CIMPRESS plc (CMPR)

Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations

This Report contains forward-looking statements that involve risks and uncertainties. The statements contained in this Report that are not purely historical are forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934, including but not limited to our statements about the anticipated growth and development of our businesses and financial results, the impact of interest rate and currency fluctuations, the impact of U.S. tariffs (including potential changes in related trade policies and potential mitigation actions and related estimates, cost impacts, pricing changes and changes in customer demand), sources of liquidity to fund future operations, future payment terms with suppliers, the timing of adoption of certain accounting standards, legal proceedings, our ability to prevail in our appeal of an adverse land duty tax assessment, indefinitely reinvested earnings, unrecognized tax benefits, our effective tax rate, and sufficiency of our tax reserves. Without limiting the foregoing, the words “may,” “should,” “could,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” "assume," “designed,” “potential,” "possible," “continue,” “target,” “seek,” "likely," "will" and similar expressions are intended to identify forward-looking statements. All forward-looking statements included in this Report are based on information available to us up to, and including, the date of this document, and we disclaim any obligation to update any such forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements 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 fluctuating inflation; 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; costs and disruptions caused by acquisitions and minority investments; the failure of businesses we acquire or invest in to perform as expected; loss of key personnel or our inability to recruit 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 geopolitical events or political instability and war in Ukraine, Israel, the Middle East, or elsewhere; changes in governmental policies, laws, and regulations that affect our businesses, or in their enforcement or interpretation, including related to import tariffs; our failure to manage the growth and complexity of our business; our failure to maintain compliance with the covenants in our debt documents or to pay our debts when due; competitive pressures; general economic conditions; and other factors described in Item 1A (Risk Factors) of our Annual Report on Form 10-K for the 2025 fiscal year, this Quarterly Report on Form 10-Q and subsequent documents we periodically file with the SEC.

Executive Overview

Cimpress is a strategically focused collection of businesses that specialize in print mass customization, through which we deliver large volumes of individually small-sized customized orders of printed materials and promotional products. Our products and services include a broad range of marketing materials, business cards, signage, promotional products, logo apparel, packaging, books and magazines, wall decor, photo merchandise, invitations and announcements, design and digital marketing services, and other categories. Mass customization is a core element of the business model of each Cimpress business and is a competitive strategy which seeks to produce goods and services to meet individual customer needs with near mass production efficiency.

As of March 31, 2026, we have numerous operating segments under our management reporting structure that are reported in the following five reportable segments: VistaPrint, PrintBrothers, The Print Group, National Pen, and All Other Businesses. For purposes of measuring and reporting our segment financial performance, we made updates to our previously implemented methodology for inter-segment transactions during the first quarter of fiscal 2026. These transactions occur when one Cimpress business buys from or sells to another Cimpress business. Under the updated methodology, a merchant business (the buyer) is cross charged the variable cost of fulfillment that includes labor, materials and shipping costs, which excludes the previously included overhead allocation. We also updated our internal organizational structure, which included the transfer of two teams from our VistaPrint reportable segment into our central functions. We have recast the prior periods presented for segment revenue and segment EBITDA for both changes to ensure comparability with the current fiscal year. These changes have no impact on our consolidated financial results. Refer to Note 11 in our accompanying consolidated financial statements for additional information relating to our reportable segments and our segment financial measures.

Financial Summary

The primary financial metric by which we set quarterly and annual budgets both for individual businesses and Cimpress wide is our adjusted free cash flow before net cash interest payments; however, in evaluating the financial condition and operating performance of our business, management considers a number of metrics

29

including revenue growth, constant-currency revenue growth, organic constant-currency revenue growth (which excludes the impact of acquisitions/divestitures), operating income, net income, adjusted EBITDA, cash flow from operations, and adjusted free cash flow. Reconciliations of our non-GAAP financial measures are included within the "Consolidated Results of Operations" and "Additional Non-GAAP Financial Measures" sections of Management's Discussion and Analysis. A summary of these key financial metrics for the three and nine months ended March 31, 2026 as compared to the three and nine months ended March 31, 2025 follows:

Third Quarter Fiscal Year 2026

•Revenue increased by 12% to $886.2 million.

•Organic constant-currency revenue growth (a non-GAAP financial measure) was 4%.

•Operating income increased by $8.6 million to $49.2 million.

•Net income increased by $22.7 million to $14.6 million.

•Adjusted EBITDA (a non-GAAP financial measure) increased by $9.8 million to $100.5 million.

•Diluted net income per share attributable to Cimpress plc increased by $0.88 to $0.55.

Year to Date Fiscal Year 2026

•Revenue increased by 10% to $2,791.7 million.

•Organic constant-currency revenue growth (a non-GAAP financial measure) was 4%.

•Operating income increased by $25.4 million to $186.2 million.

•Net income increased by $29.4 million to $70.7 million.

•Adjusted EBITDA (a non-GAAP financial measure) increased by $27.4 million to $338.1 million.

•Diluted net income per share attributable to Cimpress plc increased by $1.25 to $2.81.

•Cash provided by operating activities decreased by $17.4 million to $173.2 million.

•Adjusted free cash flow (a non-GAAP financial measure) decreased by $25.2 million to $52.0 million.

For the three and nine months ended March 31, 2026, the increases in reported consolidated revenue were driven by external revenue growth across all of our reportable segments, as well as currency benefits and the addition of revenue from a recent tuck-in acquisition in our PrintBrothers reportable segment. The largest contributor of the organic constant-currency revenue growth was our VistaPrint business, driven by growth across all regions. Revenue growth continued to be strong across our assortment of elevated products.

The increases to operating income of $8.6 million and $25.4 million during the three and nine months ended March 31, 2026, respectively, were primarily driven by gross profit growth due to the revenue growth discussed above, cost improvements, benefits from currency, and a tuck-in acquisition. Gross profit improved despite an increase year over year of $3.6 million and $5.0 million, respectively, of net start-up costs, including the effect of depreciation expense, associated with the expansion of our North America production network. This gross profit growth was partially offset by increases to operating expenses during the three and nine months ended March 31, 2026.

Net income increased $22.7 million and $29.4 million during the three and nine months ended March 31, 2026, respectively, as compared to the prior-year periods. Both periods were partly impacted by volatility from higher unrealized hedging gains, as well as the impact of the operating income increases described above, and lower interest expenses.

Adjusted EBITDA increased by $9.8 million and $27.4 million during the three and nine months ended March 31, 2026, respectively, for similar reasons as the increase in operating income as described above, as well as $2.7 million and $9.7 million in year-over-year currency benefits, respectively. A tuck-in acquisition within the PrintBrothers reportable segment contributed an immaterial amount and $1.3 million to adjusted EBITDA for the three and nine months ended March 31, 2026, respectively. Adjusted EBITDA improved despite an increase year over year of $3.3 million and $5.2 million, respectively, of net start-up costs, excluding the effect of depreciation expense, associated with the expansion of our North America production network.

During the nine months ended March 31, 2026, cash from operations decreased $17.4 million year over year, driven by less favorable changes in net working capital year over year of $36.9 million, primarily due to timing items and unfavorable currency movements, as well as higher cash taxes, which were partially offset by the net income increase described above.

30

Adjusted free cash flow decreased by $25.2 million for the nine months ended March 31, 2026, primarily driven by the decrease in cash flow from operations as described above. Adjusted free cash flow was also impacted by a $6.3 million increase in capital expenditures mainly driven by the expansion of our North America production network, and a $2.5 million increase in capitalized software and website development costs, primarily driven by investments in our mass customization platform and related technology enhancements.

U.S. Tariffs

The U.S. tariff environment remains fluid. Cimpress businesses operate in the U.S., and we maintain fulfillment operations for U.S. customers in multiple locations across the U.S., Canada, and Mexico. During the three months ended March 31, 2026, the legal framework for U.S. tariffs was significantly altered by judicial and executive actions. On February 20, 2026, the U.S. Supreme Court invalidated using the International Emergency Economic Powers Act (IEEPA) as a basis to impose the broad tariffs that had been in place since May 2025. Following this ruling, the IEEPA-based duties were terminated and replaced, effective February 24, 2026, with a 10% global tariff under Section 122 of the Trade Act of 1974. By statute, this Section 122 surcharge is temporary and is currently scheduled to expire in July 2026 unless extended by Congress or replaced by other trade measures. The U.S. government is currently investigating additional avenues to implement more permanent tariffs.

The primary impact of tariffs on Cimpress continues to be for promotional products that we source from China and several other countries. To date, we have continued to minimize most imp

[Excerpt truncated for page length; source filing is linked above.]

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

This Report contains forward-looking statements that involve risks and uncertainties. The statements contained in this Report that are not purely historical are forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934, including but not limited to our statements about the anticipated growth and development of our businesses and financial results, the impact of interest rate and currency fluctuations, the impact of U.S. tariffs (including potential changes in related trade policies and potential mitigation actions and related estimates, cost impacts, pricing changes and changes in customer demand), sources of liquidity to fund future operations, future payment terms with suppliers, the timing of adoption of certain accounting standards, legal proceedings, our ability to prevail in our appeal of an adverse land duty tax assessment, indefinitely reinvested earnings, unrecognized tax benefits, our effective tax rate, and sufficiency of our tax reserves. Without limiting the foregoing, the words “may,” “should,” “could,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” "assume," “designed,” “potential,” "possible," “continue,” “target,” “seek,” "likely," "will" and similar expressions are intended to identify forward-looking statements. All forward-looking statements included in this Report are based on information available to us up to, and including the date of this document, and we disclaim any obligation to update any such forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements 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, severity, and duration of supply chain constraints and fluctuating inflation; our inability to make investments in our business and allocate our capital as planned or the failure of those investments and allocations to achieve the results we expect; costs and disruptions caused by acquisitions and minority investments; the failure of businesses we acquire or invest in to perform as expected; loss of key personnel or our inability to recruit 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 geopolitical events or political instability and war in Ukraine, Israel, the Middle East or elsewhere; changes in governmental policies, laws and regulations, or in the enforcement or interpretation of governmental policies, laws and regulations, that affect our businesses, including related to import tariffs; our failure to manage the growth and complexity of our business; our failure to maintain compliance with the covenants in our debt documents or to pay our debts when due; competitive pressures; general economic conditions; and other factors described in Item 1A (Risk Factors) of this Report and the documents that we periodically file with the SEC. The Business section of this Report also contains estimates and other statistical data from research we conducted in August 2022 with a third-party research firm, and this data involves a number of assumptions and limitations and contains projections and estimates of the sizes of the opportunities of our markets that are subject to a high degree of uncertainty and should not be given undue weight.

Executive Overview

Cimpress helps millions of businesses build brands, stand out, and grow via customized physical marketing products and branded merchandise. Cimpress is the global leader in web-to-print mass customization, delivering high-quality, affordable custom products quickly and conveniently—even in low quantities. Our products and services include a broad range of marketing materials, business cards, signage, promotional products, logo apparel, packaging, books and magazines, wall decor, photo merchandise, invitations and announcements, design and digital marketing services, and other categories. Mass customization is a core element of the business model of each Cimpress business and is a competitive strategy that seeks to produce goods and services to meet individual customer needs with near mass production efficiency.

As of June 30, 2026, we have numerous operating segments under our management reporting structure that are reported in the following five reportable segments: VistaPrint, PrintBrothers, The Print Group, National Pen, and All Other Businesses. For purposes of measuring and reporting our segment financial performance, we made updates to our previously implemented methodology for inter-segment transactions during the first quarter of fiscal 2026. These transactions occur when one Cimpress business buys from or sells to another Cimpress business. Under the updated methodology, a merchant business (the buyer) is cross charged the variable cost of fulfillment that includes labor, materials and shipping costs, which excludes the previously included overhead allocation. We also updated our internal organizational structure, which included the transfer of two teams from our VistaPrint reportable segment into our central functions. We have recast the prior periods presented for segment revenue and segment EBITDA for both changes to ensure comparability with the current fiscal year. These changes have no impact on our consolidated financial results. Refer to Note 15 in our accompanying consolidated financial statements for additional information relating to our reportable segments and our segment financial measures.

28

Financial Summary

The primary financial metric by which we set quarterly and annual budgets both for individual businesses and Cimpress wide is our adjusted free cash flow before net cash interest payments; however, in evaluating the financial condition and operating performance of our business, management considers a number of metrics including revenue growth, constant-currency revenue growth, organic constant-currency revenue growth (which excludes the impact of acquisitions/divestitures), operating income, net income, adjusted EBITDA, cash flow from operations, and adjusted free cash flow. Reconciliations of our non-GAAP financial measures are included within the "Consolidated Results of Operations" and "Additional Non-GAAP Financial Measures" sections of Management's Discussion and Analysis. A summary of these key financial metrics for the year ended June 30, 2026 as compared to the year ended June 30, 2025 follows:

Fiscal Year 2026

•Revenue increased by 10% to $3,736.6 million.

•Organic constant-currency revenue growth (a non-GAAP financial measure) was 4%.

•Operating income increased by $24.8 million to $251.0 million.

•Net income increased by $84.3 million to $97.1 million.

•Adjusted EBITDA (a non-GAAP financial measure) increased by $25.3 million to $458.5 million.

•Diluted net income per share attributable to Cimpress plc increased by $3.21 to $3.79.

•Cash provided by operating activities decreased by $14.4 million to $283.7 million.

•Adjusted free cash flow (a non-GAAP financial measure) decreased by $25.6 million to $122.4 million.

For the year ended June 30, 2026, the increase in reported consolidated revenue was driven by external revenue growth across all of our reportable segments, as well as currency benefits and the addition of revenue from recent tuck-in acquisitions in our PrintBrothers and The Print Group reportable segments. The largest contributor of the organic constant-currency revenue growth was our VistaPrint business, driven by growth across all regions. Revenue growth continued to be strong across our assortment of elevated products.

The increase to operating income of $24.8 million during the year ended June 30, 2026, was primarily driven by organic gross profit growth due to the revenue growth discussed above, cost improvements, and benefits from currency. Gross profit grew despite $13.8 million of additional costs from investments in the expansion of our North America production network that include start-up costs, the reversal of Canadian duty drawback receivables of $4.7 million following unfavorable trade rulings, and inventory write downs of $1.8 million, partially offset by the benefit from U.S. tariff refunds of $6.9 million that were recognized during the fourth quarter of the current fiscal year. This gross profit growth was partially offset by increases in advertising costs and operating expenses during the year ended June 30, 2026.

Net income increased $84.3 million during the year ended June 30, 2026, as compared to the prior fiscal year. The net income increase was driven by the operating income growth described above, as well as higher unrealized hedging gains and lower interest and income tax expenses.

Adjusted EBITDA increased by $25.3 million during the year ended June 30, 2026, for similar reasons as the increase in operating income as described above, as well as $10.1 million in year-over-year currency benefits. Tuck-in acquisitions within the PrintBrothers and The Print Group reportable segments contributed $1.4 million to adjusted EBITDA, net of transaction-related costs, for the year ended June 30, 2026.

During the year ended June 30, 2026, cash from operations decreased $14.4 million year over year, driven by an increase in cash tax payments of $25.4 million, as well as a less favorable change in net working capital year over year that was influenced by increases in inventory and timing items, and an increase in restructuring payments of $5.2 million. These items were partially offset by the net income increase described above.

Adjusted free cash flow decreased by $25.6 million for the year ended June 30, 2026, primarily driven by the decrease in cash flow from operations as described above. Adjusted free cash flow was also impacted by a $11.2 million increase in capital expenditures mainly driven by the expansion of our North America production network, and a $3.0 million increase in capitalized software and website development costs, primarily driven by investments in our mass customization platform and related technology enhancements.

Refer to the "Additional Non-GAAP Financial Measures" section of Management's Discussion and Analysis for the reconciliation of our non-GAAP financial measures.

29

U.S. Tariffs

The U.S. tariff environment remains volatile. Cimpress businesses operate in the U.S., and we maintain fulfillment operations for U.S. customers in multiple locations across the U.S., Canada, and Mexico. On February 20, 2026, the U.S. Supreme Court invalidated using the International Emergency Economic Powers Act (IEEPA) as a basis to impose the broad tariffs that had been in place since May 2025. Following this ruling, the IEEPA-based invalidated duties were replaced, effective February 24, 2026, with a 10% global tariff under Section 122 of the Trade Act of 1974. By statute, this Section 122 surcharge expired on July 24, 2026. On July 24, 2026, the U.S. government implemented broad-based Section 301 tariffs of 10% to 12.5% that replaced the 10% global rate that expired the same day. Also, a 50% tariff on certain Canadian goods under Section 338 was announced to take effect on August 19, 2026. Our initial assessment is that these would affect a small portion of products fulfilled in Canada for U.S. customers, and we are actively operationalizing supply chain and fulfillment adjustments to mitigate a substantial portion of any prospective cost impact.

The primary impact of tariffs on Cimpress continues to be for promotional products that we source from China a

[Excerpt truncated for page length; the complete text is on the linked full-MD&A page.]