Tax Issues

Total 358 Posts

Canadians Beware – U.S. Move To End Paper Cheques for Federal Payments

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On March 25th, 2025, President Donald Trump issued Executive Order 4247 (“EO 4247”) directing the U.S. Department of the Treasury to transition all federal disbursements and collections into electronic format; effectively ending the use of paper cheques. By September 30th, 2025, paper cheques for federal payments (notably tax refunds and social security payments) will cease. How is this relevant to Canadians? Hurdle for Canadians EO 4247 may represent a hurdle….

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IRS, Tax Issues, U.S. Citizen, United States, US Taxes

Taxation of Employee Stock Options on Death

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In Canada, it is not uncommon for employers to grant stock options to employees as a form of compensation, notably in technology and startup sectors. These stock options provide employees the right to purchase company stocks at a predetermined price, often referred to as the “exercise price.” What are the tax implications of these stock options when the employee dies while holding unexercised stock options? The tax treatment on death….

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Succession Planning, Tax Issues, US Taxes, valuation

Clarifying U.S. Estate Tax for Canadians

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It comes as a surprise to many Canadians to learn their estate may be subject to U.S. estate tax. Indeed, the U.S. estate tax regime is broad and complex and misunderstood by many Canadians. This article will provide a summary overview of its application to Canadian and how to minimize its implications. U.S. Estate Tax Regime in General All U.S. persons (U.S. citizen, U.S. resident or green card holder) are….

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Canadian and US Tax Treaty, Estate Planning, International, IRS, Tax Issues, US Taxes

The Limits of Pour-Over Clauses in Ontario (And What to Do Instead)

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    Today’s blog was written by Karen La Caprara, Counsel, at Fasken LLP. Pour-over clauses in wills are a staple in U.S. estate planning, used to direct estate assets into an existing trust. But in Ontario and British Columbia, these clauses can lead to invalid testamentary gifts, intestacy, and costly litigation. What Is a Pour-Over Clause—and Why Is It Problematic? A pour-over clause is a provision in a will that….

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Estate Administration, Estate Planning, Succession Planning, Tax Issues, Trusts, United States, Wills

Cross-Border Charitable Donation & U.S. Donor

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Philanthropy can strengthen one’s estate plan. In Canada, an estate plan may integrate charitable donations to leave a legacy to our community while taking advantage of the associated tax benefits. Such strategy can be implemented during the donor’s lifetime or upon the donor’s death. If the donor is a U.S. citizen living in Canada (hereinafter referred as a “U.S. donor”), does the strategy work? U.S. donor & U.S. Tax Filings….

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Charitable Giving, International, Philanthropy/Charitable Giving, Tax Issues, U.S. Citizen, US Taxes

Ontario Estate Information Return Essentials

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  The Institute of Law Clerks of Ontario recently hosted an education session on Ontario’s Estate Administration Tax (“EAT”) and the Estate Information Return (“EIR”), presented by a representative of the Ontario Ministry of Finance (“MOF”). I was particularly interested in this session as I wrote about the new online filing process for EIRs in my last blog post https://allaboutestates.ca/estate-information-return-the-new-online-process/. Today’s blog will share some of the key takeaways from….

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Estate Administration, Estate Administration and Probate Applications, Estate Planning, Probate Tax, Tax Issues, Wills
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