 6 % 16 % 9 % 4 % 6 % 4 % 6 % Impact of TTM acquisitions, divestitures & JVs (2) % (1) % (1) % — % — % — % — % — % — % Revenue growth in constant currency ex. TTM acquisitions, divestitures & JVs 19 % 14 % 5 % 16 % 9 % 4 % 6 % 4 % 6 % Vista Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 6 % 6 % (2) % 14 % 11 % 7 % 11 % 5 % 8 % Currency impact 4 % 4 % 4 % 2 % 1 % (1) % (2) % — % — % Revenue growth in constant currency 10 % 10 % 2 % 16 % 12 % 6 % 9 % 5 % 8 % Impact of TTM acquisitions, divestitures & JVs (2) % (2) % — % — % — % — % — % — % — % Revenue growth in constant currency ex. TTM acquisitions, divestitures & JVs 8 % 8 % 2 % 16 % 12 % 6 % 9 % 5 % 8 % PrintBrothers Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 36 % 6 % 8 % 16 % 9 % 15 % 11 % 8 % 8 % Currency impact 18 % 17 % 12 % 5 % (2) % (9) % (6) % (2) % 1 % Revenue growth in constant currency 54 % 23 % 20 % 21 % 7 % 6 % 5 % 6 % 9 % Impact of TTM acquisitions (2) % (1) % (2) % 1 % — % — % — % — % — % Revenue growth in constant currency excl. TTM acquisitions 52 % 22 % 18 % 22 % 7 % 6 % 5 % 6 % 9 % The Print Group Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 25 % 6 % (1) % 13 % 4 % 5 % 4 % 3 % 2 % Currency impact 17 % 18 % 12 % 6 % (2) % (8) % (5) % (1) % 1 % Revenue growth in constant currency 42 % 24 % 11 % 19 % 2 % (3) % (1) % 2 % 3 % National Pen Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 10 % 18 % (3) % 12 % 10 % 7 % 8 % 10 % 2 % Currency impact 4 % 6 % 6 % 3 % — % (2) % (3) % — % — % Revenue growth in constant currency 14 % 24 % 3 % 15 % 10 % 5 % 5 % 10 % 2 % All Other Businesses Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 5 % 8 % 4 % 1 % 2 % — % — % — % 4 % Currency impact (1) % — % (1) % — % — % (1) % — % — % 1 % Revenue growth in constant currency 4 % 8 % 3 % 1 % 2 % (1) % — % — % 5 % Impact of TTM acquisitions and divestitures (1) % — % — % — % — % — % — % — % — % Revenue growth in constant currency excl. TTM acquisitions & divestitures 3 % 8 % 3 % 1 % 2 % (1) % — % — % 5 % Note: Total company revenue growth in constant currency excluding TTM acquisitions, divestitures and joint ventures for all periods excludes the impact of currency. The organic constant-currency growth rate excludes 99designs revenue in Q1 FY2022, Depositphotos/VistaCreate revenue from Q2 FY2022 through Q1 FY2023, and the revenue from several small acquired businesses for the first year after acquisition. Values may not sum to total due to rounding. Page 24 of 31

CONSTANT-CURRENCY REVENUE GROWTH RATES (CONT.) (Quarterly) Upload and Print ($M) Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 PrintBrothers reported revenue $ 143.9 $ 132.7 $ 148.6 $ 139.6 $ 157.6 $ 152.2 $ 165.1 $ 150.3 $ 170.4 The Print Group reported revenue $ 91.3 $ 76.8 $ 89.3 $ 85.5 $ 95.3 $ 80.5 $ 93.3 $ 88.0 $ 97.1 Upload and Print inter-segment eliminations $ (0.2) $ (0.1) $ (0.2) $ (0.2) $ (0.2) $ (0.1) $ (0.2) $ (0.1) $ (0.2) Total Upload and Print revenue in USD $ 235.0 $ 209.4 $ 237.7 $ 224.9 $ 252.7 $ 232.6 $ 258.2 $ 238.2 $ 267.3 Upload and Print Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Reported revenue growth 32 % 6 % 4 % 15 % 7 % 11 % 9 % 6 % 6 % Currency impact 17 % 18 % 13 % 5 % (2) % (8) % (6) % (2) % 1 % Revenue growth in constant currency 49 % 24 % 17 % 20 % 5 % 3 % 3 % 4 % 7 % Impact of TTM acquisitions (2) % (1) % (2) % 1 % — % — % — % — % — % Revenue growth in constant currency excl. TTM acquisitions 47 % 23 % 15 % 21 % 5 % 3 % 3 % 4 % 7 % CONSTANT-CURRENCY REVENUE GROWTH RATES (Annual) Total Company FY2022 FY2023 FY2024 Reported revenue growth 12 % 7 % 7 % Currency impact 3 % 4 % (2) % Revenue growth in constant currency 15 % 11 % 5 % Impact of TTM acquisitions, divestitures & JVs (2) % — % — % Revenue growth in constant currency ex. TTM acquisitions, divestitures & JVs 13 % 11 % 5 % Vista FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Reported revenue growth 11 % 1 % (11) % 7 % 6 % 7 % 8 % Currency impact (2) % 2 % 1 % (3) % 1 % 2 % (1) % Revenue growth in constant currency 9 % 3 % (10) % 4 % 7 % 9 % 7 % Impact of TTM acquisitions, divestitures & JVs — % — % — % (3) % (2) % — % — % Revenue growth in constant currency ex. TTM acquisitions, divestitures & JVs 9 % 3 % (10) % 1 % 5 % 9 % 7 % PrintBrothers FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Reported revenue growth 29 % 8 % (6) % 1 % 25 % 10 % 10 % Currency impact (11) % 5 % 3 % (7) % 8 % 8 % (3) % Revenue growth in constant currency 18 % 13 % (3) % (6) % 33 % 18 % 7 % Impact of TTM acquisitions, divestitures & JVs — % — % (2) % (1) % (1) % (1) % — % Revenue growth in constant currency ex. TTM acquisitions, divestitures & JVs 18 % 13 % (5) % (7) % 32 % 17 % 7 % Values may not sum to total due to rounding. Page 25 of 31

CONSTANT-CURRENCY REVENUE GROWTH RATES (CONT.) (Annual) The Print Group FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Reported revenue growth 19 % 2 % (16) % — % 20 % 5 % 3 % Currency impact (10) % 4 % 3 % (7) % 7 % 8 % (3) % Revenue growth in constant currency 9 % 6 % (13) % (7) % 27 % 13 % — % National Pen (1) FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Reported revenue growth 5 % (14) % 5 % 9 % 7 % 7 % Currency impact 2 % 1 % (3) % 2 % 5 % (2) % Revenue growth in constant currency 7 % (13) % 2 % 11 % 12 % 5 % Upload and Print ($M) FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 PrintBrothers reported revenue $ 410.8 $ 444.0 $ 417.9 $ 421.8 $ 527.0 $ 578.4 $ 638.0 The Print Group reported revenue $ 320.5 $ 325.9 $ 275.2 $ 275.5 $ 329.6 $ 346.9 $ 358.9 Upload and Print inter-segment eliminations $ (1.3) $ (1.0) $ (1.0) $ (1.3) $ (0.9) $ (0.6) $ (0.6) Total Upload and Print revenue in USD $ 730.0 $ 768.9 $ 692.1 $ 696.0 $ 855.6 $ 924.7 $ 996.3 Upload and Print FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Reported revenue growth 24 % 5 % (10) % 1 % 23 % 8 % 8 % Currency impact 11 % 5 % 3 % (8) % 7 % 8 % (4) % Revenue growth in constant currency 13 % 10 % (7) % (7) % 30 % 16 % 4 % All Other Businesses FY2018 FY2019 FY2020 FY2021 FY2022 FY2023 FY2024 Reported revenue growth (57) % 239 % 28 % 11 % 7 % 4 % 1 % Currency impact — % 9 % 1 % 1 % — % — % — % Revenue growth in constant currency (57) % 248 % 29 % 12 % 7 % 4 % 1 % Impact of TTM acquisitions, divestitures & JVs 110 % (241) % (25) % — % (4) % — % — % Revenue growth in constant currency ex. TTM acquisitions, divestitures & JVs 54 % 7 % 4 % 12 % 3 % 4 % 1 % (1) National Pen was acquired at the end of Q2 2017. The annual growth rates above are shown from 2019, as 2018 was the first full fiscal year of ownership. Values may not sum to total due to rounding. Page 26 of 31

EBITDA (LOSS) BY REPORTABLE SEGMENT ("SEGMENT EBITDA") (Quarterly, in millions) Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Vista $ 12.1 $ 30.7 $ 55.2 $ 60.4 $ 77.8 $ 74.4 $ 103.2 $ 71.8 $ 79.1 PrintBrothers 19.5 15.0 19.5 15.9 20.5 19.8 28.3 16.8 24.9 The Print Group 16.0 12.2 13.7 13.6 20.6 13.6 18.4 18.2 20.3 National Pen 4.2 (1.3) 24.8 (3.3) 3.6 (8.3) 25.9 4.8 9.5 All Other Businesses 6.0 6.2 5.4 5.0 8.6 6.5 8.0 4.0 6.8 Total segment EBITDA $ 57.8 $ 62.8 $ 118.5 $ 91.6 $ 131.0 $ 106.0 $ 183.8 $ 115.6 $ 140.6 Central and corporate costs ex. unallocated SBC (37.0) (35.5) (35.6) (38.4) (31.9) (32.1) (32.1) (34.9) (34.7) Unallocated SBC (2.0) 1.0 1.8 3.9 1.2 0.3 (3.9) (4.5) (3.4) Exclude: share-based compensation included in segment EBITDA 13.6 10.5 11.5 7.2 10.4 12.5 17.6 18.4 17.1 Include: Realized gains (losses) on certain currency derivatives not included in segment EBITDA 5.4 6.9 14.9 4.8 3.2 2.1 0.9 (0.3) (0.2) Adjusted EBITDA2,3 $ 37.8 $ 45.6 $ 111.2 $ 69.1 $ 113.9 $ 88.7 $ 166.4 $ 94.2 $ 119.4 Depreciation and amortization (42.3) (40.9) (40.9) (39.8) (40.9) (39.9) (39.1) (37.1) (35.7) Share-based compensation expense1 (13.6) (10.5) (11.5) (7.2) (10.4) (12.5) (17.6) (18.4) (17.1) Certain impairments and other adjustments 6.5 (3.5) 0.9 0.5 (5.0) (0.5) (0.6) 0.3 (0.4) Restructuring-related charges (10.2) (1.8) (11.2) (30.1) (0.6) 0.3 (0.5) (0.1) (0.1) Realized (gains) losses on currency derivatives not included in operating income (5.4) (6.9) (14.9) (4.8) (3.2) (2.1) (0.9) 0.3 0.2 Total income (loss) from operations $ (27.2) $ (18.0) $ 33.6 $ (12.2) $ 53.9 $ 34.1 $ 107.7 $ 39.2 $ 66.3 Operating income (loss) margin (4) % (3) % 4 % (2) % 7 % 5 % 12 % 5 % 8 % Operating income (loss) year-over-year growth (401) % (206) % (61) % 57 % 298 % 290 % 221 % 422 % 23 % 1SBC expense listed here excludes the portion included in restructuring-related charges to avoid double counting. 2This metric uses the definition of adjusted EBITDA as outlined above and therefore does not include the pro-forma impact of acquisitions, divestitures or the annualized benefit from actioned cost saving initiatives; however, our debt covenants allow for the inclusion of pro-forma impacts to adjusted EBITDA. 3Adjusted EBITDA includes 100% of the results of our consolidated subsidiaries and therefore does not give effect to adjusted EBITDA attributable to noncontrolling interests. This is to most closely align to our debt covenant and cash flow reporting. Values may not sum to total due to rounding. Page 27 of 31

ADJUSTED EBITDA (Quarterly, in millions) Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 GAAP operating income (loss) $ (27.2) $ (18.0) $ 33.6 $ (12.2) $ 53.9 $ 34.1 $ 107.7 $ 39.2 $ 66.3 Depreciation and amortization $ 42.3 $ 40.9 $ 40.9 $ 39.8 $ 40.9 $ 39.9 $ 39.1 $ 37.1 $ 35.7 Share-based compensation expense1 $ 13.6 $ 10.5 $ 11.5 $ 7.2 $ 10.4 $ 12.5 $ 17.6 $ 18.4 $ 17.1 Certain impairments and other adjustments $ (6.5) $ 3.5 $ (0.9) $ (0.5) $ 5.0 $ 0.5 $ 0.6 $ (0.3) $ 0.4 Restructuring related charges $ 10.2 $ 1.8 $ 11.2 $ 30.1 $ 0.6 $ (0.3) $ 0.5 $ 0.1 $ 0.1 Realized gains (losses) on currency derivatives not included in operating income $ 5.4 $ 6.9 $ 14.9 $ 4.8 $ 3.2 $ 2.1 $ 0.9 $ (0.3) $ (0.2) Adjusted EBITDA2,3 $37.8 $45.6 $111.2 $69.1 $113.9 $88.7 $166.4 $94.2 $119.4 ADJUSTED EBITDA (Annual, in millions) FY2022 FY2023 FY2024 GAAP operating income (loss) $ 47.3 $ 57.3 $ 247.4 Depreciation and amortization $ 175.7 $ 162.4 $ 151.8 Share-based compensation expense1 $ 49.8 $ 39.7 $ 65.6 Certain impairments and other adjustments $ (9.7) $ 6.9 $ 1.2 Restructuring related charges $ 13.6 $ 43.8 $ 0.4 Realized gains (losses) on currency derivatives not included in operating income $ 4.4 $ 29.7 $ 2.4 Adjusted EBITDA 2,3 $281.1 $339.8 $468.7 ADJUSTED EBITDA (TTM, in millions) TTM Q4FY22 TTM Q1FY23 TTM Q2FY23 TTM Q3FY23 TTM Q4FY23 TTM Q1FY24 TTM Q2FY24 TTM Q3FY24 TTM Q4FY24 GAAP operating income (loss) $ 47.3 $ 12.4 $ (40.0) $ (23.8) $ 57.3 $ 109.4 $ 183.5 $ 234.9 $ 247.4 Depreciation and amortization $ 175.7 $ 172.2 $ 167.8 $ 163.9 $ 162.4 $ 161.4 $ 159.6 $ 157.0 $ 151.8 Share-based compensation expense1 $ 49.8 $ 49.2 $ 48.3 $ 42.8 $ 39.7 $ 41.7 $ 47.8 $ 58.9 $ 65.6 Certain impairments and other adjustments $ (9.7) $ (5.5) $ (3.7) $ (4.5) $ 6.9 $ 4.0 $ 5.5 $ 5.7 $ 1.2 Restructuring related charges $ 13.6 $ 15.7 $ 26.6 $ 53.3 $ 43.8 $ 41.6 $ 30.9 $ 0.9 $ 0.4 Realized gains (losses) on currency derivatives not included in operating income $ 4.4 $ 15.0 $ 29.2 $ 32.0 $ 29.7 $ 24.9 $ 10.9 $ 5.8 $ 2.4 Adjusted EBITDA2,3 $ 281.1 $ 259.0 $ 228.2 $ 263.7 $ 339.8 $ 383.0 $ 438.2 $ 463.2 $ 468.7 1SBC expense listed here excludes the portion included in restructuring-related charges to avoid double counting. 2This metric uses the definition of adjusted EBITDA as outlined above and therefore does not include the pro-forma impact of acquisitions, divestitures or the annualized benefit from actioned cost saving initiatives; however, our debt covenants allow for the inclusion of pro-forma impacts to adjusted EBITDA. 3Adjusted EBITDA includes 100% of the results of our consolidated subsidiaries and therefore does not give effect to adjusted EBITDA attributable to noncontrolling interests. This is to most closely align to our debt covenant and cash flow reporting. Values may not sum to total due to rounding. Page 28 of 31

ADJUSTED FREE CASH FLOW (Quarterly, in millions) Q4FY22 Q1FY23 Q2FY23 Q3FY23 Q4FY23 Q1FY24 Q2FY24 Q3FY24 Q4FY24 Net cash (used in) provided by operating activities $ 87.8 $ (25.3) $ 81.1 $ 12.6 $ 61.8 $ 42.3 $ 174.9 $ 8.4 $ 125.1 Purchases of property, plant and equipment $ (11.9) $ (11.8) $ (14.7) $ (11.0) $ (16.3) $ (22.6) $ (11.4) $ (10.5) $ (10.5) Capitalization of software and website development costs $ (15.4) $ (15.3) $ (13.9) $ (14.9) $ (13.6) $ (14.4) $ (13.9) $ (15.0) $ (14.9) Proceeds from sale of assets1 $ 10.3 $ 0.1 $ 1.2 $ 0.5 $ 2.8 $ 5.6 $ 0.4 $ 0.4 $ 17.1 Adjusted free cash flow1 $ 70.8 $ (52.2) $ 53.7 $ (12.8) $ 34.7 $ 10.9 $ 150.0 $ (16.6) $ 116.8 Reference: Value of finance leases $ 3.3 $ 2.4 $ 6.2 $ 5.8 $ 5.9 $ 0.4 $ 1.8 $ 2.2 $ 0.1 Cash restructuring payments $ — $ 7.9 $ 1.9 $ 5.0 $ 22.3 $ 5.7 $ 1.2 $ 0.5 $ 0.2 Cash paid for interest $ 34.6 $ 15.1 $ 35.8 $ 20.0 $ 43.2 $ 24.2 $ 42.4 $ 23.9 $ 41.7 Cash received for interest $ (1.0) $ (2.1) $ (3.0) $ (3.0) $ (3.4) $ (3.3) $ (2.8) $ (5.0) $ (3.0) Cash interest, net2 $ 33.6 $ 13.0 $ 32.8 $ 17.0 $ 39.7 $ 20.9 $ 39.6 $ 18.9 $ 38.8 ADJUSTED FREE CASH FLOW (Annual, in millions) FY2022 FY2023 FY2024 Net cash provided by operating activities $ 219.5 $ 130.3 $ 350.7 Purchases of property, plant and equipment $ (54.0) $ (53.8) $ (54.9) Capitalization of software and website development costs $ (65.3) $ (57.8) $ (58.3) Proceeds from sale of assets1 $ 14.5 $ 4.7 $ 23.6 Adjusted free cash flow1 $ 114.7 $ 23.4 $ 261.1 Reference: Value of finance leases $ 7.0 $ 20.3 $ 4.6 Cash restructuring payments $ 0.3 $ 37.1 $ 7.6 Cash paid for interest $ 98.1 $ 114.0 $ 132.3 Cash received for interest $ (3.2) $ (11.5) $ (14.2) Cash interest, net2 $ 94.9 $ 102.5 $ 118.1 1 During the quarter ended September 30, 2023 we revised our definition of adjusted free cash flow to include proceeds from the sale of assets. We have recast all periods in the chart above to include the benefit from the proceeds from sale of assets. 2 Cash interest, net is cash interest payments, partially offset by cash interest received on our cash and marketable securities. Prior to Q3 FY2023, we showed only the cash interest payments related to our borrowing activity in this chart in our earnings materials. We have recast all periods in the chart above to include the interest received. Values may not sum to total due to rounding. Page 29 of 31

ADJUSTED FREE CASH FLOW (TTM, in millions) TTM Q4FY22 TTM Q1FY23 TTM Q2FY23 TTM Q3FY23 TTM Q4FY23 TTM Q1FY24 TTM Q2FY24 TTM Q3FY24 TTM Q4FY24 Net cash provided by operating activities $ 219.5 $ 157.7 $ 95.5 $ 156.3 $ 130.3 $ 197.8 $ 291.6 $ 287.4 $ 350.7 Purchases of property, plant and equipment $ (54.0) $ (57.2) $ (54.0) $ (49.4) $ (53.8) $ (64.6) $ (61.2) $ (60.7) $ (54.9) Capitalization of software and website development costs $ (65.3) $ (65.0) $ (62.4) $ (59.6) $ (57.8) $ (56.9) $ (56.9) $ (57.0) $ (58.3) Proceeds from sale of assets1 $ 14.5 $ 13.0 $ 13.3 $ 12.2 $ 4.7 $ 10.2 $ 9.3 $ 9.2 $ 23.6 Adjusted free cash flow1 $ 114.7 $ 48.5 $ (7.6) $ 59.5 $ 23.4 $ 86.5 $ 182.8 $ 179.0 $ 261.1 Reference: Value of new finance leases $ 7.0 $ 8.6 $ 12.1 $ 17.7 $ 20.3 $ 18.3 $ 13.9 $ 10.3 $ 4.6 Cash restructuring payments $ 0.3 $ 8.2 $ 9.8 $ 14.9 $ 37.1 $ 34.9 $ 34.3 $ 29.7 $ 7.6 Cash paid for interest $ 98.1 $ 98.8 $ 99.2 $ 105.4 $ 114.0 $ 123.1 $ 129.8 $ 133.7 $ 132.3 Cash received for interest $ (3.2) $ (4.6) $ (6.9) $ (9.0) $ (11.5) $ (12.7) $ (12.6) $ (14.7) $ (14.2) Cash interest, net2 $ 94.9 $ 94.2 $ 92.4 $ 96.3 $ 102.5 $ 110.4 $ 117.2 $ 119.1 $ 118.1 1 During the quarter ended September 30, 2023 we revised our definition of adjusted free cash flow to include proceeds from the sale of assets. We have recast all periods in the chart above to include the benefit from the proceeds from sale of assets. 2 Cash interest, net is cash interest payments, partially offset by cash interest received on our cash and marketable securities. Prior to Q3 FY2023, we showed only the cash interest payments related to our borrowing activity in this chart in our earnings materials. We have recast all periods in the chart above to include the interest received. Values may not sum to total due to rounding. Page 30 of 31

ABOUT CIMPRESS: Cimpress plc (Nasdaq: CMPR) invests in and builds customer-focused, entrepreneurial, print mass-customization businesses for the long term. Mass customization is a competitive strategy which seeks to produce goods and services to meet individual customer needs with near mass production efficiency. Cimpress businesses include BuildASign, Drukwerkdeal, Exaprint, National Pen, Packstyle, Pixartprinting, Printi, VistaPrint and WIRmachenDRUCK. To learn more, visit https://www.cimpress.com. Cimpress and the Cimpress logo are trademarks of Cimpress plc or its subsidiaries. All other brand and product names appearing on this announcement may be trademarks or registered trademarks of their respective holders. CONTACT INFORMATION: Investor Relations: Media Relations: Meredith Burns Sara Litwiller ir@cimpress.com mediarelations@cimpress.com +1.781.652.6480 SAFE HARBOR STATEMENT: This earnings commentary contains statements about our future expectations, plans, and prospects of our business that constitute forward-looking statements for purposes of the safe harbor provisions under the Private Securities Litigation Reform Act of 1995, including our expectations for the growth and development of our businesses; revenue growth, adjusted EBITDA, income, adjusted free cash flow, net leverage, cash interest and taxes, net working capital, and other future financial results described under the Outlook, Leverage Policy and Capital Allocation section; our competitive position; our plans for capital allocations; and currency. Forward-looking projections and expectations are inherently uncertain, are based on assumptions and judgments by management, and may turn out to be wrong. Our actual results may differ materially from those indicated by the forward-looking statements in this document as a result of various important factors, including but not limited to flaws in the assumptions and judgments upon which our forecasts and estimates are based; the development, duration, and severity of supply chain constraints and inflation; costs and disruptions caused by acquisitions; our inability to make investments in our businesses and allocate our capital as planned or the failure of those investments and allocations to achieve the results we expect; the failure of the businesses we acquire or invest in to perform as expected; loss of key personnel or our inability to hire and retain talented personnel; our failure to develop and deploy our mass customization platform or the failure of the mass customization platform to drive the performance, efficiencies, and competitive advantage we expect; unanticipated changes in our markets, customers, or businesses; disruptions caused by political instability and war in Ukraine, Israel, or elsewhere; our failure to attract new customers and retain our current customers; our failure to manage the growth and complexity of our business; changes in the laws and regulations, or in the interpretation of laws and regulations, that affect our businesses; our ability to maintain compliance with our debt covenants and pay our debts when due; general economic conditions; and other factors described in our Form 10-K for the fiscal year ended June 30, 2023 and the other documents we periodically file with the U.S. SEC. In addition, the statements and projections in this quarterly earnings document represent our expectations and beliefs as of the date of this document, and subsequent events and developments may cause these expectations, beliefs, and projections to change. We specifically disclaim any obligation to update any forward-looking statements. These forward-looking statements should not be relied upon as representing our expectations or beliefs as of any date subsequent to the date of this document. Page 31 of 31