Post-mortem planning & pipeline — can I handle this myself?
Some of it, yes — and we will say so on the call if that is the honest answer. The parts that are worth paying for are the ones where a missed election, a missed deadline or an unverified threshold costs more than the fee: pipeline and redemption strategies address that double inclusion within defined timeframes, and each interacts differently with a foreign estate tax and foreign beneficiaries.
What if I have already filed and got it wrong?
That is a common starting point. We re-derive the position, identify whether an amendment or a disclosure route is the right vehicle, and tell you which one preserves the relief that is still available. The order matters more than the speed.
How long will it take?
It depends on the documents rather than on us. Once the pack is complete most filings turn around inside a fortnight; anything that needs a certificate from a tax authority runs on that authority's timetable, which we tell you at the start rather than at the end.
Why is my parent's company taxed twice when they die?
Because two separate events can capture the same value. On death there is a deemed disposition of the shares, which brings the accrued gain into the deceased's final return. The company then has to get that value out to the estate, and the distribution is itself taxable in the hands of the estate or the beneficiaries. Nothing has been received twice, but tax has been charged twice on the same underlying amount. Post-mortem planning exists to address that double inclusion, and the routes available depend on what the company holds, who the beneficiaries are and where they live.
What is a pipeline and how is it different from a redemption?
They are two different ways of getting value out of a company after a shareholder has died, and they produce different characters of income. Broadly, a redemption route works with the dividend treatment that arises when the company buys back its shares, and relies on relief that matches that dividend against the loss the estate realises. A pipeline instead preserves the cost base created by the deemed disposition at death, so value comes out as a return of capital over a period rather than as a dividend. Which one fits depends on the assets, the beneficiaries and the time available, and the two are not always alternatives.
How long after death do we have to decide?
Long enough to think, and not long enough to drift. The routes that address this double taxation operate within defined timeframes measured from the date of death, and once a window has passed the option behind it is simply gone — there is no application to reopen it. That is why the value in this work sits at the beginning, while the estate is still gathering documents, rather than at the end when returns are being prepared. Raise the question early, even if the answer is that nothing needs to be done yet. A representative who waits until the estate's first return is due has often lost the choice.
Does a pipeline still work if the beneficiaries live in the United States?
It can, but their position has to be part of the decision rather than an afterthought. A route that is efficient in Canada can produce an awkward characterisation abroad, because the other country decides for itself whether what the beneficiary receives is a dividend, a distribution of capital or something else, and whether the relief they need is available to them. A foreign estate tax may also apply to the same assets on its own rules and its own timetable. The analysis has to be run in both countries at once, and the plan chosen on the combined answer rather than on the Canadian answer alone.
Can we do post-mortem planning if the company owns real estate?
What the company holds changes the analysis considerably. A company whose value sits in real property, one holding a portfolio of investments, and one carrying on an operating business each behave differently — for the availability of the routes, for the practical steps involved, and for the cost of unwinding afterwards. Property in another country adds a further layer, because that country may tax the transfer or the eventual sale on its own rules. The honest answer is that the route cannot be chosen from the share certificate alone. The financial statements, the asset list and the shareholdings have to be read first.
The executor has already distributed — is it too late to plan?
It depends on what was distributed and from where. If the estate has paid out cash it happened to hold, the shares may still sit in the estate and the position may still be open. If the company has already been wound up, or the shares transferred to beneficiaries personally, several routes will have closed. The first task in that situation is to establish exactly what has been done and when, from the corporate records and the estate accounts, before any advice is given. Some of what remains can still be improved; some of it cannot, and saying so plainly is part of the job.
Is double taxation legal?
Yes. Nothing prevents two countries from taxing the same income under their own domestic law — each is exercising its own jurisdiction. What treaties and credit systems do is relieve the outcome rather than prohibit the charge, and relief is generally something you must claim on a return or a form, not something applied automatically. Miss the claim and the double charge stands. Double taxation explains the mechanism.
Do Canada and the United States share tax information?
Yes, through more than one channel. The treaty has an exchange-of-information article that supports both routine and on-request exchange. Separately, an intergovernmental agreement has Canadian financial institutions identify US-reportable accounts and report them to the CRA, which passes them to the IRS, with the reverse flow for Canadian residents. Most other country pairs use the Common Reporting Standard for the same purpose. See FATCA reporting.
