Tax Administration & Policy

Caribbean Business Insights Caribbean Business Strategy Caribbean Tax Caribbean Tax Insights Caribbean tax modernisation and tokenization Caribbean Tax Planning Caribbean Tax Planning Firm Tax Administration & Policy Tax Advisory Tax Audit Tax Compliance Tax Controversy

Taxed Like Europe? What the World’s Tax Rankings Really Say About the Caribbean

October 5, 2026by Dr Dawkins Brown

The finding Jamaica collects tax equal to 25.6% of its GDP — more, as a share of its economy, than the United States (19.5%), Germany (23.0%), Japan (20.2%) or Switzerland (20.0%). Barbados, at 27.8%, collects more than Greece and sits on the global top-20 list beside the Nordic welfare states. That is the Caribbean story...

Dawgen Digital Tax COMPASS™Digital Tax Digital Tax Transformation digital token Digital Transformation Digital-First CFO Services Tariffs & Customs Tax Administration & Policy Tax Advisory Tax Audit Tax Compliance Tax Controversy Tax Dispute Resolution

Canada’s Reversal and the Uncertain Road to Pillar One

September 30, 2026by Dr Dawkins Brown

Canada enacted a digital services tax, reached back two years to collect it, then repealed it and refunded the money with interest. The episode is a lesson in legislative risk, and a signpost for Caribbean states choosing between the OECD, the United Nations and their own consumption taxes. Executive summary In June 2024 Canada enacted...

Corporate Income Tax Cross-Border Business Cross-Border Regulation Dawgen Digital Tax COMPASS™Dawgen Global Tax Insights Digital Assets Digital Assets & Blockchain Tax Administration & Policy Tax Advisory Tax Audit Tax Compliance Tax Dispute Resolution Tax Firm Tax Incentives Tax Litigation

Digital Services Taxes and the Price of Gross Revenue

September 29, 2026by Dr Dawkins Brown

A 2 or 3 per cent tax on revenue sounds modest until it is set against margin. Digital services taxes are expensive for thin-margin businesses, politically costly for the countries that levy them, and a poor fit for small Caribbean economies. Executive summary A digital services tax (DST) is a tax on the gross revenue...

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...

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...

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 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...

Tax Administration & Policy

Taxed Like Europe? What the World’s Tax Rankings Really Say About the Caribbean

Canada’s Reversal and the Uncertain Road to Pillar One

Digital Services Taxes and the Price of Gross Revenue

Who Collects Tax When a Platform Sits in the Middle

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 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

October 18, 2026The Caribbean Is at the Foundation Stage of AI

October 15, 2026Grow Again Without Betting Your House: Sustainable Business Growth After Recovery

October 14, 2026Find the Core That Earns: A 100-Day Business Turnaround Strategy | Dawgen Global

October 14, 2026Take Back Control of Your Cash in 14 Days: A Business Recovery Guide

October 12, 2026Find the Cash Already Hiding in Your Business

Where to find us?

Dawgen Social links