6 worked Stock and Securities Tax Reporting case studies — the position a client typically comes to us with, what we do, and what it is worth. Each is an illustrative example built on the rules that apply to stock and securities tax reporting work, not a specific client's file.
Case Study 1 · Scaling without breaking
Growth Handled Without A Missed Filing, $146,000 Freed — Student Filer, Winnipeg
Client: A full-time student with tuition credits and part-time earnings · Where: Winnipeg, Manitoba · Engagement: 6 weeks, fixed fee
Cash freed$146,000
Compliance failuresNone
ReportingMonthly
The situation — A full-time student with tuition credits and part-time earnings, Winnipeg, Manitoba
A full-time student with tuition credits and part-time earnings in Winnipeg, Manitoba was opening in a second province. That meant different filing obligations and a different payroll regime. Foreign accounts that had crossed the T1135 threshold two years earlier already sat in the file.
What we did for A full-time student with tuition credits and part-time earnings, Winnipeg, Manitoba
We reported the disposition and filed the principal residence designation for the year of sale, closing the late-designation exposure before the CRA raised it. We then put monthly reporting in place. That let the owner see the cash effect of growth while there was still time to act on it.
The result — A full-time student with tuition credits and part-time earnings, Winnipeg, Manitoba
Growth was absorbed without a compliance failure. $146,000 of cash was released, and the monthly reporting now flags a problem while it is still small.
Case Study 2 · Deadline rescue
6-Week Turnaround Beat The Deadline And Saved $76,000 — US-Dividend Investor, Hamilton
Client: A taxpayer with US-source dividends · Where: Hamilton, Ontario · Engagement: 6 weeks, fixed fee
Late-filing penalty avoided$76,000
Filed with20 days to spare
Next yearPapers ready
The situation — A taxpayer with US-source dividends, Hamilton, Ontario
A taxpayer with US-source dividends in Hamilton, Ontario was weeks away from the deadline for stock and securities tax reporting. Behind that sat years of small donation receipts claimed one at a time instead of pooled onto a single return. The exposure if the date slipped was around $76,000.
What we did for A taxpayer with US-source dividends, Hamilton, Ontario
We pulled the full slip history from the CRA record, refiled the affected years by adjustment request, and recovered the credits that had been missed. The filing went in complete rather than provisional, so there was no amended return to follow.
The result — A taxpayer with US-source dividends, Hamilton, Ontario
Filed with 20 days to spare. $76,000 in late-filing penalties avoided, and the working papers are ready for the following year.
Case Study 3 · Objection and relief
$94,000 Of Penalties And Interest Cancelled On Relief — First-Year Physician, Surrey
Client: A physician in their first year of practice · Where: Surrey, British Columbia · Engagement: 3 weeks, fixed fee
Penalties and interest cancelled$94,000
Relief groundsAccepted
AssessmentAdjusted to filed position
The situation — A physician in their first year of practice, Surrey, British Columbia
An assessment of $94,000 landed at a physician in their first year of practice in Surrey, British Columbia following a desk review. It turned on three years of returns filed without the slips that had been mailed to an old address. The auditor had not seen the records behind it.
What we did for A physician in their first year of practice, Surrey, British Columbia
We pooled the carried-forward donation receipts onto the higher-income spouse’s return so the whole claim sat above the low-rate first tier. We then set out the legislative basis for the position alongside the documents supporting it.
The result — A physician in their first year of practice, Surrey, British Columbia
$94,000 of penalties and interest was cancelled under the taxpayer relief provisions, and the underlying assessment was adjusted to match the filed position.
Case Study 4 · Planning that cut the bill
$27,500 Cut From The Annual Tax Bill — Gig-Economy Driver, Halifax
Client: A gig-economy driver · Where: Halifax, Nova Scotia · Engagement: 7 weeks, fixed fee
First-year saving$27,500
RepeatsAnnually
Filing positionUnchanged in risk
The situation — A gig-economy driver, Halifax, Nova Scotia
A gig-economy driver in Halifax, Nova Scotia was compliant but paying more than it needed to. The prior year had been filed correctly. It still left a rental property reported without any capital cost allowance analysis on the table.
What we did for A gig-economy driver, Halifax, Nova Scotia
We modelled the current position against the alternatives before changing anything. Then we reset the medical expense claim window, transferred credits between spouses, and applied the tuition and disability amounts to the return that used them.
The result — A gig-economy driver, Halifax, Nova Scotia
The change saved $27,500 in the first year and repeats annually. Nothing about the filings became more aggressive. The position is simply the one the rules already allowed.
Client: An employee with foreign investment accounts · Where: Saskatoon, Saskatchewan · Engagement: 5 weeks, fixed fee
Overpayment refunded$119,000
Late remittances sinceZero
ScheduleAutomated
The situation — An employee with foreign investment accounts, Saskatoon, Saskatchewan
Remittances at an employee with foreign investment accounts in Saskatoon, Saskatchewan were consistently late by a few days. That was enough to trigger penalties every quarter. Behind it sat a home sale never reported on the basis that the gain was exempt anyway.
What we did for An employee with foreign investment accounts, Saskatoon, Saskatchewan
We obtained the signed T2200 and rebuilt the employment-expense claim on the prescribed form with the supporting records attached to the file. Then we moved the remittance dates into a scheduled process rather than a monthly decision.
The result — An employee with foreign investment accounts, Saskatoon, Saskatchewan
Penalties stopped from the following remittance onwards, and $119,000 of overpaid instalments was refunded.
Case Study 6 · Missed incentive claimed
Incentive Review Recovered $110,000 Across 3 Open Years — First-Time Home Buyer, London
Client: A first-time home buyer · Where: London, Ontario · Engagement: 5 weeks, fixed fee
Recovered$110,000
Open years claimed3
Ongoing trackingIn place
The situation — A first-time home buyer, London, Ontario
An incentive review at a first-time home buyer in London, Ontario started from a simple question: what has never been claimed? The answer ran to 3 years. It was driven by employment expenses claimed with no signed T2200 from the employer to support them.
What we did for A first-time home buyer, London, Ontario
We carried the capital loss back against gains reported in the prior three years and generated a refund rather than a carry-forward balance. We documented eligibility to the standard a reviewer would apply rather than the standard a claim form requires.
The result — A first-time home buyer, London, Ontario
The credits produced $110,000 across the open years. The tracking now in place means the following year's claim is documented as the work happens rather than reconstructed afterwards.
Reviewed by Udit Gupta, Founder and Tax Accountant for the 2025 tax year. These case studies are illustrative worked examples composed from the CRA rules that apply to this type of work, not specific client files; figures are representative and outcomes depend on your own facts.
