Joint Share Ownership Agreement, dated January 21, 2020, between the Company, Dominic F. Silvester and Zedra Trust Company, as trustee

ENSTAR GROUP LIMITED, whose registered office is situated at Windsor Place, 3rd Floor, 22 Queen Street, Hamilton HM JX, Bermuda (Company No. 333-220889) (the "Company");

DOMINIC F. Silvester, Chief Executive Officer of Enstar Group Limited, care of 8^th Floor, One Creechurch Place, London, EC3A 5AY, United Kingdom (the "Executive"); and

ZEDRA TRUST COMPANY (GUERNSEY) LIMITED, whose registered office is at PO Box 341, Cambridge House, 3rd Floor, St Peter Port, Guernsey, GY1 3UW, Channel Islands (Company No. 24531) in its capacity as trustee of the Enstar Group Limited Employee Benefit Trust (the "Trustee").

The Company has invited the Executive, together with the Trustee, to subscribe jointly for the Shares under the terms of Schedule A to the rules of the Plan ("Schedule A") and subject to the terms of this Deed.

In accordance with Schedule A, the Trustee and the Executive have agreed to acquire distinct, concurrent beneficial interests in a single holding of Common Shares and hereby subscribe jointly for the Shares on the terms set out in this Deed. The Trustee shall hold the legal title of the Shares as nominee for the Trustee and the Executive.

The Interests are granted and each of the Executive and the Trustee shall acquire and hold the Executive Interest and the Trust Interest, respectively, subject to Schedule A.

In connection with the grant of the Interests, and the acquisition of the Shares, each of the Executive and Trustee makes the representations, warranties and covenants set forth in Appendix 1 hereto.

Capitalised terms used but not otherwise defined in this Deed have the meanings given to them in the Plan.

In this Deed, unless the context otherwise requires:

a material breach of the Company's or relevant Group Member's obligations under the Executive's employment agreement, provided that the Executive shall have given written notice thereof to the Company or relevant Group Member and the Company or relevant Group Member shall have failed to remedy the breach within 30 days;

the relocation of the Executive's principal business office outside of the United Kingdom, without the Executive's prior agreement; or

any material reduction in Executive's duties or authority;

20 January 2023; or

Any reference in this Deed to any enactment includes a reference to that enactment as from time to time modified, extended or re-enacted.

Expressions in italics and headings are for guidance only and do not form part of this Deed.

The Executive and the Trustee hereby subscribe, and the Company hereby agrees, subject to receipt of the amount in Clause 2.2 below, to issue, the Shares.

The Trustee agrees to pay the Total Subscription Price to the Company for the Trust Interest. The Executive is not required to pay any consideration for the Executive Interest. The Company will pay up to 60% of any employee income tax and employee social security contributions that arise as a result of the Grant and any tax liability arising on any such payment, up to a maximum aggregate amount of $5.3 million. The Executive will pay the Company, or agrees that the Company may deduct from amounts otherwise payable to the Executive, an amount equal to the balance of any and all employee income tax and employee social security contributions that arise as a result of the Grant.

The Executive and the relevant Group Member shall, on the date of this Deed and as a condition of the Grant being made, enter into a joint election in respect of any Grant in accordance with section 431 of ITEPA to disapply in full the restricted securities legislation contained in Chapter 2 of Part 7 of ITEPA in the form set out at Appendix 3 to this Deed.

The Executive Interest is as follows:

Less than the Hurdle, 0% of any value in the Shares; and

Equal to or greater than the Hurdle:

0% of any value in the Shares below the Grant Price; and

100% of any value in the Shares above the Grant Price.

Subject to Clause 9, neither the Executive nor the Trustee may call for a realisation of its Interest prior to the third anniversary of the Grant Date, other than in the event of a Change in Control.

The Executive Interest shall not be transferred, assigned, charged or otherwise disposed of except on death to the Executive's personal representatives or as otherwise permitted by this Deed or with the prior written agreement of the Company.

If the Executive attempts to transfer, assign, charge or otherwise dispose of the Executive Interest, except as permitted in this Deed or with the prior written agreement of the Company, the Trustee shall exercise the Trustee Option without notice.

The Trustee shall not dispose of the Shares without the prior written consent of the Executive other than:

following receipt of a notice pursuant to Clause 8.1;

in accordance with Clause 8.2;

following the exercise of the Trustee Option under Clause 9.1; or

pursuant to the acceptance of an offer in the event of a Change in Control.

Subject to Clauses 5, 6.3, 7 and 11.1, the Executive Interest shall Vest on the third anniversary of the Grant Date.

If the Market Price on the third anniversary of the Grant Date, or the Realisation Date, is less than the Hurdle, the Trustee shall exercise the Trustee Option.

20% of the Executive Interest shall be subject to the Performance Condition and that part of the Executive Interest shall Vest only to the extent that the Performance Condition has been satisfied. If the Performance Condition has not been met, the Trustee shall exercise the Trustee Option over the 20% of the Executive Interest that is unVested.

In the event the Executive experiences a Termination of Service for Cause, the Company shall notify the Trustee as soon as is practicable of such Termination of Service and the Trustee shall exercise the Trustee Option.

In the event the Executive experiences a Termination of Service by reason of death, disability, termination without Cause or resignation with Good Reason, the Executive Interest shall continue to be held by the Executive (or his/her estate or beneficiaries, as the case may be) on the terms of this Deed and, subject to Clause 11, Clauses 6 and 8 will continue to apply.

In the event the Executive experiences a Termination of Service for any other reason:

the Company shall notify the Trustee as soon as is practicable of such Termination of Service;

the Trustee shall exercise the Trustee Option in respect of the unVested part of the Executive Interest; and

the Vested part of the Executive Interest will continue to be held by the Executive on the terms of this Deed.

For a period of 3 months following the third anniversary of the Grant Date (the "Sale Period"), the Executive may, subject to Clauses 6.3 and 8.3, serve notice on the Trustee, by way of a notification in substantially the form set out in Appendix 4 to this Deed, requesting the Trustee to exchange the Executive's and Trustee's respective Interests unless the parties agree otherwise by mutual agreement, in which case the Executive may request the Trustee to sell the Shares or purchase the Executive Interest. Any fractional interest in Common Shares in respect of the Executive Interest will be rounded down to the nearest whole Common Share.

If the Executive does not serve such a notice during the Sale Period, the Trustee shall, subject to Clauses 6.3 and 8.3, as soon as reasonably practicable after the expiry of the Sale Period, exchange the Executive's and Trustee's respective Interests in the Shares so that, following such exchange, the Executive becomes the beneficial owner of 100% of that number of Shares whose market value is equal to the market value of the Executive Interest on that day of exchange unless the parties agree otherwise by mutual agreement, in which case the Trustee may:

sell the Shares and pay to the Executive a share of the sale proceeds of equal value to the Executive Interest at that time; or

purchase the Executive Interest for an amount equal to the then market value of the Executive Interest.

All exchanges, offers, sales and other transfers of the Shares will be subject to, and made in accordance with, the requirements of Appendix 1 to this Deed. Further, if the Executive and/or the Trustee is restricted from selling, dealing in or making arrangements to sell or deal in, the Shares by reason of any statutory, regulatory or other rule, by guidelines issued by the SEC, the NASDAQ or a similar regulatory body, or by the Company's

If the Executive serves a sale or purchase notice on the Trustee pursuant to Clause 8.1 or the Trustee sells the Shares or purchases the Executive Interest pursuant to Clause 8.2, the sale proceeds or purchase price payable to the Executive shall be deliverable in Common Shares.

If (i) in connection with a sale of Shares pursuant Clause 8.2, the Trustee proposes to publicly resell such Shares pursuant to Rule 144 and the Company believes the Trustee would be unable to sell all of the Shares proposed to be sold by it pursuant to Rule 144 without volume or manner-of-sale restrictions or (ii) following a payment of Common Shares to the Executive pursuant to Clause 8.4, the Company believes such Common Shares would be subject to holding period restrictions pursuant to Rule 144 following such payment, the Company shall file as promptly as practicable a secondary only registration statement on Form S-3 (or any successor form to Form S-3) promulgated under the Securities Act (which, if the Company is then a "well-known seasoned issuer" (as defined in Rule 405 under the Securities Act), shall be filed pursuant to General Instruction I.D of Form S-3 (an "Automatic Shelf Registration Statement")), registering the resale of such Shares or Common Shares, as applicable (the "Registrable Securities") (or, in the event that Form S-3 is not available for the registration of the resale of the Registrable Securities, another appropriate form reasonably acceptable to the Trustee or the Executive, as applicable (the "Registered Seller")), by the Registered Seller (the "Registration Statement"). The Company shall use its reasonable efforts (i) if the Registration Statement is not an Automatic Shelf Registration Statement, to cause the Registration Statement to become effective as promptly as practicable, (ii) to cause the Registration Statement to remain effective until the date on which the Registered Seller has disposed of all of the Registrable Securities and (iii) to undertake any additional actions reasonably necessary to maintain the availability of, and to facilitate the disposition by the Registered Seller of the Registrable Securities pursuant to, the Registration Statement. The Registered Seller agrees to cooperate with the Company as reasonably requested by the Company in connection with the preparation and filing of the Registration Statement, including furnishing to the Company such information regarding itself, the Common Shares in the Company held by it and the intended method of disposition of the Registrable Securities as shall be reasonably required to effect the registration of such Registrable Securities. The Company shall bear all expenses incurred in connection with the performance of its obligations under this Clause 8.5; provided, however, that the Company shall have no obligation to pay for any commissions or transfer taxes of the Registered Seller or the fees, disbursements or expenses of any counsel to the Registered Seller. The Company's obligations under this Clause 8.5 shall also apply to any shares in the capital of the Company issued or issuable with respect to the Registrable Securities as a result of any share split, share dividend, recapitalization, exchange or similar event.

The Executive grants the Trustee an option (the "Trustee Option") to acquire the whole or a portion of the Executive Interest for nil consideration in accordance with Clauses 5.3, 6.2, 6.3, 7.1 and 7.3.2.

In the event the Trustee exercises the Trustee Option, it shall serve on the Executive a notice of exercise in substantially the form set out in Appendix 5 to this Deed.

The Executive and Trustee hold voting rights, in respect of the Shares in the same proportions as their respective Interests. The Executive and Trustee, however, agree to waive their rights to vote in respect of the Shares.

Any dividend payable on the Shares will be distributed in proportion to the Executive Interest and the Trust Interest, as determined at the relevant dividend record date.

The Trustee, however, under the terms of Enstar Group Limited Employee Benefit Trust deed, waives its right to a dividend in respect of the Trust Interest. Any dividends payable in respect of the Executive Interest shall be paid (in cash) to the Trustee (net of any dividend withholding taxes) to hold for the Executive. The Trustee will subsequently pay to the Executive any proportion of the dividends representing his personal income tax liability in respect of the dividend paid. If the Executive realises value from the Executive Interest pursuant to Clauses 8.1, 8.2 or 11, the remaining dividend monies will be used to acquire additional Shares to be transferred to the Executive at that time. If the Executive does not realise value from the Executive Interest pursuant to

In the event of a Change in Control, subject to Clause 11.2:

the Executive Interest shall Vest in full and, in anticipation of that Vesting, the Executive may serve notice on the Trustee at any time before the Change in Control, but subject to and in accordance with, any terms of the Change in Control, requesting the Trustee to accept the offer or other event with respect to the Executive Interest; and

the Trustee will pay / deliver to the Executive any consideration received under the offer or other event (in cash or shares in the offeror company, depending on the form of consideration so received) after deduction of an amount equal to the value of the Trust Interest.

If the terms of the offer or other event include an opportunity to exchange Shares for equivalent shares in the offeror company, the Trustee and the Executive may agree with offeror to exchange the Shares for equivalent shares in the offeror company in which case, the Executive Interest shall not Vest and Clause 11.3 shall apply to any such exchange. If the Trustee, Executive and offeror agree to exchange the Shares for equivalent shares in the offeror company, the Executive appoints the Trustee as the Executive's attorney to enter into such arrangements as may be necessary or desirable to effect such exchange.

If the Shares are exchanged for shares in the offeror company under Clause 11.2, the replacement shares will be held jointly on the terms of this Deed as if they were Shares.

The rights and obligations of the Executive under the terms of his office or employment with any Group Member shall not be affected by this Deed.

If the Executive ceases to hold office or employment with a Group Member, a certificate issued by the Company as to the reason why the Executive ceased to be a director, officer or employee shall be conclusive for the purposes of the Grant and Executive Interest.

Save as set out in Clause 2.2, the Executive shall be responsible for, and indemnifies the Company and the Trustee against, all relevant employment taxes relating to the Executive Interest. A Group Company and/or the Trustee may withhold an amount equal to such relevant tax from any amounts due to the Executive (to the extent such withholding is lawful) and/or make any other arrangements as it considers appropriate to ensure recovery of such relevant taxes including, without limitation, the sale of sufficient Shares acquired pursuant to the Grant to realise an amount equal to the relevant taxes (and the payment of that amount to the relevant authorities in satisfaction of the relevant taxes).

The Executive acknowledges that there will be collection, processing and transfer of his personal data for any purpose relating to this Deed. This includes:

providing personal data to any Group Member and any third party such as the Trustee, registrars, brokers and any of their respective agents;

processing of personal data by any such Group Member or third party;

transferring personal data to a country outside the European Economic Area (including a country which does not have data protection laws equivalent to those prevailing in the European Economic Area); and

providing personal data to potential purchasers of the Company, the Executive's employer or the business in which the Executive works.

A notice or other communication under or in connection with this Deed (a "Notice") shall be in writing and delivered personally or sent by first class post or email to the party due to receive the Notice to the address set out above provided that if the Notice is delivered by email it must also be delivered by one of the other methods specified in this Clause 15.1.

Unless there is evidence that it was received earlier, a Notice is deemed given if:

delivered personally, when left at the address set out above;

sent by mail two Business Days after posting it;

sent by email, when the email is sent, provided that a copy of the Notice is sent by another method referred to in this Clause 15.2 within one Business Day of sending the email.

A variation of this Deed is valid only if it is in writing and signed by or on behalf of each party.

The failure to exercise or delay in exercising a right or remedy provided by this Deed or by law does not impair or constitute a waiver of the right or remedy or an impairment of or a waiver of other rights or remedies. No single or partial exercise of a right or remedy provided by this Deed or by law prevents further exercise of the right or remedy or the exercise of another right or remedy.

A person who is not a party to this Deed has no right under the Contracts (Rights of Third Parties) Act 1999 to enforce any term of this Deed, but this does not affect any right or remedy of a third party which exists or is available apart from the Contracts (Rights of Third Parties) Act 1999.

This Deed (including a dispute relating to its existence, validity or termination) and any non‑contractual obligations or other matters arising out of or in connection with it are governed by English law.

The courts of England have exclusive jurisdiction to settle any dispute arising from or connected with this Deed (including a dispute regarding the existence, validity or termination of this Deed or relating to any non‑contractual or other obligation arising out of or in connection with this Deed) or the consequences of its nullity.

It is not a U.S. person (as such term is defined in Rule 902(k) of Regulation S) (a "U.S. Person") and is not acquiring the Interests or the Shares for the account or benefit of any U.S. Person.

It was located outside the United States of America, its territories and possessions, any State of the United States and the District of Columbia (the "United States") at the time any offer to buy the Interests or the Shares was made to it and at the time that any buy order was originated by it.

The Interests and the Shares were not offered to it by means of any directed selling efforts (as such term is defined in Rule 902(c) of Regulation S).

The Shares have not been registered under the Securities Act and may be offered and sold only in accordance with Regulation S, pursuant to registration under the Securities Act, or pursuant to an available exemption from registration.

Hedging transactions involving the Shares may not be conducted unless in compliance with the Securities Act.

The Shares are "restricted securities" within the meeting of Rule 144(a)(3) under the Securities Act and no representation can be made as to the availability of the exemption provided by Rule 144 under the Securities Act for resales of the Shares.

The Company may refuse to register any transfer of the Shares not made in accordance with the provisions of Regulation S, pursuant to registration under the Securities Act or pursuant to an available exemption from registration.

Any offer or sale by it of the Shares, if made prior to the expiration of the six (6) month distribution compliance period (calculated in accordance with Rule 902(f) of Regulation S), will be made pursuant to the following conditions:

The purchaser certifies that it is not a U.S. Person and is not acquiring the Shares for the account or benefit of any U.S. Person or is a U.S. Person who purchased the securities in a transaction that did not require registration under the Securities Act; and

The purchaser agrees to resell such Shares only in accordance with the provisions of Regulation S, pursuant to registration under the Securities Act, or pursuant to an available exemption from registration, and agrees not to engage in hedging transactions with regard to such Shares unless in compliance with the Securities Act.

Upon the original issuance of the Shares, and until no longer required under the Securities Act or applicable state securities laws, the certificates representing the Shares will bear the following legend:

to be acquired by the Employee after [dd/mm/yyyy] under the terms of [insert scheme/plan name]

S431(2) ITEPA: The following specified restriction : [details of specified restriction]