Catch-Up Tax Filing Mississauga | Back Tax Returns & CRA Voluntary Disclosure

By Bader A. Chowdry, CPA, CA, LPA — AI Inventor & AI Specialist | Insight Accounting CPA Professional Corporation

Haven’t filed your taxes in years? You’re not alone — and we can fix it.

At Insight Accounting, we specialize in catch-up tax filing for individuals and businesses across Mississauga, Toronto, and the GTA who have fallen behind on their CRA obligations. Whether you have 1 unfiled year or 10, our experienced team will reconstruct your records, file your returns, and negotiate with CRA on your behalf.

We’ve seen everything. We fix it. No judgment.

📞 Call (905) 270-1873 for a confidential consultation.

What Is Catch-Up Tax Filing?

Catch-up tax filing means preparing and submitting tax returns for one or more years that were not filed by their original deadlines. This applies to:

Personal tax returns (T1) — individuals who haven’t filed for 1-10+ years
Corporate tax returns (T2) — businesses with unfiled annual returns
Trust returns (T3) — including the new bare trust reporting requirements
HST/GST returns — businesses with unremitted sales tax
Payroll remittances — employers behind on CPP, EI, and income tax withholdings
T4/T5 information returns — unfiled employer or investment slips

CRA Voluntary Disclosure Program (VDP)

The CRA’s Voluntary Disclosure Program allows taxpayers to come forward and correct their tax affairs before CRA contacts them. This can result in significant penalty relief.

How VDP Works:

1. Voluntary — you come forward before CRA initiates enforcement
2. Complete — all unreported income and unfiled returns must be disclosed
3. Penalty relief — partial or full waiver of penalties (interest still applies)
4. No prosecution — VDP applications accepted in good faith avoid criminal prosecution

Two VDP Tracks:

VDP Eligibility Requirements:

Disclosure must be voluntary (CRA hasn’t contacted you about it)
Must be complete (all years, all amounts)
Must include a penalty (at least 1 year late)
Information must be more than 1 year past due
Must include payment or acceptable payment arrangement

Our VDP success rate is exceptional. Bader Chowdry has successfully navigated dozens of VDP applications for clients in Mississauga, Toronto, and across Ontario.

CRA Penalties for Late Filing

Understanding the penalties helps you see why catching up NOW saves money:

Personal Tax (T1):

Late filing penalty: 5% of balance owing + 1% per month (max 12 months)
Repeat offenders: 10% + 2% per month (max 20 months)
Interest: Compounds daily at CRA prescribed rate

Corporate Tax (T2):

Late filing penalty: 5% of unpaid tax + 1% per month (max 12 months)
Failure to file: CRA can estimate your income and assess accordingly

HST/GST:

Late filing: 1% of net tax owing + 0.25% per month (max 12 months)
Repeat offenders: doubled penalties
Interest: daily compound on outstanding balances

Trust Returns (T3):

New bare trust rules: $2,500 penalty for late filing of Schedule 15
Bare trust deadline: March 31 annually
First-time filers often don’t realize they have an obligation

The longer you wait, the more it costs. Every day adds interest.

Common Scenarios We Handle

New Immigrants to Canada

Newcomers to Mississauga, Toronto, and Ontario often don’t realize they have Canadian tax obligations from their date of residency. We handle first-time filings, foreign income reporting (T1135), and treaty-based claims.

Cash-Based Businesses

Restaurants, retail stores, and service businesses in the GTA that operated primarily in cash often have gaps in records. Our Accounting Intelligence technology helps reconstruct income from bank deposits, third-party data, and industry benchmarks.

Deceased Estates

When a family member passes away, unfiled returns become the estate’s responsibility. We prepare final returns, optional returns, and clearance certificates to protect executors from personal liability.

Divorce & Separation

Tax filing often falls through the cracks during separation. We catch up both parties’ returns while optimizing for the changed filing status.

Business Transitions

Business owners who sold, closed, or restructured their business but never filed the final returns. We prepare all outstanding corporate, personal, and HST returns.

Freelancers & Gig Workers

Self-employed individuals in Toronto and Mississauga who didn’t realize they needed to file, or who fell behind. We reconstruct income from platforms, bank statements, and invoices.

Our Catch-Up Process

Step 1: Confidential Consultation (Free)

We review your situation, identify what’s unfiled, and assess your exposure. Everything is confidential under CPA professional privilege.

Step 2: Record Gathering & Reconstruction

We work with whatever records you have — bank statements, receipts, CRA My Account data, third-party slips. Our Accounting Intelligence technology helps fill gaps using pattern analysis and industry benchmarks.

Step 3: Return Preparation

We prepare all outstanding returns — T1, T2, T3, HST, T4, T5 — ensuring accuracy and maximizing legitimate deductions even for past years.

Step 4: CRA Strategy & Filing

Before filing, we develop a strategy:

Should we apply for VDP?
Can we request taxpayer relief for penalties?
What payment arrangement is realistic?
Are there statute-barred years we can leverage?

Step 5: CRA Negotiation

We communicate directly with CRA on your behalf:

Penalty and interest relief requests
Payment plan arrangements
Objections to arbitrary assessments
Resolution of garnishments or legal actions

AI-Powered Document Reconstruction

When records are missing or incomplete, our Accounting Intelligence technology helps:

Bank statement analysis — categorize thousands of transactions automatically
Income reconstruction — cross-reference deposits against industry patterns
Expense estimation — apply CRA-accepted benchmarks for missing receipts
Multi-year pattern detection — identify trends across unfiled years
CRA data matching — reconcile against T-slips and third-party information on file

This means faster, more accurate catch-up filings — even when records are incomplete.

AI-Powered Catch-Up Filing

At Insight Accounting CPA Professional Corporation, we understand that catching up on years of unfiled tax returns can feel overwhelming—especially when records are incomplete or missing entirely. Our proprietary Accounting Intelligence platform transforms this daunting process through AI-powered reconstruction capabilities that can piece together your tax history even when documentation is scarce.

Automated Historical Transaction Reconstruction from Bank Feeds

When years of bookkeeping have been neglected, our AI systems can analyze bank and credit card statements to reconstruct income and expense categories automatically. The platform recognizes transaction patterns, identifies recurring expenses, classifies deposits by source, and applies machine learning to categorize thousands of transactions that would take weeks to process manually. For Mississauga and GTA businesses with multiple accounts and years of missing records, this automated reconstruction provides the foundation for accurate catch-up filings without the prohibitive cost of manual data entry.

AI-Driven Document Matching Across Multiple Tax Years

Catch-up filing often involves coordinating information across multiple tax years—T4 slips received in different years, carry-forward amounts from previous returns, and accumulated capital losses. Our AI platform organizes documents by tax year, matches slips to the appropriate returns, identifies missing information that CRA may have on file, and calculates available carry-forwards including RRSP room, capital losses, and non-capital losses. This systematic cross-year analysis ensures that each return maximizes available claims while properly accounting for amounts carried forward from prior years.

Intelligent Penalty and Interest Estimation with CRA Voluntary Disclosure Analysis

Understanding the financial exposure from unfiled returns is critical for deciding whether to pursue the Voluntary Disclosure Program (VDP). Our AI systems calculate estimated penalties and interest for each unfiled year, comparing the costs of voluntary disclosure against the potential costs if CRA discovers the non-compliance first. The platform models different VDP scenarios—General vs. Limited track—and projects the potential savings from penalty relief and interest reductions. This quantitative analysis helps clients make informed decisions about disclosure strategy based on hard numbers rather than speculation.

Automated Prioritization of Filing Years for Maximum Refund Recovery

When catching up on multiple years, the order of filing can affect your financial outcome. CRA allows refunds to be claimed for returns filed within three years of the original due date, but some credits and carry-forwards have different limitation periods. Our AI platform analyzes your situation to prioritize filing years that preserve refund entitlements, maximize available credits, and optimize the sequence for claiming carry-back elections. For GTA residents who may be owed refunds from some years while owing taxes in others, this strategic prioritization ensures you don’t leave money on the table.

AI-Enhanced Negotiation Support for CRA Payment Arrangements

When catch-up filings result in significant balances owing, negotiating reasonable payment arrangements with CRA is essential. Our AI systems analyze your financial capacity, project sustainable payment schedules, and prepare comprehensive financial disclosures that support requests for relief. The platform identifies applicable taxpayer relief provisions, tracks changing CRA policies on penalty and interest abatement, and prepares the documentation required to support your case. This systematic approach improves outcomes when seeking penalty relief or negotiating manageable payment terms.

Ready to get back on track with AI-powered catch-up filing? Explore our AI & Automation services or contact us for a confidential consultation about your unfiled returns.

Frequently Asked Questions

How far back can CRA go for unfiled returns?

There is no limitation period for unfiled returns. CRA can assess you for any year you haven’t filed. However, for filed returns, CRA generally has 3 years (normal reassessment period) or 6 years if they suspect negligence.

Will I go to jail for not filing taxes?

Tax evasion (deliberately hiding income) can result in prosecution. However, simply falling behind on filing — especially if you come forward voluntarily — almost never results in criminal charges. The VDP specifically protects against prosecution.

Can you help if CRA has already contacted me?

Yes, but VDP may no longer be available for the specific items CRA has raised. We can still file your returns, negotiate penalties, and represent you in CRA proceedings. The sooner you act, the more options we have.

What if I don’t have any records?

We can work with bank statements, CRA My Account data (T-slips), and third-party information to reconstruct your returns. Our AI technology helps fill gaps. Something is always better than nothing.

How much does catch-up filing cost?

Fees depend on the number of unfiled years, complexity, and record availability. Simple personal catch-ups start at competitive rates per year. Complex corporate or multi-year situations are quoted based on scope. Call (905) 270-1873 for a free assessment.

Can I get my refunds for past years?

Yes — if you’re owed a refund, you can claim it by filing within 10 years of the original due date. Many of our GTA clients discover they’re actually owed money from past years.

Book Your Confidential Consultation

Insight Accounting CPA Professional Corporation
📍 4300 Village Centre Ct, Unit 100, Mississauga, ON L4Z 1S2
📞 (905) 270-1873
📧 info@insightscpa.ca
🌐 insightscpa.ca

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