


Ask the community...
One thing nobody has mentioned yet - if you have ANY other Traditional IRA assets with pre-tax money in them (like from old 401k rollovers), the conversion option gets more complicated because of the pro-rata rule. The IRS won't let you just convert the non-deductible portion - you have to convert proportionally across all your Traditional IRA assets. Recharacterization avoids this issue completely since it's like the Traditional contribution never happened. So if you have other Traditional IRA assets, definitely go the recharacterization route while you still can!
Oh that's really good to know! I actually do have an old 401k that I rolled into a Traditional IRA last year. So if I did conversion instead of recharacterization, I'd have to convert some of that old 401k money too and pay taxes on it?
Yes, that's exactly the issue. With the pro-rata rule, you can't cherry-pick which dollars to convert. If you have $9,500 in non-deductible contributions and, say, $40,000 in pre-tax money from your old 401k rollover (all in Traditional IRAs), then any conversion would be proportionally taxable. If you converted $9,500, about 19% would be considered non-taxable (your non-deductible portion) and 81% would be taxable. The IRS looks at all your Traditional IRAs as one big bucket for this calculation. Recharacterization bypasses this completely since it's treated as if you never contributed to the Traditional IRA in the first place.
Anybody have experience with Fidelity handling these recharacterizations? Their website is confusing me. Do I need to call or can I do it online?
I did a recharacterization with Fidelity last year. Had to call - couldn't find any way to do it online. The phone rep was actually really helpful and processed it while I was on the call. Had to confirm I understood the tax implications but it was pretty straightforward once I got through to someone.
Hey just wanted to add - I was in a somewhat similar situation with the First Time Homebuyer Credit a few years back. The one thing I learned is that you should stop making those $500 payments ASAP if you have documentation proving your closing date was in 2009. The reason is that continuing to pay acknowledges the debt. Talk to a tax pro, but in my case, I was able to get the IRS to recognize that I had incorrectly categorized my purchase date and should have received the non-repayable credit. I didn't get back what I'd already paid, but I was relieved of future payment obligations. Make sure you keep ALL your closing documents safe - you'll need them if the IRS questions why you stopped making payments.
Did you have to file any special forms when you got them to stop requiring repayment? I'm worried if I just stop paying the $500 installments it'll trigger some kind of automatic collection process. Did they give you any pushback or was it fairly straightforward once you showed them the correct closing date?
I had to file a Form 843 (Claim for Refund and Request for Abatement) along with a detailed letter explaining the situation. I attached copies of my closing documents clearly showing the 2009 date, plus copies of my original tax returns where I made the mistake. The IRS did initially send some automated notices when I stopped making the payments. That's why it's important to be proactive rather than just stopping. They eventually processed my claim and sent a letter confirming I was no longer responsible for the remaining payments. It took about 5 months total from submission to resolution.
Just a quick tax tip that might help others - the First Time Homebuyer Credit had different versions depending on when you purchased: - April 9, 2008 - Dec 31, 2008: $7,500 credit that must be repaid over 15 years - Jan 1, 2009 - Nov 6, 2009: $8,000 credit with NO repayment required - Nov 7, 2009 - April 30, 2010: $8,000 credit for first-time buyers OR $6,500 for long-time residents So the OP definitely got caught in an unfortunate timing situation by accidentally claiming the 2008 credit when their purchase was actually in 2009. Just 3 days difference between a loan and a true credit!
That's why I always tell people to triple-check dates on major tax credits! The government loves to create these weird cutoff periods that can cost you thousands. I had a client who missed the solar tax credit by ONE DAY because of installation timing. Brutal.
One thing nobody has mentioned yet - make sure you establish a health insurance plan reimbursement arrangement through your S corp in WRITING. My accountant said this was critical. We created a simple document that outlines how the S corp will reimburse health insurance premiums for employees (just my wife and me). Without this written plan, the IRS could potentially disallow your deductions during an audit. Also don't forget that the deduction for S corp health insurance is limited to your business income. If your S corp has a loss for the year, you can't deduct the premiums.
Do you have a template for that written plan? Or did you have your accountant create it? I'm trying to figure out if this is something we can do ourselves or if we need professional help with it.
I created it myself based on some research, then had my accountant review it. It doesn't need to be super complex - mine is about 2 pages. It basically states that the corporation will reimburse employees (including shareholder-employees) for health insurance premiums up to a certain amount annually. Key elements to include: effective date, eligible employees, what expenses are covered, maximum reimbursement amounts, how/when reimbursements will be processed, and documentation requirements (employees need to submit proof of premium payments). You should also state that it's intended to comply with relevant tax regulations.
Marketplace insurance might actually be a good option since you mentioned you left your job recently. You'd qualify for a Special Enrollment Period due to loss of coverage, so you don't have to wait for open enrollment. For our S corp, we found that getting individual marketplace plans and having the company reimburse us worked better than a group plan because we qualified for premium tax credits based on our salary (not including distributions). You do need to be careful about how you structure your salary vs distributions to maximize the benefits.
I did this with my S-corp and it works well, but make sure you understand the income reporting. The marketplace uses MAGI (modified adjusted gross income) to determine subsidies, which includes your W-2 wages plus business profits passed through to your personal return.
Just to add some perspective from someone who's been through this: I didn't file for 6 years (2009-2014) and finally got everything squared away in 2015. Here's what happened: 1) For the years I was owed refunds, I got them (except for the ones past the 3-year limit) 2) For the years I owed taxes, I had to pay penalties and interest 3) I set up a payment plan for what I owed 4) Life went on and everything was fine NO JAIL TIME. No scary agents showing up at my door. Just some paperwork and eventually a monthly payment that was totally manageable. The anxiety of not filing was WAY worse than actually fixing the problem.
Thank you so much for sharing your experience. That makes me feel a lot better. Did you use a tax preparer or did you do it yourself? And about how much were the penalties as a percentage of what you owed?
I used a local tax preparer who advertised help with unfiled returns. Cost me about $175 per year to prepare, but it was worth every penny for the peace of mind. The penalties ended up being roughly 25% of what I owed, plus interest that had accumulated. So for example, one year I owed about $2,200 in actual taxes, and the penalties/interest added about $800. Not fun to pay, but definitely not the financial apocalypse I had built up in my head. The payment plan let me spread it out over 36 months too.
Has anyone else noticed that tax filings for previous years require using old tax forms? I just went through catching up 3 years of taxes and got confused because the forms change slightly year to year. Make sure you're using the correct year's forms and tax software when you file! The IRS website has previous years' forms but it can be confusing to navigate.
Yes! This tripped me up too. If you're using software like TurboTax or H&R Block, make sure you buy the specific year versions for each past year. Current year software won't work for prior years.
Malik Johnson
Something nobody's mentioned yet - gas stations are regulated differently than most businesses. In many states, there are specific laws about how gas prices are displayed and advertised. Some states actually require gas stations to show the lowest price (cash price) on their big signs. Also, gas stations often pay higher processing fees than other retailers because of the high dollar amounts and fraud potential. The card networks classify them as "high-risk merchants" which means higher rates.
0 coins
Isabella Santos
ā¢Do you know if there's any regulation about how much extra they can charge for credit? My local station is charging almost a dollar more per gallon for credit vs cash which seems WAY more than the actual processing fee would be.
0 coins
Malik Johnson
ā¢The regulations vary by state, but generally there's no strict limit on the price difference. However, in most states, they do need to clearly post both prices. Some states like California have regulations requiring that credit card surcharges can't exceed the actual cost to the merchant, but enforcement is spotty. The large difference you're seeing (nearly a dollar) is definitely more than just covering the processing fee. It's likely they're using the cash discount to encourage a payment method that has other benefits for them - faster settlement, no chargebacks, and possibly some unreported cash transactions. It's a way to improve their overall margins in a business with typically very thin profit margins.
0 coins
Ravi Sharma
Former gas station manager here. The credit/cash price difference isn't just about processing fees and tax deductions. There's more to it. 1) Cash payments are immediate. Credit card payments can take 2-3 days to process, which affects cash flow. 2) Cash transactions have no risk of chargebacks, which are a huge headache. 3) Cash transactions are faster at the pump, meaning more customers served. 4) Credit card companies charge higher rates for premium cards (those 2% cashback cards cost merchants more). Yes, the processing fees are tax deductible, but like someone else said, that only saves us about 21% of the actual fee. We're still paying the other 79%.
0 coins
Freya Larsen
ā¢Is it true that gas stations make almost no money on the actual gas and make all their profit on the convenience store stuff? I've heard that's why they try so hard to get people inside the store.
0 coins