Doing Business
In The U.S.
–
Gain a clear understanding of U.S. tax triggers, filing requirements, and the treatment of U.S. entities.

Michael Cadesky and Dean Smith cover the challenges Canadians face when doing business in the U.S. They focus on what CPAs need to know, from identifying when a client has a U.S. tax obligation and how entity types affect the final outcome when clients expand into the U.S. market.

Get Access | $225
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On-Demand
On-Demand

2.5 Hours CPD
2.5 Hours CPD

2.5 Hours CPD
Exclusive

Course Overview

More Canadian businesses are exploring the U.S. market, but the tax rules that apply to them often come as a surprise. This course explains how the U.S. tax system interacts with Canadian rules and shows exactly when Canadian clients must file, register, or pay tax in the U.S. You will learn what “doing business in the U.S.” means in practice, how Permanent Establishment applies, and why state nexus rules often catch clients off guard. The session also demystifies LLCs, partnerships, and branch structures and explains how each of them is treated for Canadian tax purposes.

The focus is on clear explanations, practical scenarios, and guidance that CPAs can apply immediately. By understanding the rules and common problem areas, you will be better equipped to prevent surprises, support informed decision-making, and advise clients confidently as they expand into the U.S. market.
Learning Objectives
1
Understand the activities that create U.S. tax exposure for Canadian individuals and corporations.
2
Compare U.S. entity types and understand their Canadian tax treatment.
3
Understand how the Canada U.S. Tax Treaty affects filing requirements and tax exposure.
4
Navigate the basic filing obligations for individuals, corporations, partnerships, and owners of U.S. entities.

Seminar Snapshot

Date Recorded
June 2025
Presentation
■ Yes
Slides
■ Yes
Detailed Notes
■ Yes
Technical Corner
■ No
Teach Test
■ No
Resources
■ No
Included in Archive
■ NO

CANADA & U.S. CROSS-BORDER TAX

Duration
2.5 hours + Optional Q&A Recording
CPD CPD Certificate
Category
International Tax
Doing Business in the U.S. walks through the practical tax issues Canadian CPAs encounter when clients earn income south of the border. The session is built for CPAs who want practical knowledge they can use immediately.
After completing this program, you will be confident with:
  • Determining whether a client has U.S. tax exposure at either the federal or state level
  • Explaining the Canadian consequences of using U.S. entities, including LLCs
  • Reviewing client activities and spotting filing requirements early
  • Applying Treaty rules to decide if U.S. tax applies
  • Helping clients avoid unexpected tax and penalties
This course is essential if you are responsible for:
  • Advising clients who operate, invest, or hire in the U.S.
  • Preparing or reviewing cross-border personal or corporate tax filings
  • Guiding clients through business expansion decisions
  • Handling U.S. information slips, partnership interests, or LLC ownership

Meet Your Presenters

Michael Cadesky

Michael Cadesky

FCPA, FCA, FTIHK, CTA, TEP (EMERITUS)

Michael Cadesky is the managing partner at Cadesky Tax and a committed contributor to the tax and accounting professions since 1980, earning the title of Fellow from CPA Ontario. He is a past governor of the Canadian Tax Foundation, past chair of STEP Canada and STEP Worldwide, and past chair of the CPA Canada Tax Committee for Small and Medium-Sized Enterprises. Michael is also the co-author of 11 books on tax subjects and the author or co-author of numerous papers and articles on Canadian and international taxation.

Hugh Woolley

Dean Smith

PhD, CFP, TEP, CPA, CA, RWM

As the President of Cadesky U.S. Tax Ltd., Dean has been providing U.S./Canada cross-border planning and compliance for over 30 years. He assists private clients with their personal, corporate, and estate planning needs taking into account the unique challenges of integrating two independent tax systems.
Frequently Asked Questions
Once you complete your purchase, you will create your account if you haven't already. You can access the course anytime through our platform. All Cadesky Tax Seminars programs come with one-year access.
Yes. This course is eligible for verifiable CPD hours for Canadian CPAs. A downloadable Certificate of Completion will be available once you complete all required modules.
Our programs are designed for CPAs and tax professionals who want to deepen their technical expertise. While no prerequisites are required, a working knowledge of Canadian tax will help you get the most out of the material.
On-demand courses include the full video presentation, downloadable slides, and additional resources mentioned in the Seminar Snapshot (Technical Corner, teach test, checklists).
Yes. You will have unlimited access to the course materials within the 1-year access period, so you can revisit the content anytime to refresh your knowledge.

Trusted by CPAs and Tax Professionals across Canada

This is a first time for me as well. Your firm was recommended to by one of my friends. Great source of information.

Thank you Mike, Hugh and team! I enjoyed the practical and realistic solutions to various tax issues.

Thank you ALL for such high quality courses and answering the questions in detail! So glad I found you guys!

Thank you very much for the seminars. They are very informative and helpful.

Thank you for the wonderful presentation, materials, and handling of queries as always.

This is my first time taking the Cadesky Tax Seminars. I am learning a lot and watching archived courses too. You have done a great job. Thank you so much!

I really enjoy your seminar series. Your presentations are extremely thorough and you explain complex tax issues very clearly.

The presentations are relevant. The material is easy to follow. Worked examples are excellent. It is a great value.