Tax Risk Management

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A 90-Day Digital Tax Readiness Plan for Caribbean Groups

October 4, 2026by Dr Dawkins Brown

A group that starts in October 2026 can finish a disciplined readiness programme before Jamaica’s planned digital tax commencement in early 2027. Here is what each month should deliver, who owns what, and how the board will know it worked. Executive summary Digital tax readiness is not a legal memorandum. It is an owner, a...

Who Collects Tax When a Platform Sits in the Middle

September 29, 2026by Dr Dawkins Brown

Marketplaces, booking sites and delivery apps now stand between Caribbean sellers and their customers. The law increasingly decides who collects the tax by who controls the transaction, not by who owns the product. Sellers who assume “the platform handles it” are carrying risk they have not measured. Executive summary A single online sale can involve...

Caribbean Risk Horizon Caribbean tax modernisation and tokenization Caribbean Tax Planning Caribbean Tax Planning Firm Cross-Border Business Cross-Border Regulation Cross-Border Tax Digital Tax Digital Tax Transformation Digital Transformation Indirect Tax Tax Planning Services Tax Risk Management Tax Strategy Tax Technology Tax Technology & Data Technology & Transformation VAT & GCT

VAT at the Customer’s Doorstep: How Digital Tax Follows the Customer Across the Caribbean

September 29, 2026by Dr Dawkins Brown

Consumption tax on digital services follows the customer, not the supplier. For Caribbean firms selling across the islands, that principle turns on three practical questions: is the customer a business, where are they, and who collects? Executive summary Every Caribbean consumption tax regime for digital services rests on one idea: value added tax (VAT) or...

Digital Tax Digital Tax Transformation digital token digital transformation & virtual solutions Digital-First CFO Services Digitalization Tax Planning Services Tax Risk Tax Risk Management Tax Strategy Tax Technology Tax Technology & Data Tax Treaties Taxation Services

Jamaica’s GCT on Foreign Digital Services: What Changes in 2027

September 29, 2026by Dr Dawkins Brown

Most Jamaican businesses already pay GCT on imported services through the reverse charge. The Budget measure is aimed at households and unregistered buyers, and its design will decide whether registered businesses are taxed twice. Executive summary Jamaica’s Budget for fiscal year (FY) 2026/27 proposes to apply General Consumption Tax (GCT) to digital services and intangibles...

Digital Foundations Series Digital Tax Digital Tax Transformation Digital Transformation Tax Controversy Tax Firm Tax Litigation Tax Planning Tax Risk Management Tax Strategy Tax Technology Tax Technology & Data Tax Treaties Taxation Services

The Caribbean Digital Tax Moment

September 29, 2026by Dr Dawkins Brown

Jamaica’s Budget, Grenada’s new law and years of quiet collection in Barbados and The Bahamas mean digital tax is no longer a foreign debate. It is a Caribbean compliance question, and boards need a method to answer it. Executive summary Until recently, “digital tax” in the Caribbean meant headlines from Paris, London and Ottawa. In...

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...

A 90-Day Digital Tax Readiness Plan for Caribbean Groups

Who Collects Tax When a Platform Sits in the Middle

VAT at the Customer’s Doorstep: How Digital Tax Follows the Customer Across the Caribbean

Jamaica’s GCT on Foreign Digital Services: What Changes in 2027

The Caribbean Digital Tax Moment

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

October 5, 2026Taxed Like Europe? What the World's Tax Rankings Really Say About the Caribbean

October 4, 2026CAREERS AT DAWGEN GLOBAL: Attorneys-at-Law — Legal & Compliance Division

October 4, 2026Six Tools, No Team

October 4, 2026The Breach Begins Before the Login

October 4, 2026A 90-Day Digital Tax Readiness Plan for Caribbean Groups

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