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Summary of Significant Accounting Policies Summary of Significant Accounting Principles (Tables) | 6 Months Ended
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Dec. 31, 2022
Accounting Policies [Abstract] |
Debt Securities, Held-to-maturity | The following is a summary of the net carrying amount, unrealized gains, unrealized losses, and fair value of held-to-maturity securities by type and contractual maturity as of December 31, 2022 and June 30, 2022.
| December 31, 2022
| Amortized cost |  |  |  | Unrealized losses |  | Fair value
Due within one year or less: |  |  |  |  |  |  |
Commercial paper | $ | 40,985 |  |  |  |  | $ | (227) |  |  | $ | 40,758 |
Corporate debt securities | 39,821 |  |  |  |  | (304) |  |  | 39,517 |
U.S. government securities | 4,264 |  |  |  |  | (66) |  |  | 4,198 |
Total due within one year or less | 85,070 |  |  |  |  | (597) |  |  | 84,473 |
Due between one and two years: |  |  |  |  |  |  |
Corporate debt securities | 12,144 |  |  |  |  | (253) |  |  | 11,891 |
U.S. government securities | 4,963 |  |  |  |  | (80) |  |  | 4,883 |
Total due within between one and two years | 17,107 |  |  |  |  | (333) |  |  | 16,774 |
Total held-to-maturity securities | $ | 102,177 |  |  |  |  | $ | (930) |  |  | $ | 101,247 |
| June 30, 2022
| Amortized cost |  | Unrealized losses |  |  |  | Fair value
Due within one year or less: |  |  |  |  |  |  |
Corporate debt securities | $ | 49,952 |  |  | $ | (546) |  |  |  |  | $ | 49,406 |
Total held-to-maturity securities | $ | 49,952 |  |  | $ | (546) |  |  |  |  | $ | 49,406 |
Interest and Other Income | The following table summarizes the components of other (expense) income, net:
| Three Months Ended December 31, |  | Six Months Ended December 31,
| 2022 |  | 2021 |  | 2022 |  | 2021 |  |
(Losses) gains on derivatives not designated as hedging instruments (1) | $ | (24,196) |  |  | $ | 6,481 |  |  | $ | 4,449 |  |  | $ | 19,808 |  |  |
Currency-related gains, net (2) | 6,227 |  |  | 5,551 |  |  | 6,030 |  |  | 5,874 |  |  |
Other gains (losses) | 577 |  |  | 807 |  |  | (474) |  |  | 327 |  |  |
Total other (expense) income, net | $ | (17,392) |  |  | $ | 12,839 |  |  | $ | 10,005 |  |  | $ | 26,009 |  |  |
_____________________ (1) Includes realized and unrealized gains and losses on derivative currency forward and option contracts not designated as hedging instruments, as well as the ineffective portion of certain interest rate swap contracts that were de-designated from hedge accounting in the prior periods. For contracts not designated as hedging instruments, we realized gains of $16,368 and $30,988 for the three and six months ended December 31, 2022, and losses of $746 and $4,418 for the three and six months ended December 31, 2021. Refer to Note 4 for additional details relating to our derivative contracts. (2) Currency-related gains, net primarily relates to significant non-functional currency intercompany financing relationships that we may change at times and are subject to currency exchange rate volatility. In addition, we have a cross-currency swap designated as a cash flow hedge which hedges the remeasurement of an intercompany loan. Refer to Note 4 for additional details relating to this cash flow hedge.
Schedule of Weighted Average Number of Shares | The following table sets forth the reconciliation of the weighted-average number of ordinary shares:
| Three Months Ended December 31, |  | Six Months Ended December 31,
| 2022 |  | 2021 |  | 2022 |  | 2021 |  |
Weighted average shares outstanding, basic | 26,234,747 |  |  | 26,096,786 |  |  | 26,206,782 |  |  | 26,084,518 |  |  |
Weighted average shares issuable upon exercise/vesting of outstanding share options/RSUs/warrants (1) | — |  |  | 305,917 |  |  | — |  |  | 408,740 |  |  |
Shares used in computing diluted net (loss) income per share attributable to Cimpress plc | 26,234,747 |  |  | 26,402,703 |  |  | 26,206,782 |  |  | 26,493,258 |  |  |
Weighted average anti-dilutive shares excluded from diluted net (loss) income per share attributable to Cimpress plc (1)(2) | 3,286,936 |  |  | 567,220 |  |  | 2,987,875 |  |  | 292,834 |  |  |
___________________ (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 three and six months ended December 31, 2022, the weighted average anti-dilutive effect of the warrants was 1,055,377 shares in both periods, and 281,884 and 345,722 shares for the three and six months ended December 31, 2021, respectively.

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