Proposed Tender Offer and Notice of GM

Helios Underwriting Plc

29 September 2026

29 September 2026

NOT FOR RELEASE, PUBLICATION OR DISTRIBUTION IN WHOLE OR IN PART IN, INTO OR FROM ANY JURISDICTION WHERE TO DO SO WOULD CONSTITUTE A VIOLATION OF THE RELEVANT LAWS OF SUCH JURISDICTION.

THIS ANNOUNCEMENT IS NOT A PROSPECTUS OR A PROSPECTUS EXEMPT DOCUMENT AND SHAREHOLDERS SHOULD NOT MAKE ANY DECISION IN RELATION TO THE TENDER OFFER EXCEPT ON THE BASIS OF THE INFORMATION TO BE CONTAINED IN THE CIRCULAR WHICH IS PROPOSED TO BE PUBLISHED IN DUE COURSE.

HELIOS UNDERWRITING PLC

(“Helios” or the “Company”)

Proposed return of up to £7,199,998 to Shareholders by way of a tender offer at 269p per Ordinary Share

Notice of General Meeting

Helios Underwriting plc, the only publicly traded company offering instant access to a diverse portfolio of syndicates at Lloyd's of London,announces its intention to return up to £7,199,998 in cash at 269 pence per Ordinary Share (the "Tender Price") to Shareholders by way of a tender offer (the "Tender Offer").

The Tender Price is based on the latest NAV for the Company and represents a premium of approximately 17.7 per cent. to the middle market closing price of an Ordinary Share on 28 September 2026.

Following strong results over recent years, and good underwriting conditions in the Lloyd’s market, and as anticipated in our recent results announcement for 2024 and 2025, the Board has decided to make a distribution of up to £7,199,998 to Shareholders by way of a tender offer based on the latest NAV per Ordinary Share.

We have used Q2 2026 NAV for the purposes of the Tender Offer as published in our Interim Report and Financial Statements for the six months ended 30 June 2026 on 29 September 2026.

Accordingly, the Board has resolved to make a distribution of up to £7,199,998 to Shareholders by way of the Tender Offer, subject to the passing of the Tender Offer Resolution.

The Board considers that the Tender Offer is the most suitable way of returning excess capital to Shareholders in a quick and efficient manner, taking into account the relative costs, complexity and timeframes of other possible methods, as well as the likely tax treatment for and equality of treatment of Shareholders.

The Circular, which is expected to be posted to shareholders and be available on the Company's website later today, sets out the terms of the Tender Offer and incorporates a notice of General Meeting to be held at 9.30 a.m. on 26 October 2026 at the offices of Helios Underwriting PLC, 1st Floor, 33 Cornhill, London, United Kingdom EC3V 3ND, at which Shareholders will be asked to consider and, if thought fit, to approve the Tender Offer Resolution. A Tender Form for use by Shareholders who hold their Ordinary Shares in certificated form in connection with the Tender Offer will also be despatched with the Circular. Shareholders who hold their Ordinary Shares electronically through CREST and wish to tender such Ordinary Shares, must make their tender electronically through CREST.

For further information, please contact:

Helios Underwriting plc
Louis Tucker - Chief Executive Officer	+44 (0)20 3965 6441
Adhiraj Maitra - Director of Finance and Operations	+44 (0)20 3743 2114
Peel Hunt (Nomad, Broker and Financial Adviser)
Dan Webster / Andrew Buchanan / Martin Frowde	+44 (0)20 7418 8900
Singer Capital Markets (Joint Broker)
Charles Leigh-Pemberton / Russell Cook / James Todd	+44 (0)20 7496 3000
FTI Consulting
Ed Berry	+44 (0)7703 330 199
Christian Harte	+44 (0)7974 288 763

About Helios

Helios provides a limited liability direct investment into the Lloyd's insurance market and is quoted on the London Stock Exchange's AIM market (ticker: HUW). Helios trades within the Lloyd's insurance market. The portfolio provides a broad spread of business primarily participating in the US and other international wholesale and reinsurance markets. For further information please visitwww.huwplc.com

Notice in relation to overseas persons:

The release, publication or distribution of this announcement in or into jurisdictions other than the UK may be restricted by law and therefore any person who is subject to the laws of any jurisdiction other than the UK should inform themselves about and observe any of those restrictions. Any failure to comply with any of those restrictions might constitute a violation of the relevant laws or regulations of such jurisdiction.

Forward-looking statements:

This announcement includes "forward-looking statements" which include all statements other than statements of historical fact, including, without limitation, those regarding the Company and its existing subsidiaries and subsidiary undertakings’ (the “Group”) financial position, business strategy, plans and objectives of management for future operations, or any statements preceded by, followed by or that include the words "targets", "believes", "expects", "aims", "intends", "will", "may", "anticipates", "would, "could" or similar expressions or negatives thereof. Such forward-looking statements involve known and unknown risks, uncertainties and other important factors beyond the Group's control that could cause the actual results, performance or achievements of the Group to be materially different from the future results, performance or achievements expressed or implied by such forward-looking statements. Such forward-looking statements are based on numerous assumptions regarding the Group's present and future business strategies and the environment in which the Group will operate in the future. These forward-looking statements speak only as at the date of this announcement. Whilst the Directors consider these statements to be reasonable based upon information currently available, they may prove to be incorrect. However, the Company expressly disclaims any obligation or undertaking to disseminate any updates or revisions to any forward-looking statements contained herein to reflect any change in the Group's expectations with regard thereto or any change in events, conditions or circumstances on which any such statements are based unless required to do so by applicable law.

No profit forecast or estimates:

Unless otherwise stated, no statement in this announcement is intended as a profit forecast or estimate for any period and no statement in this announcement should be interpreted to mean that earnings, earnings per share or income, cash flow from operations or free cash flow for the Group, for the current or future financial years would necessarily match or exceed the historical published earnings, earnings per share or income, cash flow from operations or free cash flow from the Group.

Peel Hunt LLP ("Peel Hunt"), which is authorised and regulated in the United Kingdom by the Financial Conduct Authority ("FCA"), is acting exclusively for the Company and for no one else in connection with the Tender Offer, including any recipient of this announcement and Peel Hunt, its affiliates and its and their respective directors, officers, employees and agents and are not and will not be responsible to anyone other than the Company for providing the protections afforded to clients of Peel Hunt or for affording advice in relation to the Tender Offer, the contents of this announcement or any other matter referred to in this announcement.

Peel Hunt is acting as nominated adviser to the Company in connection with the arrangements described in this announcement. The responsibility of Peel Hunt, as the Company’s nominated adviser, under the AIM Rules for Nominated Advisers is owed solely to the London Stock Exchange and is not owed to the Company or the Directors or any other person. Persons receiving this announcement should note that Peel Hunt will not be responsible to anyone other than the Company for providing the protections afforded to customers of Peel Hunt or for advising any other person on the arrangements described in this announcement. No representation or warranty, expressed or implied, is made by Peel Hunt as to any of the contents of this announcement and Peel Hunt has not authorised the contents of, or any part of, this announcement and no liability whatsoever is accepted by Peel Hunt for the accuracy of any information or opinions contained in this announcement or for the omission of any other information.

Notice for US Shareholders

The Tender Offer relates to securities in a non-US company that is registered in the UK and is subject to the disclosure requirements, rules and practices applicable to companies listed in the UK, which differ from those of the US in certain material respects. The Circular has been prepared in accordance with UK style and practice for the purpose of complying with English law and the AIM Rules, and US Shareholders should read the entire Circular. The financial information relating to the Company, which is available for review on the Company’s website, has not been prepared in accordance with generally accepted accounting principles in the US and thus may not be comparable to financial information relating to US companies.

The Tender Offer is not subject to the disclosure and other procedural requirements of Rule 13e-4 or Regulation 14D under the US Securities Exchange Act of 1934, as amended (the “Exchange Act”). The Tender Offer will be made in the US in accordance with the requirements of Regulation 14E under the Exchange Act to the extent applicable. Certain provisions of Regulation 14E under the Exchange Act are not applicable to the Tender Offer by virtue of the exemption provided under rule 14d-1(d) under the Exchange Act for a Tier II tender offer. Peel Hunt Inc., an affiliate of Peel Hunt, will act as US dealer manager with respect to the Tender Offer in the United States to the extent required. US Shareholders should note that the Ordinary Shares are not listed on a US securities exchange and the Company is not subject to the periodic reporting requirements of the Exchange Act and is not required to, and does not, file any reports with the US Securities and Exchange Commission thereunder. It may be difficult for Shareholders in the United States to enforce certain rights and claims arising in connection with the Tender Offer under US federal securities laws since the Company is located outside the United States and most of its officers and directors may reside outside the United States. It may not be possible to sue a non-US company or its officers or directors in a non-US court for violations of US securities laws. It also may not be possible to compel a non-US company or its affiliates to subject themselves to a US court’s judgement.

To the extent permitted by applicable law and in accordance with normal UK practice, the Company, Peel Hunt, or any of their respective affiliates may make certain purchases of, or arrangements to purchase, Ordinary Shares outside the United States before or during the period in which the Tender Offer remains open for acceptance, including sales and purchases of Ordinary Shares effected by Peel Hunt acting as market maker in the Ordinary Shares. These purchases, or other arrangements, may occur either in the open market at prevailing prices or in private transactions at negotiated prices. In order to be excepted from the requirements of Rule 14e-5 under the Exchange Act by virtue of Rule 14e-5(b)(12) thereunder, such purchases, or arrangements to purchase, must comply with the applicable English law and regulation and the relevant provisions of the Exchange Act. Any information about such purchases will be disclosed as required in the UK and the United States and, if required, will be reported via a Regulatory Information Service and will be available on the London Stock Exchange website at http://www.londonstockexchange.com.

The receipt of cash pursuant to the Tender Offer by a Shareholder who is a US person may be a taxable transaction for US federal income tax purposes. Each such Shareholder should consult and seek individual advice from an appropriate professional adviser.

While the Tender Offer is being made available to Shareholders in the US, the right to tender Ordinary Shares is not being made available in any jurisdiction in the US in which the making of the Tender Offer or the right to tender such Ordinary Shares would not be in compliance with the laws of such jurisdiction.

The Circular has not been approved, disapproved or otherwise recommended by the US Securities and Exchange Commission or any US state securities commission and such authorities have not confirmed the accuracy or determined the adequacy of the Circular. Any representation to the contrary is a criminal offence in the US.

EXPECTED TIMETABLE

Posting of the Circular	29 September 2026
Tender Offer opens	29 September 2026
Latest time and date for receipt of CREST Proxy Instructions for the General Meeting	9.30 a.m. on 22 October 2026
Latest time and date for receipt of Forms of Proxy for the General Meeting	9.30 a.m. on 22 October 2026
General Meeting	9.30 a.m. on 26 October 2026
Closing Date - latest time and date for receipt of Tender Forms or for settlement of TTE Instructions in respect of the Tender Offer	11.00 a.m. on 28 October 2026
Record Date for the Tender Offer	6.00 p.m. on 28 October 2026
Result of Tender Offer announced	30 October 2026
CREST accounts settled in respect of unsold tendered Ordinary Shares held in uncertificated form, payments through CREST and cheques dispatched in respect of Ordinary Shares held in certificated and uncertificated form successfully tendered, and balancing certificates dispatched in respect of unsold tendered Ordinary Shares held in certificated form	on or around 3 November 2026

PROPOSED PURCHASE OF UP TO 2,676,579 ORDINARY SHARES REPRESENTING APPROXIMATELY3.5PER CENT. OF THE COMPANY'S ISSUED SHARE CAPITAL AT A PRICE OF 269 PENCE PER ORDINARY SHARE AND NOTICE OF GENERAL MEETING (to authorise the Tender Offer)

1.Introduction

The Company intends to undertake a return of capital of up to £7,199,998 through a tender offer by Peel Hunt to Qualifying Shareholders and subsequent repurchase by the Company from Peel Hunt of the Ordinary Shares successfully tendered (the "Tender Offer").

The Tender Offer will be conducted at a fixed price of 269 pence per Ordinary Share (the "Tender Price"), based on the latest NAV for the Company and which represents a premium of approximately 17.7 per cent. to the middle market closing price of an Ordinary Share on 28 September 2026 (being the "Latest Practicable Date")and will be made subject to the passing of the Tender Offer Resolution by Shareholders as set out in the Notice of General Meeting in Part 7 of the Circular.

If the maximum number of Ordinary Shares under the Tender Offer is acquired, this would result in the purchase of approximately 3.5 per cent. of the Company's current issued share capital. The Company is seeking authority to buy back up to 2,676,579 Ordinary Shares pursuant to the Tender Offer Resolution to be put before Shareholders at the General Meeting.

The purpose of the Circular is to explain the terms and conditions of the Tender Offer and subsequent repurchase of Ordinary Shares and to explain how Qualifying Shareholders may tender Ordinary Shares, should they wish to do so, and why the Board unanimously recommends that you vote in favour of the Tender Offer Resolution to approve the Tender Offer to be proposed at the General Meeting, to be held at 9.30 a.m. on 26 October 2026, notice of which is set out in Part 7 of the Circular.

This letter is not a recommendation to Shareholders to sell or tender their Ordinary Shares. Shareholders are not obliged to tender any Ordinary Shares and Shareholders who wish to retain all of their investment in the Company should not return a Tender Form or submit a TTE Instruction.

2.Background to and reasons for the Tender Offer

Following strong results over recent years, and good underwriting conditions in the Lloyd’s market, and as anticipated in our recent results announcement for 2026, the Board has decided to make a distribution of up to £7,199,998 to Shareholders by way of a tender offer based on the latest NAV per Ordinary Share.

We have used Q2 2026 NAV for the purposes of the Tender Offer as published in our “Interim Report and Financial Statements for the six months ended 30 June 2026” on 29 September 2026.

Accordingly, the Board has resolved to make a distribution of up to £7,199,998 to Shareholders by way of the Tender Offer, subject to the passing of the Tender Offer Resolution.

The Board considers that the Tender Offer is the most suitable way of returning excess capital to Shareholders in a quick and efficient manner, taking into account the relative costs, complexity and timeframes of other possible methods, as well as the likely tax treatment for and equality of treatment of Shareholders.

The purpose of the Circular is to provide you with the terms and conditions relating to the Tender Offer and explain how you may tender some or all of your Ordinary Shares in the Tender Offer, should you wish to do so.

3.The Tender Offer

Overview

The key points of the Tender Offer are as follows:

the Tender Offer will be restricted to a maximum number of 2,676,579 Ordinary Shares, representing approximately 3.5 per cent. of the Ordinary Shares in issue on the Record Date;

each Qualifying Shareholder will be entitled to tender up to 3.5 per cent. of their holding (rounded down to the nearest whole number of Ordinary Shares), held at the Record Date, with such tenders being satisfied in full ("Basic Entitlement");

Qualifying Shareholders are permitted to tender Ordinary Shares in excess of their Basic Entitlement ("Excess Tenders"). To the extent that any Qualifying Shareholder does not tender its Basic Entitlement in full, the balance of that Basic Entitlement not taken up (in aggregate across all Qualifying Shareholders ("Unallocated Entitlement")) will be made available to satisfy Excess Tenders. Where the aggregate of Excess Tenders exceeds the Unallocated Entitlement, Excess Tenders will be satisfied on a pro rata basis in proportion to the number of Ordinary Shares in respect of which applications are made in excess of the Basic Entitlement rounded down to the nearest whole number of Ordinary Shares. Peel Hunt (in consultation with the Company) may, in its discretion, adjust such scaling down where considered necessary or expedient; and

• the Tender Price will be fixed at 269 pence per Ordinary Share which represents a premium of approximately 17.7 per cent. to the middle market closing price of an Ordinary Share on 28 September 2026, the Latest Practicable Date before the publication of the Circular.

Structure of the Tender Offer

The Tender Offer will be implemented on the basis of Peel Hunt acquiring, as principal, the successfully tendered Ordinary Shares at the Tender Price. The Company will purchase such Ordinary Shares from Peel Hunt at the same price under the Repurchase Agreement. The Company will cancel the Ordinary Shares purchased by it under the Repurchase Agreement.

Up to a maximum of 2,676,579 Ordinary Shares will be purchased under the Tender Offer, representing approximately 3.5 per cent. of the Company's current issued share capital, for a maximum aggregate consideration of £7,199,998. The Tender Offer is conditional on, among other things, the passing of the Tender Offer Resolution at the General Meeting and the conditions set out in paragraph 2.1 of Part 3 of the Circular.

Qualifying Shareholders can decide whether they want to tender all, some or none of their Ordinary Shares in the Tender Offer. In addition, Qualifying Shareholders may submit Excess Tenders, which Peel Hunt may purchase depending on the number of Ordinary Shares tendered by other Shareholders.

Excess Tenders will only be accepted to the extent that other Qualifying Shareholders tender less than their Basic Entitlement or do not tender any of their Ordinary Shares. Excess Tenders will be satisfied on a pro rata basis in proportion to the number of Ordinary Shares in respect of which applications are made in excess of the Basic Entitlement rounded down to the nearest whole number of Ordinary Shares. Peel Hunt (in consultation with the Company) may, in its discretion, adjust such scaling down where considered necessary or expedient. All Ordinary Shares validly tendered by any Qualifying Shareholder up to their Basic Entitlement will be accepted in full.

The Tender Offer is being made available to all Qualifying Shareholders on the Register on the Record Date. The Tender Offer will close at 11.00 a.m. on 28 October 2026 and tenders received after that time will not be accepted (unless the Tender Offer is extended).

The Tender Price

A Tender Price of 269 pence per Ordinary Share will be applied to all Ordinary Shares purchased by Peel Hunt pursuant to the Tender Offer. The Tender Price will allow Peel Hunt to purchase the maximum number of Ordinary Shares for a total cost not exceeding £7,199,998 or, if the aggregate price of all Ordinary Shares validly tendered by Qualifying Shareholders is less than £7,199,998, all of the Ordinary Shares validly tendered pursuant to the Tender Offer.

Number of Ordinary Shares to be purchased

Under the Tender Offer, each Qualifying Shareholder is entitled to tender up to 3.5 per cent. of their holding (rounded down to the nearest whole number of Ordinary Shares) held at the Record Date to be purchased by Peel Hunt at the Tender Price (being their Basic Entitlement). Each Qualifying Shareholder's Basic Entitlement will be calculated by the Receiving Agent as at the Record Date by reference to the Qualifying Shareholder's holding of Ordinary Shares as at that date.

Provided that the conditions in paragraph 2.1 of Part 3 of the Circular are met, if the aggregate value at the Tender Price of all validly tendered Ordinary Shares is less than £7,199,998, then all Ordinary Shares validly tendered up to each Qualifying Shareholder's Basic Entitlement will be purchased at the Tender Price.

For the avoidance of doubt, the number of Ordinary Shares to be purchased in the Tender Offer will not, in any event, exceed 2,676,579 Ordinary Shares. Once lodged (in the case of a Tender Form for certificated Shareholders only) or settled (in the case of a TTE Instruction for CREST Shareholders only) such tender shall be irrevocable. Ordinary Shares will be purchased pursuant to the Tender Offer on or around 3 November 2026. Successfully tendered Ordinary Shares will be purchased free of commission and dealing charges. Any Ordinary Shares repurchased by the Company from Peel Hunt following the purchase by Peel Hunt will be cancelled and the number of Ordinary Shares in issue carrying voting rights reduced accordingly. Any rights of Shareholders who do not tender their Ordinary Shares will be unaffected. Subject to any applicable rules and regulations, the Company reserves the right at any time prior to the announcement of the results of the Tender Offer, and with the prior consent of Peel Hunt, to extend the period during which the Tender Offer is open, based on market conditions and/or other factors.

Shareholders should note that, once tendered, Ordinary Shares may not be sold, transferred, charged or otherwise disposed of other than in accordance with the Tender Offer.

Shareholders who are in any doubt as to the contents of the Circular or as to the action to be taken should immediately consult their stockbroker, bank manager, solicitor, accountant or other independent financial adviser authorised under FSMA.

Basic Entitlement

Ordinary Shares tendered under the Tender Offer in respect of 3.5 per cent. of their holding (rounded down to the nearest whole number of Ordinary Shares) held at the Record Date will be accepted in full at the Tender Price and will not be scaled down, provided that such Ordinary Shares are validly tendered. This percentage is known as the Basic Entitlement. Provided that the conditions in paragraph 2.1 of Part 3 of the Circular are met, if the aggregate value at the Tender Price of all validly tendered Ordinary Shares is less than £7,199,998, then all Ordinary Shares validly tendered up to each Qualifying Shareholder's Basic Entitlement will be purchased at the Tender Price.

Tenders of Ordinary Shares in excess of the Basic Entitlement

If the total number of Ordinary Shares validly tendered by all Qualifying Shareholders equates to a number greater than 2,676,579 Ordinary Shares, tenders will be accepted in the order set out below:

-all Ordinary Shares validly tendered by any Qualifying Shareholder up to their Basic Entitlement will be accepted in full;

-all or any part of a holding of Ordinary Shares may be tendered up to a Qualifying Shareholder’s Basic Entitlement;

-Qualifying Shareholders may also tender Ordinary Shares in excess of their Basic Entitlement ("Excess Tenders"). To the extent that any Qualifying Shareholder does not tender its Basic Entitlement in full, the balance of that Basic Entitlement not taken up (in aggregate across all Qualifying Shareholders, the "Unallocated Entitlement") shall be made available to satisfy Excess Tenders; and

-where the aggregate of Excess Tenders exceeds the Unallocated Entitlement, Ordinary Shares validly tendered by Qualifying Shareholders in excess of their Basic Entitlement will be satisfied on a pro rata basis in proportion to the number of Ordinary Shares in respect of which applications are made in excess of the Basic Entitlement rounded down to the nearest whole number of Ordinary Shares, provided that Peel Hunt (in consultation with the Company) may, in its discretion, adjust such scaling down to the extent considered necessary or expedient.

The number of Ordinary Shares to be purchased in the Tender Offer will not, in any event, exceed 2,676,579 Ordinary Shares. Ordinary Shares successfully tendered will be sold to Peel Hunt fully paid and free from all liens, charges, equitable interests and encumbrances and with all rights attaching to the same.

Circumstances in which the Tender Offer may not proceed

There is no guarantee that the Tender Offer will take place. The Tender Offer is conditional on the passing of the Tender Offer Resolution set out in the Notice of General Meeting. The Tender Offer is also conditional on the other matters specified in paragraph 2.1 of Part 3 (Details of the Tender Offer) of the Circular, including:

1. the Tender Offer not having been terminated in accordance with its terms and the Company having confirmed to Peel Hunt that it will not exercise its right to require Peel Hunt not to proceed with the Tender Offer; and

1. Peel Hunt being satisfied at all times up to immediately prior to the Unconditional Date that the Company has complied with its obligations and the conditions set out under the Repurchase Agreement, and the Company is not in breach of any of the representations and warranties given by it under the Repurchase Agreement.

The Board has reserved the right, at any time prior to the Tender Offer becoming unconditional, to require Peel Hunt not to proceed with the Tender Offer if the Board concludes that the implementation of the Tender Offer is no longer in the best interests of the Company and/or Shareholders as a whole. The Board has also reserved the right, at any time prior to the announcement of the results of the Tender Offer, with the prior consent of Peel Hunt, to extend the period during which the Tender Offer is open, based on market conditions and/or other factors, subject to compliance with applicable legal and regulatory requirements.

Settlement

Subject to the Tender Offer becoming unconditional and the acquisition of the Ordinary Shares pursuant to the Tender Offer by Peel Hunt, payment of the Tender Price due to Qualifying Shareholders whose tenders under the Tender Offer have been accepted will be made (a) by a Sterling cheque (for certificated Shareholders only), expected to be dispatched on or around 3 November 2026; or (b) by a CREST payment (for CREST Shareholders only), expected to be made on or around 3 November 2026, as appropriate.

If any tendered Ordinary Shares are not purchased because of an invalid tender, the termination of the Tender Offer or otherwise, relevant share certificate(s) and/or other documents of title, if any, will be returned or sent as promptly as practicable, without expense to, but at the risk of, the relevant tendering Qualifying Shareholder, or in the case of Ordinary Shares held in uncertificated form (that is, in CREST), the Receiving Agent will provide instructions to Euroclear to transfer all Ordinary Shares held in escrow balances by TFE Instruction to the original available balances from which those Ordinary Shares came.

1. Authority to make market purchases of own shares

The Notice of General Meeting in Part 7 of the Circular sets out the Tender Offer Resolution to authorise the Company to buy back up to a maximum of 2,676,579 Ordinary Shares, representing approximately 3.5 per cent. of the issued share capital of the Company, pursuant to (and solely in relation to) the Tender Offer.

The Tender Offer Resolution is a special resolution. In order to be passed, the Tender Offer Resolution must be passed on a poll by at least 75 per cent. of the votes validly cast by Shareholders attending the General Meeting in person or by proxy.

1. Repurchase Agreement

Under the Repurchase Agreement, the Company and Peel Hunt have agreed that, subject to, amongst other things, the sum of up to £7,199,998 (equal to the Tender Price multiplied by the maximum number of Ordinary Shares that could be repurchased under the Tender Offer) being received by Peel Hunt (or its custodian) by no later than 5 p.m. on 28 October 2026 (or such later time and/or date as may be agreed by Peel Hunt and the Company) and the Tender Offer becoming unconditional in all respects and not lapsing or terminating in accordance with its terms, Peel Hunt shall, as principal, purchase, "on exchange", at the Tender Price, Ordinary Shares successfully tendered to it, up to a maximum aggregate value, at the Tender Price, of £7,199,998.

The Company has agreed that, immediately following the purchase by Peel Hunt of all Ordinary Shares which it has agreed to purchase as principal under the terms of the Tender Offer, the Company will purchase from Peel Hunt all such Ordinary Shares at a price per Ordinary Share equal to the Tender Price. All transactions will be carried out on the London Stock Exchange.

The Repurchase Agreement contains certain customary warranties from Peel Hunt in favour of the Company concerning its authority to enter into the Repurchase Agreement and to make the purchase of Ordinary Shares pursuant thereto. The Repurchase Agreement also contains warranties and undertakings from the Company in favour of Peel Hunt and incorporates a customary indemnity in favour of Peel Hunt in respect of any liability which it may suffer in relation to the performance of its obligations under the Tender Offer.

1. Overseas Shareholders

The attention of Qualifying Shareholders who are citizens, residents or nationals of countries outside the UK wishing to participate in the Tender Offer is drawn to paragraph 6 (entitled "Overseas Shareholders") in Part 3 of the Circular. In addition, the attention of Shareholders who are resident in the United States is drawn to the Notice on page 3 of the Circular.

1. Taxation

Qualifying Shareholders should be aware that there may be tax considerations that they should take into account when deciding whether or not and/or the extent to which to participate in the Tender Offer. A summary of the taxation consequences of the Tender Offer for UK resident Shareholders is set out in Part 5 of the Circular. It should be noted that this tax summary is merely a guide to current tax law and practice in the UK. Shareholders are advised to consult their own professional advisers regarding their own tax position.

1. Notification of interests

Under chapter 5.1.2 of the Disclosure Guidance and Transparency Rules ("DTR"), certain Shareholders are required to notify the Company of the percentage of voting rights they hold as Shareholders or through their direct or indirect holding of financial instruments within the limits referred to in the DTR. Following any purchase by the Company of Ordinary Shares from Peel Hunt pursuant to the Repurchase Agreement, the percentage of voting rights held by a Shareholder may change. Such a change in the percentage of voting rights held by a Shareholder may give rise to an obligation on the Shareholder to notify the Company as soon as possible, but not later than two trading days, after becoming aware or being deemed to have become aware of such change. If Shareholders are in any doubt as to whether they should notify the Company or as to the form of that notification, they should consult their solicitor or other professional adviser.

1. Action to be taken
   General Meeting

Whether or not you intend to attend the General Meeting in person, you are encouraged to submit a proxy vote.

Shareholders can complete and return a Form of Proxy so that the instruction is received by Neville Registrars Limited by not later than 9.30 a.m. on 22 October 2026. CREST members can also appoint proxies by using the CREST electronic proxy appointment service and transmitting a CREST Proxy Instruction in accordance with the procedures set out in the CREST Manual so that it is received by Neville Registrars Limited (under CREST ID:7RA11) by not later than 9.30 a.m. on 22 October 2026. The time of receipt will be taken to be the time from which Neville Registrars Limited is able to retrieve the message by enquiry to CREST in the manner prescribed by CREST.

Tender Offer

Only Qualifying Shareholders whose names appeared on the Register on the Record Date are able to participate in the Tender Offer in respect of the Ordinary Shares held as at that date.

(a) Ordinary Shares held in certificated form

Qualifying Shareholders who hold Ordinary Shares in certificated form and who wish to participate in the Tender Offer should follow the instructions on the Tender Form provided to them and return it to the Receiving Agent to arrive by no later than 11.00 a.m. on 28 October 2026. Qualifying Shareholders who hold their Ordinary Shares in certificated form should also send their original valid share certificate(s) in respect of the Ordinary Shares tendered with their Tender Form.

(b) Ordinary Shares held in uncertificated form

Qualifying Shareholders who hold their Ordinary Shares in uncertificated form (that is, in CREST) and who wish to participate in the Tender Offer should tender electronically through CREST so that the TTE Instruction settles no later than 11.00 a.m. on 28 October 2026.

Further details of the procedures for tendering and settlement are set out in Part 3 of the Circular.

Shareholders who do not wish to participate in the Tender Offer should not complete the Tender Form and should not make or arrange for a TTE Instruction.

1. General Meeting and the Tender Offer Resolution

A general meeting of the Company will be held at Helios Underwriting PLC, 1st Floor, 33 Cornhill, London, United Kingdom EC3V 3ND at 9.30 a.m. on 26 October 2026 to consider the Tender Offer Resolution. Notice of the meeting is in Part 7 of the Circular.

The Tender Offer Resolution, which is a special resolution, seeks authority to make market purchases of Ordinary Shares in connection with the Tender Offer. The Tender Offer Resolution specifies the Tender Price and the maximum number of Ordinary Shares which may be acquired pursuant to this authority. The authority sought will expire 6 months following the passing of the Tender Offer Resolution. In order to be passed, the Tender Offer Resolution must be passed on a poll by at least 75 per cent. of the votes validly cast by Shareholders attending the General Meeting in person or by proxy.

1. General

Any repurchase of Ordinary Shares pursuant to the Repurchase Agreement will be financed solely from the Company's existing cash resources. No borrowings will be incurred by the Company in respect of any repurchase of Ordinary Shares pursuant to the Repurchase Agreement.

As at the Latest Practicable Date, the issued share capital of the Company carrying voting rights was 69,505,965 Ordinary Shares.

Peel Hunt has given and has not withdrawn its written consent to the issue of the Circular with the inclusion of its name and the references to it in the form, and context in which it appears.

If you choose not to tender your Ordinary Shares under the Tender Offer, your holding will be unaffected, save for the fact that, assuming the successful completion of the Tender Offer and subsequent repurchase of Ordinary Shares by the Company, you will end up holding a greater percentage of the issued share capital of the Company than you did before the Tender Offer as there will be fewer Ordinary Shares in issue after completion of the Tender Offer and subsequent repurchase of Ordinary Shares.

1. Related party transaction

The intention of Nigel Hanbury, Tom Libassi and Andrew Christie and/or their associated parties to participate in the Tender Offer is deemed to constitute a related party transaction for the purposes of AIM Rule 13. The independent directors for these purposes (being John Chambers, Louis Tucker, Adhiraj Maitra, Katie Wade and Joanna Parsons), having consulted with the Company’s nominated adviser Peel Hunt, confirm that they consider that the terms of the transaction are fair and reasonable insofar as Shareholders are concerned.

1. Issued Ordinary Shares following the Tender Offer

Assuming that the maximum number of Ordinary Shares under the Tender Offer are bought back by the Company and cancelled, the Company's issued share capital carrying voting rights will be reduced by 2,676,579 Ordinary Shares to 66,829,386 Ordinary Shares. An announcement setting out the Company's new issued share capital for the purposes of making DTR 5.1.2 notifications will be made following any purchase by the Company of Ordinary Shares from Peel Hunt in relation to the Tender Offer.

1. Further information

Your attention is drawn to the information contained in the Circular, including, in particular, the terms and conditions of the Tender Offer in Part 3 of the Circular.

1. Recommendation

The Board considers the Tender Offer Resolution to be in the best interests of Shareholders as a whole. Accordingly, the Board recommends that Shareholders vote in favour of the Tender Offer Resolution to be proposed at the General Meeting, as the Directors intend to do for their respective individual beneficial holdings of, in aggregate, 21,439,046 Ordinary Shares, representing approximately 28.2 per cent. of the Company's issued share capital as at the Latest Practicable Date.

The Directors are making no recommendation to Qualifying Shareholders in relation to participation in the Tender Offer itself. Whether or not Qualifying Shareholders decide to tender all, or any, of their Ordinary Shares will depend on, among other things, their view of the Company’s prospects and their own individual circumstances, including their own financial and tax position. Shareholders are required to take their own decision and are recommended to consult with their duly authorised independent financial or professional adviser.

If you are in any doubt as to the action you should take, you are recommended to seek your own independent advice. You are advised to read all of the information contained in the Circular before deciding on the course of action you will take in respect of the General Meeting and the Tender Offer. The results of the General Meeting will be announced through a Regulatory Information Service and the Company’s website as soon as possible once known. It is expected that this will be announced on or around 30 October 2026.

DEFINITIONS

The following definitions apply throughout this announcement unless the context otherwise requires:

“Agent”	any director or officer of Peel Hunt to be appointed as a Qualifying Shareholder's attorney and/or agent, following the tender of Ordinary Shares by way of a Tender Form, in accordance with sub-paragraph 4(c) of Part 3 of the Circular
“AIM”	the AIM Market operated by the London Stock Exchange
“AIM Rules”	the AIM Rules for Companies published by the London Stock Exchange from time to time
“Annual Exempt Amount”	amount by which gains are relieved or reduced by the annual exemption
“Attorney”	any director or officer of Peel Hunt to be appointed as a Qualifying Shareholder's attorney and/or agent, following the tender of Ordinary Shares by way of Electronic Tender, in accordance with sub-paragraph 5(c) of Part 3 of the Circular
“Basic Entitlement”	in the case of each Shareholder, the entitlement to tender their Ordinary Shares representing up to 3.5 per cent. of the Ordinary Shares registered in the Register in such person's name at the Record Date rounded down to the nearest whole number of Ordinary Shares (or to nil as the case may be)
“Board”	the board of Directors, including any duly constituted committee thereof
“Business Day”	any day other than a Saturday, Sunday or public holiday in England and Wales on which clearing banks in London and St Helier are open for general banking business
“certificated” or “in certificated form”	recorded on the Register as being held in certificated form (that is, not in CREST)
“Closing Date”	closing date for the Tender Offer, being 11.00 a.m. on 28 October 2026
“Company”	Helios Underwriting PLC
“Company’s Registrar”	Neville Registrars Limited of Neville House, Steelpark Road, Halesowen B62 8HD
“Conditions”	the conditions set out in paragraph 2.1 of Part 3 of the Circular, which the Tender Offer is conditional on
“CREST”	the facilities and procedures for the time being of the relevant system of which Euroclear has been approved as operator pursuant to the CREST Regulations
“CREST Application Host”	the system that is operated to receive, manage and control the processing of the messages by the CREST system
“CREST Manual”	the compendium of documents entitled CREST Manual issued by Euroclear from time to time and comprising the CREST Reference Manual, the CREST Central Counterparty Service Manual, the CREST International Manual, the CREST Rules, CCSS Operations Manual and the CREST Glossary of Terms
“CREST member”	a person who has been admitted by Euroclear as a system-member (as defined in the CREST Regulations)
“CREST participant”	person who is, in relation to CREST, a system participant (as defined in the CREST Regulations)
CREST Proxy Instruction	a proxy appointment or instruction made via CREST authenticated in accordance with Euroclear’s specifications and containing the information set out in the CREST Manual CREST Regulations the Uncertificated Securities Regulations 2001 (SI 2001 No. 3755), as amended from time to time
“CREST Regulations”	the Uncertificated Securities Regulations 2001 (SI 2001 No. 3755)
“CREST Sponsor”	A CREST participant admitted to CREST as a CREST sponsor, being a sponsoring system participant (as defined in the CREST Regulations)
“CREST sponsored member”	a CREST member admitted to CREST as a sponsored member
“Directors”	the directors of the Company, whose names appear on page 7 of the Circular
“DTR”	Disclosure Guidance and Transparency Rules
“Electronic Tenders”	in case of each Shareholder (other than Restricted Shareholders) holding uncertificated Ordinary Shares, the input and settlement of a TTE Instruction for the transfer of Ordinary Shares to the account of Neville Registrars Limited, in its capacity as escrow agent, with member account ID 7RA11
“Euroclear”	Euroclear UK & International Limited, the operator of CREST
“Excess Tenders”	in the case of each Shareholder (other than Restricted Shareholders), a tender of Ordinary Shares in excess of their Basic Entitlement
“Exchange Act”	The U.S. Securities Exchange Act of 1934
“FCA”	Financial Conduct Authority
“FSMA”	the Financial Services and Markets Act 2000, as amended from time to time
“Form of Proxy”	the form of proxy accompanying the Circular relating to the General Meeting
“General Meeting”	the general meeting of the Company convened for 9.30 a.m. on 26 October 2026 in accordance with the notice set out in Part 7 of the Circular
“Group”	the Company and/or any or all of its existing subsidiaries and subsidiary undertakings
“Latest Practicable Date”	28 September 2026
“London Stock Exchange”	London Stock Exchange plc
“member account ID”	the identification code or number attached to any member account in CREST
“Ordinary Shares”	ordinary shares of 10p each in the capital of the Company
“Overseas Shareholders”	a Shareholder who is resident in, or a national or citizen of, a jurisdiction outside the United Kingdom
“NAV”	the assessed net asset value of the Company, being the last reported NAV as at Q2 2026 adjusted for the dividend payment and costs associated with the Tender Offer
“participant ID”	the identification code or membership number used in CREST to identify a particular CREST member or other CREST participant
“Peel Hunt”	Peel Hunt LLP of 7th Floor 100 Liverpool Street, London, England, EC2M 2AT
“Qualifying Shareholders”	Shareholders on the Register at the Record Date other than those who are Restricted Shareholders
“Receiving Agent”	Neville Registrars Limited of Neville House, Steelpark Road, Halesowen B62 8HD
“Record Date”	the record date for the Tender Offer, being 6.00 p.m. on 28 October 2026
“Register”	the register of Shareholders
“Regulatory Information Service”	regulatory information service approved by the FCA and on the list of regulatory information services maintained by the FCA
“Repurchase Agreement”	the agreement dated 29 September 2026 between the Company and Peel Hunt whereby the Company has agreed to purchase, and Peel Hunt has agreed to sell to the Company, as an on-market purchase and at a price per Ordinary Share equal to the Tender Price, all of the Ordinary Shares purchased by Peel Hunt pursuant to the Tender Offer as summarised in paragraph 5 of Part 1 of the Circular
“Restricted Jurisdiction”	any of the following jurisdictions: Australia; Canada; Japan; New Zealand, the Republic of South Africa or in any other jurisdiction where participation in the Tender Offer will constitute a violation of the laws of that jurisdiction
“Restricted Shareholder”	a Shareholder who is a resident in, or a citizen or national of, a Restricted Jurisdiction or any other jurisdiction where the mailing of the Circular or the Tender Form in, into or from such jurisdiction would constitute a violation of the laws of such jurisdiction
“Shareholders”	holders of Ordinary Shares
“Tender Form”	the tender form issued by the Company for use by Shareholders in connection with the Tender Offer
“Tender Offer”	the invitation by Peel Hunt to Shareholders (other than Restricted Shareholders) to tender up to 2,676,579 Ordinary Shares in aggregate, representing approximately 3.5 per cent. of the Ordinary Shares in issue on the Record Date, for purchase on the terms and subject to the conditions set out in the Circular and, where applicable, the Tender Form
“Tender Offer Resolution”	the special resolution to be proposed at the General Meeting in connection with the Tender Offer
“Tender Price”	the fixed price of 269 pence per Ordinary Share at which Ordinary Shares will be purchased pursuant to the Tender Offer
“TFE Instruction”	a transfer from escrow instruction (as defined by the CREST Manual)
“TTE Instruction”	a transfer to escrow instruction (as defined by the CREST Manual)
“Unallocated Entitlement”	the aggregate balance of Basic Entitlement not taken up by Qualifying Shareholders as part of the Tender Offer
“Uncertificated Securities Regulations 2001”	The Uncertificated Securities Regulations 2001
“uncertificated form” or “in uncertificated form”	recorded in the Register as being held in uncertificated form in CREST and title to which may be transferred by means of CREST
“Unconditional Date”	the date on and time at which the Tender Offer becomes unconditional
“United Kingdom” or “UK”	the United Kingdom of Great Britain and Northern Ireland
“United States” or “US”	the United States of America, its territories and possessions, any state of the United States and the District of Columbia
Note: All references in this announcement to "£", "pounds sterling", "sterling" and "pence" (including the abbreviation "p") are to the lawful currency of the United Kingdom. All references in this announcement to "$" are to the lawful currency of the United States.

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