Keane Robert S

SEC source: 0001262976-21-000012 · wf-form4_161349830337557.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,668

Underlying: Ordinary Shares · 58,668 shares

Expires 2031-02-15

F1 · security: Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the compound annual growth rate (CAGR) of the three-year moving average daily price per share of Cimpress' ordinary shares (3YMA). The service-based vesting condition is that 25% of the original number of PSUs vest on each June 30 of 2021 through 2024 so long as the reporting person continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

F2 · derivative.exercise_price: This dollar amount is the 3YMA on the date of grant, which is the baseline against which the CAGR of the 3YMA will be measured.

F1 · derivative.exercise_date: Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the compound annual growth rate (CAGR) of the three-year moving average daily price per share of Cimpress' ordinary shares (3YMA). The service-based vesting condition is that 25% of the original number of PSUs vest on each June 30 of 2021 through 2024 so long as the reporting person continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-20-000097 · wf-form4_160562225766574.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,123

Underlying: Ordinary Shares · 1,123 shares

Expires 2030-11-15

F1 · security: Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the compound annual growth rate (CAGR) of the three-year moving average daily price per share of Cimpress' ordinary shares (3YMA). The service-based vesting condition is that 25% of the original number of PSUs vest on each November 24 of 2021 through 2024 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

F2 · derivative.exercise_price: This dollar amount is the 3YMA on the date of grant, which is the baseline against which the CAGR of the 3YMA will be measured.

F1 · derivative.exercise_date: Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the compound annual growth rate (CAGR) of the three-year moving average daily price per share of Cimpress' ordinary shares (3YMA). The service-based vesting condition is that 25% of the original number of PSUs vest on each November 24 of 2021 through 2024 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001209191-20-048751 · doc4.xml · derivative · entry 8

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: $.01 PV Common Stock · 5,600 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_price: Each restricted stock unit represents the right to receive, at settlement, one share of common stock.

F5 · derivative.exercise_date: These restricted stock units granted on August 28, 2020.

F5 · derivative.expiration_date: These restricted stock units granted on August 28, 2020.

SEC source: 0001209191-20-048751 · doc4.xml · nonDerivative · entry 1

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,600

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001209191-20-048244 · doc4.xml · nonDerivative · entry 5

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Note

Disclosed balance after: 448,199

F3 · price: As a result of estate planning transactions, 5096 Saranac LLC made an in-kind distribution of the 85,695 shares of Common Stock and 1,409,614 shares of Class B Common Stock held by it to its members, including 373,827 shares of Class B Common Stock to Boston & Saranac. The other shares were distributed in-kind to the Sibling Trusts.

F3 · ownership.nature: As a result of estate planning transactions, 5096 Saranac LLC made an in-kind distribution of the 85,695 shares of Common Stock and 1,409,614 shares of Class B Common Stock held by it to its members, including 373,827 shares of Class B Common Stock to Boston & Saranac. The other shares were distributed in-kind to the Sibling Trusts.

F4 · ownership.nature: The direct owner is Boston & Saranac LLC.

SEC source: 0001209191-20-048244 · doc4.xml · nonDerivative · entry 4

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Note

Disclosed balance after: 0

F3 · price: As a result of estate planning transactions, 5096 Saranac LLC made an in-kind distribution of the 85,695 shares of Common Stock and 1,409,614 shares of Class B Common Stock held by it to its members, including 373,827 shares of Class B Common Stock to Boston & Saranac. The other shares were distributed in-kind to the Sibling Trusts.

F2 · ownership.nature: The direct owner is 5096 Saranac LLC, a Delaware limited liability company which was established by a trust of the Reporting Persons father, Kevin T. Keane. As a result of estate planning transactions, the direct owner is now owned 25% by Boston & Saranac LLC, a Delaware limited liability company("Boston & Saranac"), and 75% by limited liability companies owned by trusts for the benefit of the siblings or descendants of siblings of the Reporting Person ("Sibling Trusts"). Boston & Saranac is 100% owned by a trust whose beneficiaries are the Reporting Person and his spouse.

F3 · ownership.nature: As a result of estate planning transactions, 5096 Saranac LLC made an in-kind distribution of the 85,695 shares of Common Stock and 1,409,614 shares of Class B Common Stock held by it to its members, including 373,827 shares of Class B Common Stock to Boston & Saranac. The other shares were distributed in-kind to the Sibling Trusts.

SEC source: 0001209191-20-048244 · doc4.xml · nonDerivative · entry 3

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Note

Disclosed balance after: 1,409,614

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each share of Class B Stock is convertible at any time, at the option of the holder, into one fully paid and non-assessable share of Common Stock.

F2 · ownership.nature: The direct owner is 5096 Saranac LLC, a Delaware limited liability company which was established by a trust of the Reporting Persons father, Kevin T. Keane. As a result of estate planning transactions, the direct owner is now owned 25% by Boston & Saranac LLC, a Delaware limited liability company("Boston & Saranac"), and 75% by limited liability companies owned by trusts for the benefit of the siblings or descendants of siblings of the Reporting Person ("Sibling Trusts"). Boston & Saranac is 100% owned by a trust whose beneficiaries are the Reporting Person and his spouse.

SEC source: 0001209191-20-048244 · doc4.xml · nonDerivative · entry 2

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Note

Disclosed balance after: 0

F3 · price: As a result of estate planning transactions, 5096 Saranac LLC made an in-kind distribution of the 85,695 shares of Common Stock and 1,409,614 shares of Class B Common Stock held by it to its members, including 373,827 shares of Class B Common Stock to Boston & Saranac. The other shares were distributed in-kind to the Sibling Trusts.

F2 · ownership.nature: The direct owner is 5096 Saranac LLC, a Delaware limited liability company which was established by a trust of the Reporting Persons father, Kevin T. Keane. As a result of estate planning transactions, the direct owner is now owned 25% by Boston & Saranac LLC, a Delaware limited liability company("Boston & Saranac"), and 75% by limited liability companies owned by trusts for the benefit of the siblings or descendants of siblings of the Reporting Person ("Sibling Trusts"). Boston & Saranac is 100% owned by a trust whose beneficiaries are the Reporting Person and his spouse.

F3 · ownership.nature: As a result of estate planning transactions, 5096 Saranac LLC made an in-kind distribution of the 85,695 shares of Common Stock and 1,409,614 shares of Class B Common Stock held by it to its members, including 373,827 shares of Class B Common Stock to Boston & Saranac. The other shares were distributed in-kind to the Sibling Trusts.

SEC source: 0001209191-20-048244 · doc4.xml · nonDerivative · entry 1

Keane Robert S · CIK 0001337084 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Note

Disclosed balance after: 85,695

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each share of Class B Stock is convertible at any time, at the option of the holder, into one fully paid and non-assessable share of Common Stock.

F2 · ownership.nature: The direct owner is 5096 Saranac LLC, a Delaware limited liability company which was established by a trust of the Reporting Persons father, Kevin T. Keane. As a result of estate planning transactions, the direct owner is now owned 25% by Boston & Saranac LLC, a Delaware limited liability company("Boston & Saranac"), and 75% by limited liability companies owned by trusts for the benefit of the siblings or descendants of siblings of the Reporting Person ("Sibling Trusts"). Boston & Saranac is 100% owned by a trust whose beneficiaries are the Reporting Person and his spouse.

SEC source: 0001262976-20-000061 · wf-form4_159771175137264.xml · derivative · entry 2

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 887

Underlying: Ordinary Shares · 887 shares

Expires 2030-08-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average of Cimpress' share price (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F2 · derivative.exercise_date: Each performance share unit (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the PSUs vest on each of September 30, 2020, December 31, 2020, March 31, 2021, and June 30, 2021 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on the vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-20-000061 · wf-form4_159771175137264.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 14,322

Underlying: Ordinary Shares · 14,322 shares

Expires 2030-08-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average of Cimpress' share price (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F2 · derivative.exercise_date: Each performance share unit (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the PSUs vest on each of September 30, 2020, December 31, 2020, March 31, 2021, and June 30, 2021 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on the vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001209191-20-035415 · doc4a.xml · nonDerivative · entry 4

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (2)

Disclosed balance after: 74,372

F2 · ownership.nature: The direct owner is Boston & Saranac.

SEC source: 0001209191-20-035415 · doc4a.xml · nonDerivative · entry 3

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (3)

Disclosed balance after: 0

F3 · ownership.nature: As a result of the same estate planning transaction in Note 1 above, 223,116 shares of Class B Stock have been transferred to entities 100% owned by trusts whose beneficiaries are the siblings or the descendants of siblings of the Reporting Person ("Sibling Trusts"). 74,372 shares of Class B Stock have been transferred to Boston & Saranac.

SEC source: 0001209191-20-035415 · doc4a.xml · nonDerivative · entry 2

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (2)

Disclosed balance after: 44,726

F2 · ownership.nature: The direct owner is Boston & Saranac.

SEC source: 0001209191-20-035415 · doc4a.xml · nonDerivative · entry 1

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (1)

Disclosed balance after: 2,222

F1 · ownership.nature: The direct owner is the Estate of Kevin T. Keane. The Reporting Person is one of multiple beneficiaries to a trust to be established by that estate. The entire amount of the estate's interest is reported on this form, however the Reporting Person's proportionate interest is below 25%. Shares held by the estate have been transferred to entities beneficially owned by descendants of Kevin T. Keane in an estate planning transactions. As a result, 134,178 Shares of Common Stock have been transferred to entities of which certain of the Reporting Persons's siblings are the primary beneficiary trusts. 44,726 shares of Common Stock have been transferred to Boston & Saranac LLC, a Delaware limited liability company 100% owned by a trust whose beneficiaries are the Reporting Person and his Spouse ("Boston & Saranac").

SEC source: 0001209191-20-035263 · doc4.xml · nonDerivative · entry 4

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (2)

Disclosed balance after: 74,372

F2 · ownership.nature: The direct owner is Boston & Saranac LLC, of which the Reporting Person and his spouse are the primary beneficiary trusts.

SEC source: 0001209191-20-035263 · doc4.xml · nonDerivative · entry 3

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (3) & (4)

Disclosed balance after: 1,495,340

F3 · ownership.nature: The direct owner is 5096 Saranac LLC, of which the Estate of Kevin T. Keane, the estate of the deceased father of this form's Reporting Person, was formerly the direct owner. The Reporting Person is one of multiple beneficiaries (and one of multiple trustees) to a trust to be established by that estate. The entire amount of the estate's interest is reported on this form, however the Reporting Person's proportionate interest is below 25%.

F4 · ownership.nature: 25% of the ownership of 5096 Saranac LLC has been transferred to Boston & Saranac LLC, of which the Reporting Person and his spouse are the primary beneficiary trusts, and the remaining 75% ownership of 5096 Saranac LLC has been transferred to entities of which certain other of the Reporting Person's siblings are the primary beneficiary trusts. 223,116 shares of Class B Stock have been transferred to entities of which certain of the Reporting Person's siblings are the primary beneficiary trusts. 74,372 shares of Class B Common Stock have been transferred to Boston & Saranac LLC, of which the Reporting Person and his spouse are the primary beneficiary trusts.

SEC source: 0001209191-20-035263 · doc4.xml · nonDerivative · entry 2

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (2)

Disclosed balance after: 44,726

F2 · ownership.nature: The direct owner is Boston & Saranac LLC, of which the Reporting Person and his spouse are the primary beneficiary trusts.

SEC source: 0001209191-20-035263 · doc4.xml · nonDerivative · entry 1

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · Note (1)

Disclosed balance after: 2,222

F1 · ownership.nature: The direct owner is the Estate of Kevin T. Keane, the father of this form's Reporting Person. The Reporting Person is one of multiple beneficiaries (and one of multiple trustees) to a trust to be established by that estate. The entire amount of the estate's interest is reported on this form, however the Reporting Person's proportionate interest is below 25%. 134,178 Shares of Common Stock have been transferred to entities of which certain of the Reporting Persons's siblings are the primary beneficiary trusts. 44,726 shares of Common Stock have been transferred to Boston & Saranac LLC, of which the Reporting Person and his spouse are the primary beneficiary trusts.

SEC source: 0001209191-20-014522 · doc4.xml · derivative · entry 15

Keane Robert S · CIK 0001337084 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,600

Underlying: $.01 PV Common Stock · 5,600 shares

Expires not disclosed

F3 · derivative.exercise_price: Each restricted stock unit represents the right to receive, at settlement, one share of common stock.

F4 · derivative.exercise_date: These restricted stock units are scheduled to vest 100% on August 28, 2020.

F4 · derivative.expiration_date: These restricted stock units are scheduled to vest 100% on August 28, 2020.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · derivative · entry 20

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 112,231 shares

Expires 2020-05-04

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_price: The option exercise price per share is $50.00, which is at least 33% higher than the closing price of Cimpress' ordinary shares on the NASDAQ Global Select Market on the date of grant.

F7 · derivative.exercise_price: $0.0001 added to exercise price solely to differentiate the securities on this Form 4.

F5 · derivative.exercise_date: The share options vest over a seven-year period as follows: 6.25% of the original number of ordinary shares subject to the share options vest on the Exercisable Date in Table II. The remaining ordinary shares vest on a quarterly basis over the subsequent six years in tranches ranging from 1.56% to 10.94% of the original number of ordinary shares subject to the option.

F6 · derivative.exercise_date: In addition to the vesting restrictions referred to in footnote 5 above, these share options are exercisable only on days when the high price per share of Cimpress' ordinary shares on NASDAQ equals or exceeds $75.00.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · derivative · entry 19

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 500,000 shares

Expires 2020-05-04

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_price: The option exercise price per share is $50.00, which is at least 33% higher than the closing price of Cimpress' ordinary shares on the NASDAQ Global Select Market on the date of grant.

F5 · derivative.exercise_date: The share options vest over a seven-year period as follows: 6.25% of the original number of ordinary shares subject to the share options vest on the Exercisable Date in Table II. The remaining ordinary shares vest on a quarterly basis over the subsequent six years in tranches ranging from 1.56% to 10.94% of the original number of ordinary shares subject to the option.

F6 · derivative.exercise_date: In addition to the vesting restrictions referred to in footnote 5 above, these share options are exercisable only on days when the high price per share of Cimpress' ordinary shares on NASDAQ equals or exceeds $75.00.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · derivative · entry 18

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 48,400 shares

Expires 2020-05-06

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: This option became exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares at the end of each successive three-month period thereafter.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · derivative · entry 17

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By The Eastern Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 500,000 shares

Expires 2020-05-04

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_price: The option exercise price per share is $50.00, which is at least 33% higher than the closing price of Cimpress' ordinary shares on the NASDAQ Global Select Market on the date of grant.

F7 · derivative.exercise_price: $0.0001 added to exercise price solely to differentiate the securities on this Form 4.

F5 · derivative.exercise_date: The share options vest over a seven-year period as follows: 6.25% of the original number of ordinary shares subject to the share options vest on the Exercisable Date in Table II. The remaining ordinary shares vest on a quarterly basis over the subsequent six years in tranches ranging from 1.56% to 10.94% of the original number of ordinary shares subject to the option.

F6 · derivative.exercise_date: In addition to the vesting restrictions referred to in footnote 5 above, these share options are exercisable only on days when the high price per share of Cimpress' ordinary shares on NASDAQ equals or exceeds $75.00.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · derivative · entry 16

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By The Eastern Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 500,000 shares

Expires 2020-05-04

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_price: The option exercise price per share is $50.00, which is at least 33% higher than the closing price of Cimpress' ordinary shares on the NASDAQ Global Select Market on the date of grant.

F5 · derivative.exercise_date: The share options vest over a seven-year period as follows: 6.25% of the original number of ordinary shares subject to the share options vest on the Exercisable Date in Table II. The remaining ordinary shares vest on a quarterly basis over the subsequent six years in tranches ranging from 1.56% to 10.94% of the original number of ordinary shares subject to the option.

F6 · derivative.exercise_date: In addition to the vesting restrictions referred to in footnote 5 above, these share options are exercisable only on days when the high price per share of Cimpress' ordinary shares on NASDAQ equals or exceeds $75.00.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · derivative · entry 15

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By The Eastern Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 48,400 shares

Expires 2020-05-06

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: This option became exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares at the end of each successive three-month period thereafter.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 8

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 573,935

F2 · shares: Of the 445,220 shares forfeited, 274,626 shares were forfeited as payment of the exercise price and 170,594 shares were forfeited as payment of the withholding taxes.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 7

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 1,019,155

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 6

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 906,924

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 5

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 406,924

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 4

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 573,975

F2 · shares: Of the 445,220 shares forfeited, 274,626 shares were forfeited as payment of the exercise price and 170,594 shares were forfeited as payment of the withholding taxes.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 3

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 1,019,195

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 2

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 906,964

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-20-000023 · wf-form4_158290700131582.xml · nonDerivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 406,964

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.

SEC source: 0001262976-19-000108 · wf-form4_157418182452292.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,119

Underlying: Ordinary Shares · 1,119 shares

Expires 2029-11-21

F1 · derivative.exercise_price: This dollar amount is the three-year moving average of the daily closing share price of Cimpress' ordinary shares (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F2 · derivative.exercise_date: Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each November 21 of 2020 through 2023 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-19-000076 · wf-form4_156624743877483.xml · derivative · entry 3

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 918

Underlying: Ordinary Shares · 918 shares

Expires 2029-08-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F3 · derivative.exercise_date: Each performance share unit (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each of September 30, 2019, December 31, 2019, March 31, 2020, and June 30, 2020 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on the vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-19-000076 · wf-form4_156624743877483.xml · derivative · entry 2

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 14,931

Underlying: Ordinary Shares · 14,931 shares

Expires 2029-08-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F3 · derivative.exercise_date: Each performance share unit (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each of September 30, 2019, December 31, 2019, March 31, 2020, and June 30, 2020 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on the vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-19-000076 · wf-form4_156624743877483.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 57,381

Underlying: Ordinary Shares · 57,381 shares

Expires 2029-08-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F2 · derivative.exercise_date: Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each June 30 of 2020 through 2023 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-19-000034 · wf-form4_155716358610315.xml · derivative · entry 12

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 73,014 shares

Expires 2019-05-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: The transactions reported on this Form 4 were effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2018.

F3 · derivative.exercise_date: This option became exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares at the end of each successive three-month period thereafter.

SEC source: 0001262976-19-000034 · wf-form4_155716358610315.xml · derivative · entry 11

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 0

Underlying: Ordinary Shares · 73,014 shares

Expires 2019-05-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: The transactions reported on this Form 4 were effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2018.

F3 · derivative.exercise_date: This option became exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares at the end of each successive three-month period thereafter.

SEC source: 0001262976-19-000034 · wf-form4_155716358610315.xml · nonDerivative · entry 4

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 367,024

F1 · kind: The transactions reported on this Form 4 were effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2018.

F2 · balance_after: Includes 36,875 shares held by RHS Holdings Incorporated, of which Eastern Irrevocable, LLC and Western Irrevocable, LLC are the sole shareholders.

SEC source: 0001262976-19-000034 · wf-form4_155716358610315.xml · nonDerivative · entry 3

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Western Irrevocable, LLC

Disclosed balance after: 414,244

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: The transactions reported on this Form 4 were effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2018.

F2 · balance_after: Includes 36,875 shares held by RHS Holdings Incorporated, of which Eastern Irrevocable, LLC and Western Irrevocable, LLC are the sole shareholders.

SEC source: 0001262976-19-000034 · wf-form4_155716358610315.xml · nonDerivative · entry 2

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 367,064

F1 · kind: The transactions reported on this Form 4 were effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2018.

F2 · balance_after: Includes 36,875 shares held by RHS Holdings Incorporated, of which Eastern Irrevocable, LLC and Western Irrevocable, LLC are the sole shareholders.

SEC source: 0001262976-19-000034 · wf-form4_155716358610315.xml · nonDerivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Indirect · By Eastern Irrevocable, LLC

Disclosed balance after: 414,284

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: The transactions reported on this Form 4 were effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2018.

F2 · balance_after: Includes 36,875 shares held by RHS Holdings Incorporated, of which Eastern Irrevocable, LLC and Western Irrevocable, LLC are the sole shareholders.

SEC source: 0001262976-19-000024 · wf-form4_155060484749631.xml · derivative · entry 3

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,116

Underlying: Ordinary Shares · 7,116 shares

Expires 2029-02-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F4 · derivative.exercise_date: Each PSU represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 50% of the original number of PSUs vest on March 31, 2019 and the remaining 50% vest on June 30, 2019 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-19-000024 · wf-form4_155060484749631.xml · derivative · entry 2

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,143

Underlying: Ordinary Shares · 1,143 shares

Expires 2029-02-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F3 · derivative.exercise_date: Each PSU represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each November 12 of 2019 through 2022 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-19-000024 · wf-form4_155060484749631.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · Director · CEO, Chairman

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 349

Underlying: Ordinary Shares · 349 shares

Expires 2029-02-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average (3YMA) on the date of grant, which is the baseline against which the compound annual growth rate (CAGR) of the 3YMA will be measured.

F2 · derivative.exercise_date: Each performance share unit (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 100% of the PSUs vest on June 30, 2019 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on the vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001262976-18-000064 · wf-form4_153445297518139.xml · derivative · entry 1

Keane Robert S · CIK 0001337084 · CEO, President · Chairman of Management Board

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,799

Underlying: Ordinary Shares · 58,799 shares

Expires 2028-08-15

F1 · derivative.exercise_price: This dollar amount is the three-year moving average daily price per share of Cimpress' ordinary shares ("3YMA") on the date of grant, which is the baseline against which the compound annual growth rate ("CAGR") of the 3YMA will be measured.

F2 · derivative.exercise_date: Each performance share unit (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each June 30 of 2019 through 2022 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds 11% on any of the sixth through tenth anniversaries of the grant date then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

SEC source: 0001209191-18-027654 · doc4.xml · derivative · entry 12

Keane Robert S · CIK 0001337084 · CEO, President · Chairman of Management Board

10b5-1 filing: Not disclosed

Ownership: Indirect · By The Western Irrevocable Trust

Disclosed balance after: 0

Underlying: Ordinary Shares · 166,659 shares

Expires 2018-05-02

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: This transaction was effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2017.

F2 · kind: Option exercised in full due to expiration on May 2, 2018.

F5 · derivative.exercise_date: This option became exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares at the end of each successive three-month period thereafter.

SEC source: 0001209191-18-027654 · doc4.xml · derivative · entry 11

Keane Robert S · CIK 0001337084 · CEO, President · Chairman of Management Board

10b5-1 filing: Not disclosed

Ownership: Indirect · By The Eastern Irrevocable Trust

Disclosed balance after: 0

Underlying: Ordinary Shares · 166,659 shares

Expires 2018-05-02

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: This transaction was effected pursuant to a 10b5-1 trading plan adopted by the reporting person on November 27, 2017.

F2 · kind: Option exercised in full due to expiration on May 2, 2018.

F5 · derivative.exercise_date: This option became exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares at the end of each successive three-month period thereafter.