Tax Risk Management

International Business & Trade International Tax International Tax & Cross-Border International Tax Advisory Tax Incentives Tax Litigation Tax Objections Tax Planning Tax Planning Services Tax Risk Tax Risk Management Tax Strategy

Treaty Access Under Scrutiny: Substance, Beneficial Ownership and Principal Purpose Risk

June 7, 2026by Dr Dawkins Brown

Treaty access used to be a paperwork question. It is now an evidence question. The entity that cannot show genuine substance, beneficial ownership, and commercial purpose may hold a residency certificate and still lose the benefit it relies on. EXECUTIVE SUMMARY Double tax treaties remain essential tools in international business: they reduce withholding tax, allocate...

Board Minutes and Tax Substance: Why Documentation Can Make or Break a Holding Company Structure

June 3, 2026by Dr Dawkins Brown

Executive Summary In modern international tax planning, documentation is no longer an administrative afterthought. It is a central part of tax defence. Holding companies, investment platforms, regional headquarters, and cross-border ownership structures may be legally valid, but they remain exposed if the evidence does not prove that they are commercially real. The recent Milan...

When Is a Holding Company a Conduit? Understanding Beneficial Ownership and Anti-Avoidance Risk

June 3, 2026by Dr Dawkins Brown

Key Insight: A holding company is not vulnerable merely because it is lean. It becomes vulnerable when it lacks real substance, decision-making autonomy, commercial purpose, and evidence that it controls the income or assets it legally holds. Executive Summary Holding companies remain valuable tools in international tax and corporate structuring. They can support investment management,...

Corporate Structuring Cross-Border Business Dawgen Global Tax Insights Tax Administration & Policy Tax Advisory Tax Audit Tax Controversy Tax Dispute Resolution Tax Disputes Tax Risk Management Tax Strategy Tax Technology Tax Technology & Data Tax Treaties

Substance Beats Formality: What the Milan Tax Court’s Luxembourg Holding Ruling Means for Cross-Border Tax Planning

June 3, 2026by Dr Dawkins Brown

Executive Summary International tax planning is entering a new era in which paper structures are no longer sufficient, but genuine commercial substance remains powerful. A recent ruling by the First Instance Tax Court of Milan provides an important reminder that foreign holding companies should not automatically be disregarded simply because they are lean, investment-focused...

Actuarial Advisory Actuarial Services Advisory Services Business Resilience Business Restructuring Business Strategy Business Strategy & Transformation Caribbean Business Advisory CFO Advisory & Finance IFRS & Financial Reporting IFRS 17 Reserving & Valuation Risk Advisory Services Risk Assurance & Advisory Risk Management risk management in Caribbean restructuring Tax Risk Management The Caribbean Resilience Playbook

IFRS 17, Three Years On: What Caribbean Insurers Got Right, What They Got Wrong, and What Comes Next

May 20, 2026by Dr Dawkins Brown

The technical transition is largely complete. The strategic transition is not. An honest assessment of where the region stands — and the five priorities for the next 24 months IFRS 17 became effective for accounting periods beginning 1 January 2023. For Caribbean insurers, that meant three years of implementation work, hundreds of millions in cumulative...

Designing a Pan-Caribbean Tax Operating Model for a Multi-Jurisdictional Group

April 19, 2026by Dr Dawkins Brown

C | Context A diversified Caribbean group, built over three decades through a combination of organic expansion and strategic acquisition, had accumulated a multi-jurisdictional footprint whose tax management had not kept pace with its commercial development. The group’s fourteen legal entities, spread across six Caribbean jurisdictions, were each managed by local finance teams operating under...

Tax Disputes Tax Firm Tax Incentives Tax Litigation Tax Objections Tax Planning Tax Planning Services Tax Risk Tax Risk Management Tax Strategy Tax Technology Tax Technology & Data Tax Treaties Taxation Services

Tax Strategy and Governance: Building a World-Class Tax Function for Caribbean Businesses

April 6, 2026by Dr Dawkins Brown

From Compliance to Strategy Eleven articles ago, this series opened with a foundational proposition: that tax is not a fixed cost to be simply paid, but a managed variable — shaped by how well the organisation understands its obligations, how proactively it plans its structures and transactions, and how rigorously it maintains the compliance...

Tax Administration & Policy Tax Advisory Tax Audit Tax Compliance Tax Dispute Resolution Tax Firm Tax Incentives Tax Litigation Tax Planning Tax Planning Services Tax Risk Tax Risk Management Tax Strategy Tax Technology Tax Technology & Data Tax Treaties Taxation Services

Tax Disputes and Objections: How to Challenge a TAJ Assessment and Navigate the Appeals Process

April 6, 2026by Dr Dawkins Brown

When TAJ and the Taxpayer Disagree Receiving a tax assessment from Tax Administration Jamaica is one of the most consequential financial events a Caribbean business or individual can face. The assessment sets out TAJ’s determination of the tax liability for a particular period — a determination that may include additional tax, interest, and penalties that,...

CRS and FATCA Compliance: What Caribbean Financial Institutions and Account Holders Must Know

April 6, 2026by Dr Dawkins Brown

The End of Financial Privacy as a Tax Planning Tool For decades, offshore financial accounts served a dual purpose for many Caribbean and international investors: a store of wealth beyond the reach of domestic tax authorities, and a mechanism for sheltering investment returns from the income tax obligations that would apply if those returns were...

Securities Dealers Tax Administration & Policy Tax Advisory Tax Audit Tax Compliance Tax Dispute Resolution Tax Firm Tax Incentives Tax Planning Tax Planning Services Tax Risk Tax Risk Management Tax Strategy Tax Technology

Financial Services Taxation: Sector-Specific Tax Obligations for Banks, Insurance Companies, Credit Unions, and Securities Dealers

April 6, 2026by Dr Dawkins Brown

Why Financial Services Taxation Requires Specialist Expertise The taxation of financial institutions in Jamaica and across the Caribbean is more complex, more consequential, and more frequently mismanaged than the taxation of any other sector. The financial services sector encompasses institutions with vastly different tax profiles — commercial banks subject to the higher 33.33% CIT...

Treaty Access Under Scrutiny: Substance, Beneficial Ownership and Principal Purpose Risk

Board Minutes and Tax Substance: Why Documentation Can Make or Break a Holding Company Structure

When Is a Holding Company a Conduit? Understanding Beneficial Ownership and Anti-Avoidance Risk

Substance Beats Formality: What the Milan Tax Court’s Luxembourg Holding Ruling Means for Cross-Border Tax Planning

IFRS 17, Three Years On: What Caribbean Insurers Got Right, What They Got Wrong, and What Comes Next

Tax Strategy and Governance: Building a World-Class Tax Function for Caribbean Businesses

Tax Disputes and Objections: How to Challenge a TAJ Assessment and Navigate the Appeals Process

CRS and FATCA Compliance: What Caribbean Financial Institutions and Account Holders Must Know

Financial Services Taxation: Sector-Specific Tax Obligations for Banks, Insurance Companies, Credit Unions, and Securities Dealers

July 6, 2026How to Build Governance into a Family-Owned Business

July 6, 2026How to Formalize: From Hustle to Registered, Bankable Business

July 6, 2026How to Escape Strategic Drift: When Your Business Is Busy but Going Nowhere

July 5, 2026AI Incident Response: What Happens When an AI System Fails?

July 5, 2026AI Vendor Risk Management: The Hidden Exposure in Third-Party Platforms

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