Insolvency and Restructuring Tax Support Case Studies
6 worked Insolvency and Restructuring Tax Support 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 insolvency and restructuring tax support work, not a specific client's file.
Case Study 1 · Planning that cut the bill
Remuneration Review Saved $52,000 Across Corporate And Personal Returns — Employer Under Payroll Review, Windsor
Client: A company facing a payroll trust examination · Where: Windsor, Ontario · Engagement: 5 weeks, fixed fee
Combined saving$52,000
ScopeCorporate + personal
Future yearsNo rework needed
The situation — A company facing a payroll trust examination, Windsor, Ontario
Nothing was wrong at a company facing a payroll trust examination in Windsor, Ontario — the filings were on time and accurate. What they were not was planned. A proposal letter with a 30-day response window and no supporting records assembled had never been reviewed.
What we did for A company facing a payroll trust examination, Windsor, Ontario
We assembled the contemporaneous records, filed a structured response to each proposed adjustment with the supporting documents indexed, and had the proposal withdrawn, and ran the numbers across both the corporate and personal returns so the saving was real rather than deferred into someone else's hands.
The result — A company facing a payroll trust examination, Windsor, Ontario
$52,000 came off the combined corporate and personal tax bill, and the structure holds for future years without further work.
Case Study 2 · Deadline rescue
Filed On Time From A Standing Start, $117,000 Penalty Avoided — Taxpayer Facing Collections, Lethbridge
Client: A taxpayer with frozen bank accounts · Where: Lethbridge, Alberta · Engagement: 10 weeks, fixed fee
Penalty avoided$117,000
Turnaround10 weeks
FiledOn time
The situation — A taxpayer with frozen bank accounts, Lethbridge, Alberta
A taxpayer with frozen bank accounts in Lethbridge, Alberta came to us 10 weeks before its filing deadline with a waiver signed at the counter that kept an otherwise closed year open with no end date. A late filing would have triggered a penalty of roughly $117,000 before interest.
What we did for A taxpayer with frozen bank accounts, Lethbridge, Alberta
We worked backwards from the deadline. We requested the auditor’s working papers and report to see how the assessment had been built before answering any of it, prioritising the items that actually gated the filing and deferring everything that did not.
The result — A taxpayer with frozen bank accounts, Lethbridge, Alberta
The return was filed on time and complete. The $117,000 penalty never arose, and the compliance calendar we set means the next deadline is scheduled rather than discovered.
Case Study 3 · Backlog brought current
Collections Halted And $141,000 Cut From A 3-Year Backlog — Family Business Under Review, Edmonton
Client: A family business under a related-party review · Where: Edmonton, Alberta · Engagement: 6 weeks, fixed fee
Balance reduced by$141,000
Backlog cleared3 years
CollectionsHalted
The situation — A family business under a related-party review, Edmonton, Alberta
By the time a family business under a related-party review in Edmonton, Alberta called, 3 years were outstanding and the CRA had assessed on estimates. Underneath it sat a net-worth assessment built on unexplained deposits that were actually loan proceeds.
What we did for A family business under a related-party review, Edmonton, Alberta
We reconstructed the records year by year and filed the Tax Court appeal inside the window and resolved the remaining adjustments before a hearing date was needed. Each filing replaced an arbitrary assessment with a real one.
The result — A family business under a related-party review, Edmonton, Alberta
The account is current. Filing on real numbers rather than CRA estimates reduced the balance by $141,000, and a relief application addressed part of the accumulated interest.
Case Study 4 · CRA review defended
Audit Defence Closed In 4 Weeks, $115,000 Cleared — Importer Under Audit, Halifax
Client: An importer under a customs and GST audit · Where: Halifax, Nova Scotia · Engagement: 4 weeks, fixed fee
Proposed tax cleared$115,000
Review duration4 weeks
OutcomeNo change
The situation — An importer under a customs and GST audit, Halifax, Nova Scotia
An importer under a customs and GST audit in Halifax, Nova Scotia was selected for review after a confirmation letter left in a drawer until the appeal window had closed showed up in the CRA's automated matching. The proposed adjustment on insolvency and restructuring tax support came to $115,000.
What we did for An importer under a customs and GST audit, Halifax, Nova Scotia
We kept the waiver narrowed to the issue actually under review and let the remaining years close on the normal reassessment period. Every figure in the response traced to a source record the auditor could verify without asking a second question.
The result — An importer under a customs and GST audit, Halifax, Nova Scotia
The review closed with no change. $115,000 of proposed tax came off the table, and the documentation now in place makes the next review a short one.
Case Study 5 · Cash and remittance control
$21,000 Of Working Capital Freed From The Tax Cycle — Late-Objection Taxpayer, Regina
Client: A taxpayer whose objection window has closed · Where: Regina, Saskatchewan · Engagement: 6 weeks, fixed fee
Working capital freed$21,000
On-time remittancesEvery period since
Forecast horizon13 weeks
The situation — A taxpayer whose objection window has closed, Regina, Saskatchewan
A taxpayer whose objection window has closed in Regina, Saskatchewan was profitable on paper and short of cash every month. An objection deadline that had passed with no extension applied for explained most of the gap.
What we did for A taxpayer whose objection window has closed, Regina, Saskatchewan
We answered each query in writing with an indexed document package, so the file showed exactly what the auditor had received and on what date and built a thirteen-week cash view so tax payments stopped competing with payroll for the same dollars.
The result — A taxpayer whose objection window has closed, Regina, Saskatchewan
$21,000 was released back into working capital. Remittances have been on time every period since, and the forecast shows the tax outflow before it lands.
Case Study 6 · Objection and relief
Notice Of Objection Allowed In Full, $80,000 Reversed — Voluntary Disclosure Applicant, Moncton
Client: A business owner considering a voluntary disclosure · Where: Moncton, New Brunswick · Engagement: 8 weeks, fixed fee
Amount reversed$80,000
ObjectionAllowed in full
Account balanceNil
The situation — A business owner considering a voluntary disclosure, Moncton, New Brunswick
A business owner considering a voluntary disclosure in Moncton, New Brunswick had been reassessed for $80,000 and had 17 days left on the objection deadline. The reassessment rested on six years of unfiled corporate and personal returns and an active collections file.
What we did for A business owner considering a voluntary disclosure, Moncton, New Brunswick
We filed the objection inside the deadline with a complete submission rather than a placeholder, and filed the disclosure through the Voluntary Disclosures Program before contact, which removed the gross-negligence penalty entirely.
The result — A business owner considering a voluntary disclosure, Moncton, New Brunswick
The appeals officer allowed the objection in full. $80,000 was reversed and the account returned to a nil balance.
Reviewed for the 2025 tax year by Udit Gupta, Founder and Tax Accountant. 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.
