ABSTRACT: The Heroes Earnings Assistance and Relief Tax Act of 2008 amended the anti‐avoidance provisions of the Internal Revenue Code for an expatriating taxpayer. The new law requires expatriating taxpayers to report a deemed taxable sale and repurchase of assets at the time that they expatriate. This is a change from the prior law where an expatriating taxpayer could be taxed by the U.S. for ten years after expatriation. The new U.S. rules are similar to rules that have been used by Canada to tax expatriating Canadian residents. This paper sets out the new U.S. rules and compares them to the Canadian departure tax. As can be seen, there are a number of similarities between the two countries' laws. However, there are also some major differences. The U.S. rules are more limited in application than the Canadian rules. As well as income tax, the U.S. legislators are concerned with estate and gift taxes, whereas the Canadian legislators are not.

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