How do I file years of back taxes I never filed?
Start with a map, not a return. Before anything is prepared, the years are listed with what was due in each: the return itself, any information returns, and whatever was due to another country. Each year is then marked with the position it is in — inside or outside the window for a refund, inside or outside the window in which it can still be assessed, covered or not covered by a disclosure route. That grid decides the order of filing. Prepared in the wrong order, the same set of returns can lose reliefs that were available at the start.
Will I get refunds from all those unfiled years?
Some of them, probably not all. The window for claiming a refund and the window in which a year can be assessed are not the same length, which produces the uncomfortable middle ground on these files: a year old enough that nothing can be paid back to you, but not old enough to be closed if it turns out you owe. That is mapped year by year first, because it changes what the exercise is for. Where some years are refund years and others are balance years, the order of filing affects the overall position.
Should I file all the years at once or one at a time?
In most cases together, as one package with one explanation. Relief is assessed on the whole picture: how the gap arose, when you realised, and what you did next. A single year filed on its own establishes facts about your knowledge that then have to be accounted for in every later submission. There are files where a particular year has to go first for a specific reason — a deadline falling soon, or a claim about to expire — but that is a deliberate decision taken from the map rather than the default way round.
Do I need to file information returns for the old years too?
Usually yes, and they are the part that gets forgotten. Information returns run on their own deadlines and carry their own consequences, separate from the return they accompany, so a year can be finished in the client's mind and still be incomplete. They also interact with the route: a disclosure route may cover one obligation and not another, which means coverage has to be checked obligation by obligation rather than year by year. Leaving them until after the returns are in is how a completed catch-up reopens.
Can the CRA come after me for years I never filed?
A year that was never filed does not quietly close the way a filed year does, which is why long gaps stay open and why exposure grows as years are added rather than ageing out of the picture. That is also the practical argument for acting before contact is made: the routes that improve a penalty position are generally more useful before an enquiry is raised than after it. What the gap actually costs depends on what sits behind it — tax, information returns, or neither — and that is established at the mapping stage.
What if I have no records for the earliest years?
It is normal, and it is not a reason to leave those years out. What survives is usually enough to build from: employment and bank records, records held by the authority itself, statements obtainable from institutions, and documents held by another country's administration. The returns are then prepared from reconstructed figures with the basis of the reconstruction documented, so a reviewer can see how each figure was reached. A gap in records is a fact to state in the narrative, not a hole to leave silent.
I work remotely from another country for a company back home — who taxes me?
Usually the country you are physically in, because employment income is generally sourced where the work is done, with your residence country taxing it as well if you are resident there and giving credit. Three things follow: your employer may acquire withholding and social security obligations where you sit, a treaty tie-breaker may be needed if both countries call you resident, and a short trip that becomes a long stay can cross a residence threshold nobody was watching. See remote workers and digital nomads.
Is double taxation illegal?
It is legal. Two countries can each have a valid claim on the same income — one because the income arose there, the other because you live there — and nothing prohibits both from exercising it. What exists instead is relief: tax treaties allocate the claim, and domestic law gives a credit for foreign tax paid. The relief is not automatic, though. It is claimed on a return, and unclaimed relief is simply lost. See how double taxation is relieved.
