Proposed Tender Offer and Notice of GM

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 £7.3 million to Shareholders by way of a tender offer at 238p 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 £7.3 million in cash at 238 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 16.7 per cent. to the middle market closing price of an Ordinary Share on 25 September 2025.

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, the Board has decided to make a distribution of up to £7,263,793 to Shareholders by way of a tender offer based on the latest NAV per Ordinary Share.

We have used Q2 2025 NAV for the purposes of the Tender Offer as published in our Interim Report and Financial Statements for the six months ended 30 June 2025 on 29 September 2025

Accordingly, the Board has resolved to make a distribution of up to £7,263,793 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 10.00 a.m. on 24 October 2025 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 and increase in cap on Directors' fees. 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.

EXPECTED TIMETABLE

PROPOSED PURCHASE OF UP TO 3,052,013 ORDINARY SHARES REPRESENTING APPROXIMATELY 3.9 PER CENT. OF THE COMPANY'S ISSUED SHARE CAPITAL AT A PRICE OF 238 PENCE PER ORDINARY SHARE AND NOTICE OF GENERAL MEETING (to authorise the Tender Offer and to increase the cap on Directors' fees)

Introduction

The Company intends to undertake return of capital of up to £7,263,793 through a tender offer by Deutsche Numis to Qualifying Shareholders and subsequent repurchase by the Company from Deutsche Numis of the Ordinary Shares successfully tendered (the "Tender Offer").

The Tender Offer will be conducted at a fixed price of 238 pence per Ordinary Share (the "Tender Price"), based on the latest NAV for the Company and which represents a premium of approximately 16.7 per cent. to the middle market closing price of an Ordinary Share on 25 September 2025 (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 3.9 per cent. of the Company's current issued share capital. The Company is seeking authority to buy back up to 3,052,013 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 10.00 a.m. on 24 October 2025, 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.

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 2024, the Board has decided to make a distribution of up to £7,263,793 to Shareholders by way of a tender offer based on the latest NAV per Ordinary Share.

We have used Q2 2025 NAV for the purposes of the Tender Offer as published in our "Interim Report and Financial Statements for the six months ended 30 June 2025" on 29 September 2025

Accordingly, the Board has resolved to make a distribution of up to £7,263,793 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.

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 3,052,013 Ordinary Shares, representing approximately 3.9 per cent. of the Ordinary Shares in issue on the Record Date;
• each Qualifying Shareholder will be entitled to tender up to 3.9 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"). Excess Tenders will only be accepted to the extent that other Qualifying Shareholders tender less than their Basic Entitlement or do not tender any Ordinary Shares. At the Company's discretion, 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; and
• the Tender Price will be fixed at 238 pence per Ordinary Share which represents a premium of approximately 16.7 per cent. to the middle market closing price of an Ordinary Share on 25 September 2025, the Latest Practicable Date before the printing of the Circular.

Structure of the Tender Offer

The Tender Offer will be implemented on the basis of Deutsche Numis acquiring, as principal, the successfully tendered Ordinary Shares at the Tender Price. The Company will purchase such Ordinary Shares from Deutsche Numis 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 3,052,013 Ordinary Shares will be purchased under the Tender Offer, representing approximately 3.9 per cent. of the Company's current issued share capital, for a maximum aggregate consideration of £7,263,793. 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 Deutsche Numis 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. At the Company's discretion, 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. 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 2025 and tenders received after that time will not be accepted (unless the Tender Offer is extended).

The Tender Price

A Tender Price of 238 pence per Ordinary Share will be applied to all Ordinary Shares purchased by Deutsche Numis pursuant to the Tender Offer. The Tender Price will allow Deutsche Numis to purchase the maximum number of Ordinary Shares for a total cost not exceeding £7,263,793 or, if the aggregate price of all Ordinary Shares validly tendered by Qualifying Shareholders is less than £7,263,793, 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 3.9 per cent. of their holding (rounded down to the nearest whole number of Ordinary Shares) held at the Record Date to be purchased by Deutsche Numis 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 £7,263,793, 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 3,052,013 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 2025. Successfully tendered Ordinary Shares will be purchased free of commission and dealing charges. Any Ordinary Shares repurchased by the Company from Deutsche Numis following the purchase by Deutsche Numis 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 Deutsche Numis, to extend the period during which the Tender Offer is open, based on market conditions and/or other factors.

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 3.9 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.

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 3,052,013 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; and
• all Ordinary Shares validly tendered by Qualifying Shareholders in excess of their Basic Entitlements will, at the Company's discretion, 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.

The number of Ordinary Shares to be purchased in the Tender Offer will not, in any event, exceed 3,052,013 Ordinary Shares.

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:

• the Tender Offer not having been terminated in accordance with its terms and the Company having confirmed to Deutsche Numis that it will not exercise its right to require Deutsche Numis not to proceed with the Tender Offer; and
• Deutsche Numis 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 Deutsche Numis 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 Deutsche Numis, 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 Deutsche Numis, 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 2025; or (b) by a CREST payment (for CREST Shareholders only), expected to be made on or around 3 November 2025, 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.

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 3,052,013 Ordinary Shares, representing approximately 3.9 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 of by proxy.

Repurchase Agreement

Under the Repurchase Agreement, the parties have agreed that, subject to, amongst other things, the sum of up to £7,263,793 (equal to the Tender Price multiplied by the maximum number of Ordinary Shares that could be repurchased under the Tender Offer) being received by Deutsche Numis (or its custodian) by no later than 5 p.m. on 28 October 2025 (or such later time and/or date as may be agreed by Deutsche Numis and the Company) and the Tender Offer becoming unconditional in all respects and not lapsing or terminating in accordance with its terms, Deutsche Numis 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 £7,263,793.

The Company has agreed that, immediately following the purchase by Deutsche Numis of all Ordinary Shares which it has agreed to purchase as principal under the terms of the Tender Offer, the Company will purchase from Deutsche Numis 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 Deutsche Numis 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 Deutsche Numis and incorporates a customary indemnity in favour of Deutsche Numis in respect of any liability which it may suffer in relation to the performance of its obligations under the Tender Offer.

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.

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.

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 Deutsche Numis 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.

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 10.00 a.m. on 22 October 2025. 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 10.00 a.m. on 22 October 2025. 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.

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 2025. 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.

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 2025.

General Meeting and Resolutions

A general meeting of the Company will be held at the offices of Helios Underwriting PLC, 1st Floor, 33 Cornhill, London, United Kingdom EC3V 3ND at 10.00 a.m. on 24 October 2025 to consider the Resolutions. Notice of the meeting is at the end of the Circular.

Increase in cap on Directors' fees

Resolution 1, which is an ordinary resolution requiring at least a simple majority of the votes cast on a poll (whether in person or by proxy) to be in favour, seeks authority to increase the cap on Directors' fees (such fees being distinct from any salary or remuneration payable to any Director under a service agreement or other amount payable to any Director pursuant to other provisions of the Company's Articles) from £100,000 per annum to £500,000 per annum, all in accordance with Article 88. The existing cap of £100,000 has not been increased since 2006 and is now considered by the Board to be inadequate to enable the Company to recruit and retain the high calibre and number of non-executive directors it now requires as a more mature company. Furthermore, from 2026, the Company will have a remuneration policy governing all Director remuneration (including limits) which will be the subject of a triennial advisory shareholder vote at the Company's annual general meeting.

Tender Offer Resolution

Resolution 2, which is a special resolution, seeks authority to make market purchases of Ordinary Shares in connection with the Tender Offer. The 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, Resolution 2 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.

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 72,637,931 Ordinary Shares.

Deutsche Numis and Deutsche Bank have each 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.

Related party transaction

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

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 3,052,013 Ordinary Shares to 69,585,918 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 Deutsche Numis in relation to the Tender Offer.

Further information

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

Recommendation

The Board considers the Resolutions to be in the best interests of Shareholders as a whole. Accordingly, the Board recommends that Shareholders vote in favour of the Resolutions to be proposed at the General Meeting, as the Directors intend to do for their respective individual beneficial holdings of, in aggregate, 22,992,406 Ordinary Shares, representing approximately 31.7 per cent. of the Company's issued share capital, carrying voting rights, 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.

DEFINITIONS

The following definitions apply throughout the Circular unless the context otherwise requires:

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.