“Holly’s advocacy is clear, focused and direct. Clients find her engaging.”

Legal 500 (2025)

  • Chancery Bar Association
  • Contentious Trusts Association
  • BVI Bar Association
  • The Honourable Society of Gray’s Inn
  • BPTC with LLM (Distinction), BPP Law School (2019)
  • LLB Law (First Class), Newcastle University (2018)

Holly Challenger is a self-employed, independent barrister whose practice is regulated by the Bar Standards Board [Bar Council Ref 71987]. She is fully insured with the Bar Mutual Indemnity Fund [BMIF Ref 2360/090] to provide legal services; please refer to the BMIF website for full details of the world-wide cover provided. Holly is registered for VAT under the reference 518628863.

Holly is a specialist private client practitioner, working both onshore and offshore. Having initially spent several years in England developing an onshore practice, Holly was called to the Bar of the British Virgin Islands in July 2024, and subsequently spent almost two years working as an Associate in the Dispute Resolution team of a leading offshore firm in the BVI. During that time, she gained experience in a variety of offshore and cross-border matters. She regularly appeared (both led and unled) before the BVI High Court and Commercial Court in respect of trusts and estates litigation. Holly holds a current BVI practising certificate.

Holly was ranked as a ‘Rising Star’ by the Legal 500 in both the 2024 and 2025 editions for her English private client work. She is described as ‘very knowledgeable about the law relating to probate claims’.

Holly is an effective advocate and has significant experience in the English High Court and County Courts. She is comfortable working unled in respect of complex matters, but is equally comfortable being led as part of a larger team. The Legal 500 describes her as a “junior with a collaborative approach”.

Holly’s practice focuses on:

  • Advising on the interpretation and effect of wills and trusts;
  • Advising trustees and personal representatives on the scope, exercise, and delegation of fiduciary powers;
  • Bringing and defending applications under section 116 Senior Courts Act 1981;
  • Claims regarding testamentary capacity and/or want of knowledge and approval;
  • Claims arising from allegations of undue influence and/or fraudulent calumny;
  • Claims by beneficiaries for an account (and consequential relief);
  • Disputes concerning the proper construction and/or rectification of wills;
  • Bringing or defending claims seeking the removal and/or replacement of personal representatives and trustees;
  • Applications under Part 64;
  • Investigating and advising on lifetime transactions procured by undue influence;
  • Claims under the Inheritance (Provision for Family and Dependants) Act 1975;
  • Proprietary estoppel claims;
  • Breach of trust claims;
  • Offshore and cross-border trusts and estates litigation; and
  • Advising in respect of various non-contentious issues in respect of trusts and estates.

Holly is a member of the Chancery Bar Association, the Contentious Trusts Association, and the BVI Bar Association.

Expertise

Holly has significant experience dealing with contentious private client matters, both onshore and offshore. Some examples of her work include:

  • ATH v BNU BVIHPB2024/0170 (10 July 2025) – led by Dakis Hagen KC, successful in seeking a declaration that BNU was not, and had never been, the personal representative of SSQ in the BVI. This resulted in the derivative proceedings which BNU had launched being declared a nullity, and the freezing injunction obtained by BNU for US$268million being discharged.
  • Culgoa Limited v Basement Investments Limited BVIHCMAP2024/0011 (26 February 2026) – led by David Brownbill KC in the Eastern Caribbean Court of Appeal. Successful in responding to an appeal regarding the construction of a share transfer form, where the central question was whether certain shares were held by Basement on express bare trust for Culgoa.
  • Ramji v Harvey & Ors [2023] EWHC 1664 (Ch); [2024] 1 P & CR DG 11 – appeared unled in respect of a five-day trial in the High Court in London, acting on behalf of the Second, Third and Eighth Defendants. Undue influence successfully proven in relation to a lifetime transaction, resulting in the transfer of a property valued at circa £900,000 being set aside. Further, successfully defended a claim for an interest in another of the deceased’s properties on the basis of a constructive trust.
  • Ramji v Harvey & Ors [2023] EWHC 1937 (Ch); [2023] Costs LR 1047 – successful in seeking an award of indemnity costs on the basis that the Claimant and Ninth Defendant had given false evidence in pursuit of financial gain.
  • Steels v Steels & Anor [2023] EWHC 2985 (Ch); [2023] All ER (D) 124; [2024] EGLR 4 – acted for the Respondents in an appeal to the High Court in respect of a proprietary estoppel claim arising out of assurances that a property in which the parties lived would be passed to the Respondents on the death of the Appellant. The three-day first instance trial involved consideration of the decision in Guest v Guest, which was handed down on the first day of trial.
  • Advising the litigation friend of minor beneficiaries as to the suitability of a settlement in a substantial estate which was subject to a claim under the Inheritance Act by the deceased’s wife.
  • Advising as to meaning of ‘child of the family’ within section 1(1)(d) of the Inheritance Act, where the claimants had never known the deceased during their minority.
  • Acting for the claimant seeking permission to bring a claim out of time under section 4 of the Inheritance Act in an estate of over £6million.
  • Advising the executors of an estate as to the tax and other implications of a pension scheme. The executors sought advice as to whether a pension nomination made by the deceased during his lifetime was binding and the implications this would have on the inheritance tax payable in relation to the deceased’s estate.
  • Often advising as to the IHT and/or CGT implications of settlement agreements in respect of claims under the Inheritance Act.
  • Advising the settlor of a trust in relation to a difficult claim for recission, whereby she sought to have the trust declared void on the ground of mistake.
  • Advising as to the position in relation to unborn beneficiaries in the context of an application to bless a proposed distribution of trust assets.

Holly has a particular interest in offshore work, having spent almost two years working for a leading firm in the BVI. Some recent examples of her offshore work include:

  • ATH v BNU BVIHPB2024/0170 (10 July 2025) – led by Dakis Hagen KC, successful in seeking a declaration that BNU was not, and had never been, the personal representative of SSQ in the BVI. This resulted in the derivative proceedings which BNU had launched being declared a nullity, and the freezing injunction obtained by BNU for US$268million being discharged.
  • DUK v UGX & Ors BVIHC(COM)2024/0358 (16 September 2024)led by Richard Millet KC, acted for the Joinder Applicants (WKU, ZPP and AUZ) seeking to be joined to an application for leave to commence derivative proceedings on behalf of two BVI companies. The derivative leave application arose in the context of a wider dispute as to the administration of and succession to the BVI estate of the late SSQ, and where DUK had obtained a freezing injunction against WKU and ZPP.
  • Culgoa Limited v Basement Investments Limited BVIHCMAP2024/0011 (26 February 2026) – led by David Brownbill KC in the Eastern Caribbean Court of Appeal. Successful in responding to an appeal regarding the construction of a share transfer form, where the central question was whether certain shares were held by Basement on express bare trust for Culgoa.
  • Culgoa Limited v Basement Investments Limited BVIHCMAP2024/0011 (16 October 2025) – led by David Brownbill KC, successful in resisting an application made in the Eastern Caribbean Court of Appeal for the appellant to amend its statement of case, amend its grounds of appeal, and introduce new evidence on appeal.
  • Oasis Core Investment Fund Ltd & Ors v Hollysys Automation Technologies Ltd BVIHCOM2024/0619 – led by Richard Millett KC, appeared for the successful applicant in securing a declaration as to the proper interpretation of section 179(9) of the BVI Business Companies Act.
  • Appeared unled in the BVI High Court in respect of a contested application for a grant of letters of administration.
  • Successfully secured the replacement of a protector of a BVI trust on behalf of an UHNW client, following the breakdown in the relationship between the settlor and the protector.
  • Advised on various occasions as to the interpretation and application of certain provisions of the Eastern Caribbean Supreme Court (Non-Contentious Probate and Administration of Estates) Rules 2017.

Holly is regularly instructed in respect of non-contentious private client matters. Her experience includes:

  • Advising on the interpretation and effect of wills and trusts;
  • Drafting trust documents, including deeds of appointment, advancement, and retirement;
  • Advising trustees and personal representatives on the scope, exercise, and delegation of fiduciary powers;
  • Advising on and drafting post-death deeds of variation and deeds of appointment to mitigate inheritance tax;
  • Advising on the day-to-day administration of estates and trusts; and
  • Advising on and preparing section 116 Senior Courts Act 1981 passing-over applications.

Holly has experience advising in relation to charity law and incidental matters, including matters arising from bequests to charities within wills (in particular, construction disputes or issues arising from the misidentification of charitable beneficiaries).

She is comfortable advising in respect of the construction and validity of testamentary gifts to charities (including conditional, residuary and purpose-specific gifts), advising on failed charitable gifts (including circumstances where the named charity has ceased to exist, never existed or has been misdescribed) and advising on the application of the cy-près doctrine.

Holly has experience representing clients during various forms of ADR, particularly at mediation.

She is frequently instructed to:

  • Prepare position statements and attend mediations on behalf of clients;
  • Advise upon and draft offers and counter-offers;
  • Review and advise on existing settlement proposals; and
  • Prepare and review Deeds of Settlement, Tomlin Orders, Deeds of Variation and other formal documents once a compromise has been reached.

Holly is also experienced in preparing CPR 21.10 approval applications where matters involve minors or protected parties, and she can provide the required Opinion for the Court in such matters in order to ensure that settlements reached are properly enforceable.

 

"Holly Challenger is very knowledgeable about the law relating to probate claims"

Legal 500 (2025)

"A junior with a collaborative approach and a measured demeanour"

Legal 500 (2024)

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