Tax Planning Services

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,...

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...

Property Investment 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 Tax Technology & Data Tax Treaties Taxation Services

Property Tax and Stamp Duty: What Every Property Owner, Developer, and Investor Must Know

April 6, 2026by Dr Dawkins Brown

The Tax Dimension of Every Property Decision Land is one of the most significant assets in the Caribbean economy. From the family home to the commercial plaza, from the agricultural smallholding to the large industrial facility, from the hotel resort to the residential development — property ownership and property transactions carry a tax dimension that...

Tariffs & Supply Chain 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 Tax Technology & Data Tax Treaties

Tax Treaties and Cross-Border Structuring: Navigating Jamaica’s Treaty Network and Avoiding Double Taxation

April 6, 2026by Dr Dawkins Brown

The Treaty as a Tax Planning Tool and Compliance Obligation Double taxation — the imposition of tax on the same income by two different jurisdictions — is one of the most significant barriers to cross-border investment. A Jamaican company that receives dividends from a UK subsidiary faces potential taxation in both the UK (as...

BEPS Caribbean advisory services Cross-Border Tax Tax Advisory Tax Audit Tax Compliance Tax Dispute Resolution Tax Firm Tax Incentives Tax Planning Tax Planning Services Transfer Pricing Transfer Pricing & Regulatory Compliance

Transfer Pricing and BEPS: What Every Caribbean Group Must Know About Cross-Border Tax

April 5, 2026by Dr Dawkins Brown

The International Dimension of Caribbean Tax For Caribbean businesses with operations in a single domestic market — a Jamaican retailer selling to Jamaican customers, a Barbadian service provider with no overseas operations — transfer pricing and the OECD’s Base Erosion and Profit Shifting (BEPS) framework may appear to be remote concerns. But for the...

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

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

Tax Treaties and Cross-Border Structuring: Navigating Jamaica’s Treaty Network and Avoiding Double Taxation

June 3, 2026Board Minutes and Tax Substance: Why Documentation Can Make or Break a Holding Company Structure

June 3, 2026When Is a Holding Company a Conduit? Understanding Beneficial Ownership and Anti-Avoidance Risk

June 3, 2026Substance Beats Formality: What the Milan Tax Court’s Luxembourg Holding Ruling Means for Cross-Border Tax Planning

June 1, 2026The Hidden Systems Challenge of IFRS 20: Why Data, Controls and Audit Readiness Matter

June 1, 2026IFRS 20 and EBITDA: Why Lenders, Investors and Boards Must Pay Attention

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