Tax Technology

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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...

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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...

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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...

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,...

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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...

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...

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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,...

A 90-Day Digital Tax Readiness Plan for Caribbean Groups

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

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

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

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