r/cantax • • 17h ago

Ontario small business- not filed taxes for the last ten years and have outstanding GST/HST.

3 Upvotes

We are helping my brother get back on track. What concerns me is that he has not filed his taxes, and he’s been receiving letters from the CRA indicating that he owes outstanding GST/HST.

What happens if he doesn’t have the money to pay back the CRA? Can he file for bankruptcy? Can they go after his home or his vehicle to recover the money?

I want to hire a bookkeeper, but he doesn’t have the money to pay one. We family members don’t know what to do. If we lend him the money, we will probably never see a dime back. But if we ignore the letters, we don’t know what will happen if he continues not filing or responding to the CRA.

Does anyone have experience with something like this? Are there any bookkeepers who do pro bono work or offer subsidized services?
My brother is in denial, but a lot of this has to do with the heavy medication he’s been on since being diagnosed with extreme bipolar disorder in 2019. I feel bad for him, and I know he has some responsibility for the situation, but what can we do to help?

He continues to run his business mostly from his bedroom since the meds he’s on make him drowsy and unstable. He’s got employees but I’m worried they are taking advantage of him.


r/cantax • • 14h ago

Seeking advice - sunbroker taking over insurance firm

0 Upvotes

Hello all - hoping for some guidance, I have been the succession plan for my small Ontario corporation focusing on life insurance for a few years now. Principal is ready to make the transition but I'm feeling a bit unprepared and nervous from the tax side of things. He has done his own bookkeeping and a few things on the financials concern me.

If anyone is familiar with the industry and independent firm operations would love some input. Here are my main questions:

  1. Is it normal to transfer ownership of an existing Corp or should I open a new Corp and transfer assets / clientele? There is a brand established and paper trail as the firm been in operations about 20 years.
  2. How does one go about finding an accountant for this specific stage of business transition?
  3. I am concerned about inheriting tax liability as the principal did his own bookkeeping, what are some ways to protect myself?

r/cantax • • 1d ago

Attribution confusion

4 Upvotes

My parents are in the process of selling a vacation property. My father bought it in the 1960s, then married a few years later. My mother was added to the title shortly after they were married.

Is it correct to say that my father owes 100% of the tax on the property because he provided the original capital? It seems strange because they've jointly owned it for 50 years. Has anyone been able to successfully argue with CRA that the tax burden should be shared, given that she equally contributed to property improvements, maintenance, insurance, utilities, property tax, etc for such a long period of time?

If it matters, they separated a few years ago but don't have a separation agreement. They have another property that is more suitable for the principle residence exemption. And they did file the T664 form in 1994.


r/cantax • • 1d ago

What are the downsides of owning private company stock through a holding corporation?

0 Upvotes

I'm planning the ownership structure for my shares in a US startup that I co-founded. I'm aware of the maintenance costs of filing the holdco tax returns. My goal is to be able to operate with pre-personal tax income, for example, investing in/starting another business or buying investment properties. Other than that, I'm not planning to run an active business through this corporation.

If you've had a similar setup, what gotchas did you discover throughout the process?


r/cantax • • 1d ago

How can I fill out form T2209? Which numbers do I pull from my US W-2?

1 Upvotes

I received a review letter from the CRA regarding the foreign tax credit I claimed on my 2025 T1 return. I worked in the US in 2025, and I want to make sure I am filling the form properly. For line 43100, I calculated the taxes paid to the US as follows (Federal + State + FICA - refunds). And for line 43300, I calculated my US income from my W-2 as Box 1 (wages, tips, other comp.) + Box 12b (contributions to a retirement plan). Are these the correct calculations for lines 43100 and 43300? Please note I am a factual resident of Canada, as my family still resides in Canada and I travel back and forth every 2 weeks.


r/cantax • • 1d ago

Winding up CCPC with a loss

4 Upvotes

Hi there, looking for opinions on a situation. CCPC (sole shareholder) bought an e-commerce business (arms-length) in 2025, that lost money, ceased operations this year. Corp has no assets or liabilities (operating losses were covered by shareholder). Considering dissolving entity but want to confirm path to shareholder getting tax benefit (ABIL ideally).

For ABIL, looking at deemed disposition rules, how important is it that the corp have liabilities? If no assets and no liabilities, is that sufficient or do there need to be liabilities the corp cannot meet?

If I go ahead and dissolve the corp this year, does that impact potential for ABIL?

Any scenario where the above would give rise to capital loss for the shareholder vs ABIL?


r/cantax • • 1d ago

AI for tax

0 Upvotes

What are some actual good tax AI softwares that everyone uses and don't cost too much


r/cantax • • 2d ago

Ebay and future tax season

1 Upvotes

Hello,

I've been selling off my vintage video game collection on Ebay over the last month or so, and have started dabbling in video game flipping, as I realized I enjoyed the selling process. My net total sales is currently over $3,000 and I still have some of my collection to sell.

My question is, does this qualify me as a small business and the T2125? I've only bought two games off Ebay so far with the intention to re-sell, the rest is 20+ year old stuff. I haven't sold any newly bought games and none of my orders sold have been more than $700. The Ebay buyers have all been American, if that's important.

I obviously don't have records of the original purchases of the old games, most were parental gifts as a kid/teen.


r/cantax • • 3d ago

What steps to take if I need to take a loan from my corporation for just 10 days and return it after?

3 Upvotes

Situation:

I need $800K deposited into an account before October 31st to take advantage of a 2% transfer-in promo (BMO).

I have the funds personally but they were locked in a "Notice Savings Account," and the funds will become available on October 25th to transfer out. This is cutting it very close to the deadline.

I have the funds "free" in my corporation. Can I take the 800K from my corp today and return it in the next 1 to 2 weeks or do I need any special considerations for this?

I looked online and everything says documenting it and paying your corporation interest but most of those things online are for long term loans. Do I still need to pay my corporation interest for just 1 to 2 weeks of taking the money? I don't want to risk getting flagged/audited by the CRA. Thanks!


r/cantax • • 3d ago

question on tax-paying timing in retirement

0 Upvotes

My wife and I are newly retired this year. For 2026, our taxes will include a bunch of tax withholding from our regular jobs, but of course 2027 will be the first year we're going to have no employment income--only pension income, capital gains from non-registered investment account drawdown, and some money from drawing down our RRSP/RRIF investment account. And eventually we'll have CPP and OAS.

We'd like to avoid doing the CRA quarterly installment thing, so I have a question about the timing of paying taxes owed. Ideally, we would of course like to keep as much money in our own pocket (translation: be able to invest it and grow it) for as long as possible during each year.

So, my question is this: In mid-December every year, am I allowed to simply calculate whatever tax we have incurred for the year, subtract whatever tax was already withheld from pensions, CPP, OAS, etc, and then make a single late-December payment to CRA to pay off the remainder of what we will owe for that year's taxes? Or, if I do that, will CRA come back and say "you needed to be paying us throughout the year whenever there was a taxable event; so despite the fact you fully paid your taxes for this year in December ahead of April when they're due, we're going to put you on quarterly installments anyway"?


r/cantax • • 4d ago

Dividend vs Bonus

0 Upvotes

2025 was the first year of my friends corp. He incorporated and didn’t tell me until it was almost time to file his year end. Didn’t even have a corp bank account. So he took all his corp earnings into his personal account. He also had very little expenses. I told him he has to repay that money, and he never did. Fast forward to this year and he still hasn’t repaid it. Shareholder loan has a debit balance from last year in addition to this year, but he did open a corp bank account and transfer some money in but not much. So he’s potentially facing a large dividend this year to clear out two years of draws. I’m not sure if it makes sense to retroactively declare a dividend for 2025 and then adjust both the T2 and his T1, with penalties, interest etc. Or just face a large one this year with no penalties or interest yet


r/cantax • • 3d ago

Best way to dispose of Around 250 grams of 24 carat gold in Pamp bars

0 Upvotes

I've been buying gold in smaller pamp bars (most are 10 grams) and when entering Canada I declared them in my goods to follow. I'm now thinking of selling them gradually and putting the money in TFSA. I understand that there might be capital gains, so what's the best way to deal with this knowing that I can sell them gradually over time.

Cheers.


r/cantax • • 4d ago

Long-term investing during a temporary 1–2 year stay in Canada before returning to Spain

1 Upvotes

Hi everyone,

I recently moved to Canada and expect to return to Spain in about 1–2 years. My investment horizon is 10–20 years, so I won't need to cash out when I leave.

I already hold European accumulating UCITS index funds purchased before becoming a Canadian tax resident. I'm trying to decide how to handle new investments during my stay: continue contributing to those funds, or use a Canadian brokerage to buy broadly diversified ETFs.

I'm looking for guidance on the overall approach rather than recommendations for specific securities. My main concerns are Canadian taxation of foreign accumulating funds, departure tax, brokerage restrictions after moving, and potentially being taxed again when eventually selling in Spain.

For someone in this situation, what factors would you consider when choosing where and how to invest? Would selling before leaving simplify things, or could keeping the investments and transferring them in kind be practical?

I'd appreciate experiences from anyone who has moved from Canada back to Spain, as well as suggestions on what to clarify with a cross-border tax adviser.

Thanks!


r/cantax • • 4d ago

Fixing "Unused Contributions" after RRSP over contribution a couple years ago

2 Upvotes

In tax year 2023 I accidentally over contributed to my RRSP. Basically, I made a lump-sum contribution in July 2023 -- somehow forgot about it -- and then made the same lump sum contribution in January 2024. I noticed the mistake when I worked on my taxes in April 2024.

I immediately withdrew the overage from my RRSP account. I did not bother trying for a tax deduction waiver. I did file asking for a waiver asking to waive penalties and interest which was granted since the mistake was reported immediately and only 3 months had past.

In 2025 I filled out the T1 OVP and everything was accepted and approved and done. Or so I hoped...

I noticed when filing my 2025 taxes that my CRA account is still carrying extra "Unused RRSP contributions" balance to the amount that I withdrew from the RRSP. I had hoped that the T1 OVP was going to fix all that, but here we are in October and the amount is still (AFAICT) incorrect.

If my searching is correct, I see that maybe I need to file a T746. I have looked at that form for a couple hours and am completely lost since the wording on the form implies it much with my 2024 filing with T4RSP income, but I've already filed the 2024 taxes and reported the t4rsp.

It feels to me that everything is correct except CRA needs to deduct the T4RSP amount from the "Unused Contributions" count and I just can't wrap my head around how filling out a T746 isn't going to lead me down some dark path of creating an even bigger mess. If anyone has suggestions on if I'm missing something, or need to figure out this t746, please holler.


r/cantax • • 5d ago

Can I claim medical/dental expenses for previous years?

1 Upvotes

If I refile my taxes using the mail in service can I claim medical/dental expenses for previous years?


r/cantax • • 5d ago

ETF eligibility for interest deduction

0 Upvotes

I have a question in regards to my corporate investment account. If I use margin to purchase corporate class ETFs can I write off the interest expense. I read that if it doesn’t produce a dividend that it would not be eligible. But I’ve almost read that investing in an income producing asset with the prospect of producing income is fine (the expectation it will produce income ie. grows).


r/cantax • • 6d ago

Buying a property under HoldCo?

6 Upvotes

I’ve asked Claude a few times but I don’t trust AI’s answer, so here I am, and here is the situation:

  1. ⁠Works full-time(T4)
  2. ⁠Owns a profitable corp, but my salary is enough to cover my living expense, so I’m not taking anything out of the corp

I’m currently exploring the possibility of buying a house under OpCo/HoldCo with mortgage, and rent some space to myself, some to corp as office, and potentially some to another person.

The whole reason I’m exploring is that you are not taxed by 55% by leaving the money inside the corp. That can go a long way especially with a large purchase like a house. And the rent I paid goes directly into my corp, which later on I can take out when the tax bracket is lower.

The question is, is it really advantageous from tax perspective? I’ve also heard it’s more beneficial to buy it under HoldCo for multiple reasons to manage risks.

Am I missing something?


r/cantax • • 6d ago

Foreign Land Inheritance and Deemed Disposition

1 Upvotes

I'm trying to help a family member navigate a foreign property inheritance and I'm stumped. Both the deceased and the beneficiary are Canadian residents. Where I'm stumped is around the deemed disposition and how CRA would calculate the taxes owing. Would they have to work with an appraiser to provide an approximate value at the time of inheritance? The property inherited is bare agricultural land in an obscure part of the world and I don't know what CRA would consider valid

Thoughts, insights, and experiences welcomed!


r/cantax • • 6d ago

Confused by whether or not 45(2) election applicable for non-resident , NR4/6 & Canadian agent to pay the withholding tax

2 Upvotes

Hi, I own and live in a condo in the GTA with no mortgage; this is my one and only primary residence in Canada. I will be leaving Canada soon and plan to rent it out. I purchased it back at the 2023 high, and I understand changing the usage of the condo requires a reassessment of the property. And obviously I want to avoid the value reassessment of my condo given the falloff of the housing market in the past few years. I know 45(2) can avoid the reassessment for 4 years, but I am extremely confused by: 1) Is 45(2) applicable to non-residents? 2) What will happen after the 4-year grace period ends? Do I need to hire someone to do the valuation assessment? 3) What if I come back to Canada and moving back into my condo within the 4-year reassessment grace period?

I am also a bit confused by the withholding tax thing & whether I need, and how to look for a Canadian agent to pay my rental income withholding tax. The only person who is really close enough to me that I could let her handle the monthly payment thing works at the CRA, too (though not in the rental income department), and for the sake of avoiding a conflict of interest of her job, I don't really want to bother her about this thing. Without a Canadian agent, how can I pay my withholding tax and submit my expenses for my condo (management fee, property tax, etc.), or i must still hire a property managment company for that? Thanks!


r/cantax • • 7d ago

Forgot to report $30K invoiced income on 2024 taxes and HST (Ontario). What should I do?

11 Upvotes

In 2024 I drove for Uber and also did $30K of invoiced contract work (no tax withheld, no T4A). I have a sole proprietor GST/HST account and a T4 job ($85K).
I filed my T1 and GST/HST return with only the Uber income and left out the $30K by mistake. CRA hasn't contacted me.
I estimate about $11-13K owing with interest. Should I file VDP (RC199) or just amend both returns? Anything to watch out for?
Thanks!


r/cantax • • 6d ago

T1135 late filing penalty relief

0 Upvotes

Hello,

I am a new immigrant to Canada. I moved here in 2024 from the US. I have a stock portfolio with Robinhood since before my move to Canada.

My employer had hired KpMG to file my taxes for year 2024. They filed the my taxes along with T1135 for 2024 before April 30, 2025.

I had to delY filing my 2025 taxes as I have some rrsp complications and documents on my US stock investments came early in april. So, I planned on getting it done by a CPA, so that they dont rush it during the busy season. Although I’ve made a lumpsum payment to CrA on April 28 on estimated tax I might be owing.

I was under the impression that T1135 needs to be filed along with the taxes. But today I learned that it is separate from filing taxes, and CRA would charge penalty upto $2500 for late filing T1135. Is there a way to get a relief from potentially getting penalized? I came across VDP or something but I am not sure if I will be eligible. Could you guys please suggest how can I get relief on this?


r/cantax • • 6d ago

Canada to US commuters any advice

0 Upvotes

Hello all, I live in YYZ and commute to ORD for work about 4 times a month so lets say Im in the US for half the month usually (I work in aviation). I’m a dual citizen getting paid in USD into my US accounts. I know the basics basically I pay IRS first, transfer that foreign tax credit over to CRA and pay the difference because CAD brackets are higher. Im not paying state tax too so am I subject to provincial taxes as well? Is it beneficial to change home of record to a US address entirely to save on taxes? If theres any that are out there in my similar situation please share! Thank you


r/cantax • • 7d ago

[ON] I keep missing my source deduction remittance deadline

7 Upvotes

I have a small incorporated business in Ontario with a few employees on payroll. I do the source deduction calculations and remittances to CRA myself, but this is now the second time I have been a few days late with the monthly PD7A and ended up with a penalty plus interest.

I understand why the deadline is what it is, based on the average monthly withholding. The problem is really just that I am doing it myself and it gets missed when things are busy.

For those with a handful of employees, do you use a payroll provider that handles the CRA remittance automatically, or do you just do it yourself with a reminder?

I’ve been looking at options like Folks HR, but I’m not sure it’s worth paying for payroll software just to avoid missing the remittance deadline. Curious what others with small teams are doing.


r/cantax • • 6d ago

For CRA staff, is there some reason why the T1135 form is not simply a part of the income tax filing? Why can't it be submitted online?

0 Upvotes

Some people overlook this report. Secondly, when one accesses their CRA account, there is no recap showing one even filed it.

I sent this form for my wife and I to a different address than our return. What if it got lost in the mail?

I see no reason why but could not simply be another schedule on the tax return.


r/cantax • • 7d ago

TD1/TD1-BC help???

2 Upvotes

(Crossposted from PersonalFinanceCanada)

Okay, Im desperate here. Ive tried to go the usual routes. Tried to call the CRA but it redirects me to automated line that doesn't answer my question. Tried to use the chat but its auto questions dont help and no agents are available. Refuse to use the AI not just for moral reasons but like. Im not fucking around with a hallucinating machine when it comes to my taxes???? No???? And I don't have time to dick around.

So I guess, heres the situation.

- I have one job, and I just got hired at a second job.

- my first job, I never had to fill out a td1 or a td1-bc

- therefore, I never claimed the basic personal amount, to my understanding???

- new job has me filling out td1 and td1-bc for taxes

- with my income for both jobs, Im making under the basic personal amount, so I know I check off "total income is less than the total claim amount"

Do i check off "more than 1 employer at the same time"? Because I DO have two employers, but it says "if you have more than one employer or layer at the same time and you have already claimed perspnal tax amounts on another form TD1 for 2026

...... if your total income from all sources will be more than the personal tax credits you claimed on another form td1, check this box" (emphasis mine)

And so, im confused. Because I DO have another employer, like I said. But I DIDN'T file a td1 before, so I haven't (??) Claimed my personal tax credits. And I dont make more than the amount??? So I don't know if im meant to check the box or not????? Do the personal tax credits get claimed even if im not the one claiming it if i work at a job???

Please help. Im supposed to have this in by thursday and I dont want to keep them waiting any longer than I already have. Ive never had 2 jobs before, and Im just really confused.