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Don't forget to check if you have any earnings that accumulated between your original contributions and the recharacterization/conversion. Those earnings ARE taxable in the year of conversion (2023 for you). The 1099-R total might be slightly higher than your contribution amounts because of those earnings. For example, if you contributed $6,000 but the 1099-R shows $6,150, that extra $150 would be taxable earnings. Since both recharacterizations happened in 2023, all taxable earnings would be reported on your 2023 return.
That's a good point! I did notice the 1099-R amounts were slightly higher than my contribution amounts. So if I understand correctly, I need to: 1. File Form 8606 for 2022 to establish non-deductible basis 2. On my 2023 return, report both 1099-Rs 3. Make sure Form 8606 for 2023 shows my total non-deductible basis 4. Pay tax only on the earnings portion (the difference between contributions and distribution amounts) Does that sound right?
That's exactly right! You've got the process down perfectly. Just to emphasize: make sure your non-deductible basis on Form 8606 for 2023 includes BOTH years' contribution amounts, not just 2023's contribution. The only taxable portion should be those earnings (the difference between your total contributions and the total distribution amounts on the 1099-Rs). TurboTax should calculate this correctly once you have all the non-deductible basis entered properly.
Just wanted to add one more point of confusion to watch for - the recharacterization process itself doesn't generate a 1099-R. The 1099-Rs you received are for the conversion from Traditional to Roth that happened after the recharacterization. Some tax software gets confused when you enter code '2' because it thinks you're taking a qualified distribution rather than doing a conversion. Double-check that TurboTax is treating these as conversions, not distributions.
Levi Parker
ā¢This is such an important detail! I got caught by this exact issue with H&R Block software. It kept trying to treat my recharacterization/conversion as a distribution I was cashing out. I had to go through some special screens to mark it properly as a conversion.
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Amina Toure
OP I'm in the exact same boat! I owed $2,700 this year after always getting refunds, and it was because of my side gig photography business. What tax software are you using? I found TurboTax Self-Employed was pretty good at walking me through all the possible deductions for my business, even stuff I hadn't thought of.
TurboTax is way overpriced. Try FreeTaxUSA - it's like $15 for state filing and federal is free. Has all the same self-employment stuff without the crazy price tag.
For the stock sale, hope you held them for more than a year! Long-term capital gains are taxed at a lower rate (0%, 15%, or 20% depending on your income) than short-term gains, which are taxed as ordinary income. That could be part of why your tax bill is high if they were short-term.
Is there any way to offset capital gains? I'm going to sell some stocks this year that will give me a big gain and I'm dreading the tax hit.
Yes, you can offset capital gains with capital losses. If you have investments that have gone down in value, selling them in the same tax year will create capital losses that directly offset your gains. You can also contribute to tax-advantaged accounts like 401(k)s or traditional IRAs to lower your overall taxable income, which can help reduce the impact of the capital gains. For example, if contributing more to your 401(k) drops you into a lower tax bracket, your capital gains rate might also decrease.
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Lola Perez
One thing to consider: make sure you check if your current doctors are in-network for any plan you're considering on Healthcare.gov. I made that mistake when I lost my job in 2023 and ended up having to find all new providers. Also, look closely at the prescription coverage if you take any regular medications. Some plans have really high deductibles before prescription coverage kicks in.
I didn't even think about checking if my doctor is in-network! Thanks for pointing that out. I take a maintenance med for high blood pressure so I'll definitely check the prescription coverage too. Is there an easy way to see which plans include specific doctors? The Healthcare.gov site seems a bit overwhelming with all the plan options.
Lola Perez
ā¢Most plans on Healthcare.gov will have a link to the insurer's website where you can search for specific doctors. But honestly, the most reliable method is to call your doctor's office directly and ask which marketplace plans they accept. The online directories are sometimes outdated. For prescriptions, look for the plan's "formulary" - that's their list of covered medications. Different tiers have different costs, so check which tier your medication falls into. Some plans also offer prescription discounts before you meet your deductible, which can make a big difference.
What state are you in? That makes a huge difference for coverage options. Some states run their own exchanges instead of Healthcare.gov.
I'm in Illinois. From what I've seen, we use the federal Healthcare.gov site, right?
Riya Sharma
ā¢Yep, Illinois uses Healthcare.gov. But worth noting that some states have additional programs beyond what's on Healthcare.gov. For example, if your income is low enough during your unemployment period, you might temporarily qualify for Medicaid in Illinois, which could be free or very low cost until you find a new job.
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Has anyone had luck with those online CPA services that specialize in digital businesses? My wife's doing something similar with affiliate stuff and regular accountants just don't seem to get all the nuances of online business expenses.
I've been using Xendoo for my ecommerce business for about 2 years and they've been really good. They specifically get digital business models and understand things like affiliate commission structures, digital asset depreciation, and home office setups for online work. Not the cheapest option but definitely worth it for the specialized knowledge.
Demi Lagos
Don't overlook the importance of finding someone who's comfortable with technology. I had a "well-established" CPA who insisted on paper documentation for everything, which was a nightmare for my digital business where most receipts and records are electronic. Finding someone who understands digital record-keeping made tax time 10x easier.
Lucas Adams
We're actually using a combination of solutions that works well for us. For document storage and management, we use ShareFile with a standardized folder structure for each client. For workpaper preparation and review, we use CCH Engagement. The key for us wasn't really the software itself, but creating standardized processes and enforcing them. We have templates for every type of return with standard workpapers already set up. Each workpaper is numbered according to the tax form line item it supports (for example, Schedule C workpapers all start with C-). Our review process requires reviewers to sign off on each workpaper electronically, which has dramatically improved our quality control.
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Harper Hill
ā¢How did you handle the transition to CCH Engagement? Did you have to convert a lot of existing documents? We're currently using a hodgepodge of Excel workpapers and I'm worried about the time investment to switch.
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Lucas Adams
ā¢The transition did take significant effort, but we did it gradually over about a year. We didn't try to convert historical workpapers - instead, we started using the new system with new clients first, then gradually transitioned existing clients as they came in for the next tax season. We created a core set of templates and standard workpapers before we rolled it out to the team. This upfront investment paid off tremendously as it ensured consistency from the beginning. We did need training from CCH to get everyone up to speed, but that was worth the investment.
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Caden Nguyen
Has anyone tried Canopy for workpaper management? We're considering it but not sure if it's worth the investment.
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Avery Flores
ā¢We used Canopy for about a year but ultimately switched to SmartVault. Canopy has some nice features for client communication and task management, but we found the document management aspects to be less robust than we needed for complex business returns. The interface is clean and user-friendly, but it was missing some advanced referencing features that we wanted. If your practice is primarily individual returns with some simple business returns, it might be sufficient. For a practice with complex business clients, you might find it limiting.
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