Rosana Bailey

Rosana acts in a wide range of commercial and chancery disputes, including:

· Contractual disputes and commercial agreements

· Shareholder, partnership and joint venture disputes

· Breach of fiduciary duty and misrepresentation

· Trusts, wills and probate (contentious and non-contentious)

· Property-related commercial litigation

· Cross-border commercial disputes

· Enforcement, interim relief and urgent applications

· Employment disputes arising in commercial, fiduciary or insolvency contexts

Her approach is characterised by meticulous preparation, strategic foresight and the ability to manage complex litigation with clarity, tenacity and composure.

Rosana’s cross-border practice encompasses both English cases with international dimensions and standalone overseas litigation. In addition to managing litigation that spans multiple jurisdictions, she is frequently appointed to lead cases in foreign courts by clients and professionals who have worked with her in England and who seek to rely on the competencies demonstrated in her domestic High Court practice.

Her international work includes preparing originating documents, pleadings, witness statements and legal submissions for use in foreign courts and liaising closely with overseas attorneys who present her material abroad. She coordinates the overall litigation strategy where proceedings run in parallel across jurisdictions, ensuring that evidence, procedural steps and legal arguments remain consistent and mutually reinforcing.

Rosana is experienced in navigating differing procedural landscapes, corporate structures and legal systems. She leads multijurisdictional teams with clarity and cohesion, ensuring that complex international disputes progress in a structured, strategically unified and commercially focused manner.

Rosana advises and acts in all aspects of real property litigation, including:

· Co-ownership and trusts of land

· Boundary disputes and rights of way

· Proprietary estoppel

· Mortgages, secured lending and bridging loan disputes

· Commercial and residential landlord and tenant

· Development disputes

· Nuisance and trespass

· Enforcement and possession proceedings

· Council tax liability disputes and enforcement issues

She drafts and negotiates tenancy agreements, retrospective licences, commercial leases and bespoke property-related contracts.

Her insolvency practice covers both personal and corporate matters, including:

· Bankruptcy petitions and statutory demands

· Winding-up petitions

· Misfeasance and antecedent transaction claims

· Directors’ duties and insolvency-related breaches

· Cross-border insolvency issues

· Applications under the Insolvency Act 1986

· Asset recovery and tracing

· Disputes involving bridging loans, receivership appointments and enforcement of secured lending

Her commercial background strengthens her ability to navigate complex financial and factual scenarios.

Rosana advises on and litigates:

· Validity of wills

· Undue influence and lack of capacity

· Construction and rectification of wills

· Inheritance Act 1975 claims

· Executor and trustee disputes

· Estate administration issues

· Contentious probate proceedings

She is frequently instructed to interpret complex testamentary provisions and to advise on high-value estate disputes.

Rosana’s litigation practice is defined by a comprehensive, hands-on approach. She appears regularly in the High Court and has acted in complex, high-value litigation across the Chancery and King’s Bench Divisions, and in the Court of Appeal. She:

· Conducts detailed initial consultations to understand the client and the strategic landscape

· Assesses settlement prospects at an early stage

· Drafts all key documents, including pleadings, witness statements, affidavits, skeleton arguments and grounds of appeal

· Manages disclosure, applications, directions and procedural steps

· Appears in court at all stages, including interim hearings, trials and appeals

· Leads cases from start to finish, whether instructed by solicitors or directly by clients

Rosana regularly advises on:

· Contractual interpretation

· Commercial agreements

· Trusts and wills

· Property rights

· Insolvency issues

· Cross-border disputes

In addition, she undertakes specialist drafting work for governmental and public bodies, including contributing to policy development projects in the Caribbean. Her written advice is known for clarity, attention to detail and practical application.

Rosana drafts:

· Commercial contracts

· Banking agreements

· Tenancy agreements

· Retrospective licences

· Commercial leases

· Bespoke agreements for business clients

· Oil contracts

Her drafting is informed by extensive litigation experience, giving her a strong understanding of how contractual provisions operate in practice.

Rosana has extensive experience in negotiation and ADR, including leading settlement discussions in multi-party disputes and advising clients through mediation. Her strategic approach and detailed preparation enable clients to achieve commercially effective outcomes.

Rosana drafted the original Pupillage Policy for Chambers in her former roles as Head of the Pupillage Committee and member of the Management Committee. She has delivered structured sessions on litigation strategy, drafting and case preparation, drawing on her extensive High Court experience.

She produces specialist written material for clients, including detailed legal analyses, policy drafting for governmental bodies and structured guidance on litigation processes. Additionally, she prepares commentary on developments in property and chancery law for professional audiences, and her written work has informed Parliamentary Select Committee discussions.

Rosana frequently acts in disputes that cross traditional boundaries between commercial, chancery, property and public law. Her ability to integrate principles from multiple areas enables her to provide comprehensive and strategically coherent advice in cases involving overlapping legal and factual issues.

Rosana is experienced in managing cases involving extensive documentary and witness evidence, including multi-volume trial bundles, cross-border factual issues and expert evidence. Her thorough approach ensures that complex cases are presented with clarity and precision.

Rosana is committed to access to justice and has delivered public legal education sessions for affected communities, including detailed briefings on litigation processes and rights following major national incidents.

Her longstanding pro bono commitment includes:

· Acting for a borrower in a bridging loan repossession case from 2015 to 2020, including the Court of Appeal

· Successfully representing two council tenants in possession proceedings in 2021 and 2022

· Former Head of the Pupillage Committee

· Former Member of Chambers’ Management Committee

· Original Author of Chambers’ Pupillage Policy

· Led an expanded recruitment process to widen access and opportunity

Chancery Bar Association

The Commercial Bar Association – COMBAR

Historical architecture

Notable Cases

Commercial & Chancery

Credit Capital Corporation Ltd v Watson & Market Financial Solutions Ltd

[2021] EWHC 1136 (QB)

Dispute concerning bridging finance, alleged misrepresentation and the operation of the unfair relationship provisions under the Consumer Credit Act 1974.

Ryan v HNW Lending Ltd

[2019] EWHC 2289 (Ch)

High Court claim addressing secured lending, enforcement and the proper calculation of interest on a bridging loan.

Adelekun v HMRC

TC/2016/03724 (2019); [2020] UKUT 0244 (TCC)

Tax appeal concerning VAT registration, service provision and the admission of fresh evidence before the Upper Tribunal.

Blaine v Touchstone Corporate Ltd

[2025] EWHC 982 (Ch)

Appointed to perform urgent redrafting following a strike‑out application in a complex commercial dispute, enabling the claim to proceed.

SCT Finance Limited v Bolton

[2002] EWCA Civ. 56; [2003] 3 All ER 434; [2002] All ER (D) 75 (Jan)

The Court of Appeal removed an arbitrary £15,000 costs cap, holding that proportionality is secured through standard‑basis assessment, not judicial ceilings.

Property, Housing & Public Law Adjacent

Okon v London Borough of Lewisham

[2016] EWHC 864 (Ch); [2017] EWHC 1933 (Admin); [2017] EWCA Civ. 1973

Clarified the interaction between council tax liability orders, valuation tribunal jurisdiction and bankruptcy proceedings.

Amin v London Borough of Redbridge & Atkinson (Trustee in Bankruptcy)

[2018] EWHC 3100 (Ch); [2019] RVR 133; [2019] BPIR 1

Significant insolvency appeal concerning rescission of a bankruptcy order founded on council tax liability and the circumstances in which costs are payable.

Enayathulla v London & Quadrant Housing Trust

[2023] Valuation Office Agency, 8 November 2023

Housing dispute concerning valuation evidence and the evidential framework governing assessments by social landlords.

Wills, Estates & Family Property

Bhatti v Bhatti & Others

[2022] Claim No. PT‑2021‑000192 (High Court)

Multi-party family property and trust dispute involving allegations of undue influence and beneficial ownership.

Allen v Kelly, Neighbourcare St John’s Wood and Maida Vale and Age UK Westminster

(2022) Claim No. PT‑2022‑000980

Inheritance Act claim resolved prior to trial, preserving the estate for the beneficiaries.

Smith and Smith v Thompson and Thompson

Case No. PT‑2019‑BRS‑000102 (High Court, 2021)

Family property dispute concerning the creation and recognition of a constructive trust.

Multi-Party & Public Interest Litigation

Kaminskas and Liliu v Southern Gas Network

[2025] (settled pre‑issue)

Lead counsel in litigation arising from the 2022 Galpin’s Road gas explosion; settlement achieved without the need for proceedings.

Cross‑Border & Appellate Leadership

Bhatti v Bhatti & Bhatti (Appeal)

Petition No. 22 of 2020; Appeal No. E217 of 2020 (Kenyan Court of Appeal)

Cross‑jurisdictional appeal involving complex procedural issues and appellate strategy.

Nabb Brothers Ltd v Lloyds Bank International (Guernsey) Ltd

[2005] EWHC 405 (Ch)

Service‑out and forum dispute concerning a Ghanaian company, with the English court upholding jurisdiction over a Guernsey‑based bank.