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.
How does cross-border tax planning work?
It starts with facts rather than structures: which countries have a claim on you, what each one taxes, and where the two overlap. From there the decisions are about order and timing — which country taxes first, where relief is claimed, and whether a filing or a certificate has to be in place before money moves rather than after. Most of the value is in the sequencing, because relief claimed late is usually relief recovered slowly. See international tax planning.
How many days can I spend in a country before I become tax resident?
It depends on the country, and a day count is only ever the start. Many use a threshold in a tax year, some also look at averages across several years, and some have no day test at all and decide on where your home and life are. Two countries can both conclude you are resident, which is what the treaty tie-breaker exists to settle. Counting days without checking the tie-breaker is how people end up filing as resident nowhere. See the residency tie-breaker.
