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Summary of Significant Accounting Policies Summary of Significant Accounting Principles (Tables)
12 Months Ended
Jun. 30, 2021
Accounting Policies [Abstract]  
Interest and Other Income
The following table summarizes the components of other (expense) income, net:
 Year Ended June 30,
202120202019
(Losses) gains on derivatives not designated as hedging instruments (1) $(20,728)$20,564 $23,494 
Currency-related gains (losses), net (2)8,523 2,309 2,506 
Other gains370 476 
Total other (expense) income, net$(11,835)$22,874 $26,476 
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(1) Primarily relates to both realized and unrealized gains and losses on derivative currency forward and option contracts and interest rate swaps not designated as hedging instruments, including losses of $3,422 for the year ended June 30, 2021, related to certain interest rate swap contracts that were de-designated from hedge accounting during the year due to their ineffectiveness, which had an immaterial impact in the comparative periods. As of June 30, 2021 we have redesignated several of our previously dedesignated hedge contracts. Refer to Note 4 for additional information.
(2) We have significant non-functional currency intercompany financing relationships that we may change at times and are subject to currency exchange rate volatility. The currency-related (losses) gains, net are primarily driven by this intercompany activity for the periods presented. In addition, we have certain cross-currency swaps designated as cash flow hedges which hedge the remeasurement of certain intercompany loans; both are presented in the same component above. Unrealized losses related to cross-currency swaps were $7,211 for the year ended
June 30, 2021 as compared to unrealized gains of $929 for the year ended June 30, 2020, and unrealized losses of $3,484 for the year ended June 30, 2019.
Schedule of Weighted Average Number of Shares
The following table sets forth the reconciliation of the weighted-average number of ordinary shares:
 Year Ended June 30,
 202120202019
Weighted average shares outstanding, basic25,996,572 27,180,744 30,786,349 
Weighted average shares issuable upon exercise/vesting of outstanding share options/RSUs/warrants (1)— 592,542 876,356 
Shares used in computing diluted net (loss) income per share attributable to Cimpress plc25,996,572 27,773,286 31,662,705 
Weighted average anti-dilutive shares excluded from diluted net (loss) income per share attributable to Cimpress plc (2)494,329 1,325 — 
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(1) In the periods in which a net loss is recognized, the impact of share options, RSUs and warrants is not included as they are anti-dilutive.
(2) On May 1, 2020, we entered into a financing arrangement with Apollo Global Management, Inc., which included 7-year warrants with a strike price of $60 that have a potentially dilutive impact on our weighted average shares outstanding. For the years ended June 30 2021 and 2020, the weighted average anti-dilutive effect of the warrants was 368,933 and 73,719 shares, respectively. Refer to Note 10 for additional details about the arrangement.
Debt Securities, Held-to-maturity
The following is a summary of the held-to-maturity securities by type as of June 30, 2021 and as of June 30, 2020 we held no marketable securities:

Amortized costUnrealized lossesFair value
June 30, 2021
Commercial paper$74,463 $(28)$74,435 
Corporate debt securities128,498 (147)128,351 
Total$202,961 $(175)$202,786 

The following table summarizes the net carrying amount and fair value of the held-to maturity securities by contractual maturity.
Amortized costFair value
Due within one year or less
Commercial paper and corporate debt securities$152,248 $152,163 
Due after one year through two years
Corporate debt securities50,713 50,623 
Total$202,961 $202,786