The pain of tax season is never really about April. It is about the eleven months before it, when receipts scattered as they arrived — into the glovebox, a junk drawer, three email accounts, a camera roll a thousand photos deep. Now the return is due, and you are searching for a year you barely remember, guessing at what you spent and hoping the paper turns up.
Dossier is an app built on the opposite habit: catch each document the moment it exists. Point your phone at the receipt in the parking lot, before you start the car. Dossier reads the payee, the date, the amount, and the tax, then shows you what it found. Tap "Looks good" and you can forget it. Ten seconds, and the receipt is saved, sorted, searchable, and filed under the line of your return where it belongs.
Keep that up all year and there is nothing left to reconstruct. No shoebox to empty, no statements to comb through, no expense you meant to write down in June. Your totals have been adding themselves up the whole time.
That is the trade: ten seconds now instead of a lost weekend in April. What it buys is a year that is finished when the year ends — and proof that still holds up if the Canada Revenue Agency (CRA) ever asks to see it.
What a claim is
Some spending is not taxed like the rest, on purpose. Childcare that lets you work, donations to charity, medical costs, the tools of a trade — Parliament decided those deserve a break. A claim is how you take it.
Claims come in two kinds, and the difference matters:
- A deduction shrinks your income before tax is worked out, so you are taxed on a smaller number. Childcare and RRSP contributions work this way.
- A credit shrinks the tax itself, after it is worked out. Donations and medical costs work this way. Most credits can take your tax down to zero but no further; a few pay out even when there is no tax left to shrink.
Earning money outside a paycheque works on the same principle. If you run a business or a side gig, Form T2125 gathers what came in and what it cost you, and sends one number to your return. If you rent out a property, Form T776 does the same for the rent and the expenses behind it. Every cost you subtract there is a claim too.
You do not need to keep any of this straight. Dossier includes a searchable guide with a page for every claim: what it is, what counts, and what the receipt has to show.
How long a receipt has to last
Here is the part that trips people up. When you file, the CRA takes your word for it. Nobody reads your receipts before the refund arrives, and a refund is not approval — it only means the numbers were accepted for now.
The questions come later, by mail, sometimes years after you filed. Most are routine reviews rather than audits: a letter asking to see what stands behind one line. Produce it and the matter closes. Come up empty and the claim comes off your return — you repay the tax, with interest, however real the expense was.
Keep every document that supports a claim for six years from the end of the tax year it relates to.
What happens at tax time
Dossier is not tax filing software. It sends nothing to the CRA and never decides a tax question. What it does is get the evidence and the arithmetic ready for whoever files — including you.
Filing yourself is the common case, in software such as Wealthsimple Tax or TurboTax. Open the Summary tab, where the year is already totalled line by line, and type the totals into the return. The figures are not guesses; every one traces back to a document you can produce.
Handing it off works the same way, with one more step. Export builds a single package: a summary whose totals add up, a spreadsheet with one row per document, and every original image. Give that to an accountant and the back-and-forth mostly disappears — the questions they would ask are already answered inside it.