I read so much on this topic and I just can’t wrap my brain around it. Hoping someone here can help explain.

In 2025 I did a Roth conversion for $7,000. The regular IRA was funded with all post-tax money. I deposited $7k in the IRA account which had about $50 in it and immediately did the Roth conversion.
My understanding is that in this case the $7k should not be taxable. But the IRA account 1099-R shows $7k distribution and $7k taxable amount. This increased my total federal taxes owed by $2,491.
What am I missing?? Someone please help me make sense of all this.

So I filed for an extension originally due to this. I reached out to the business and my former manager a few times in March this year but didn’t receive anything back. I called the New York Department of taxation in March as well but they said they couldn’t make the company send a w2. I’m in college and don’t know much about taxes, how should I proceed with this?

Can anyone tell me what to do? I am filing tonight and just got rejected for not having my IP PIN. didn't know I had one, but no big - I'll just go to IRS.gov and request one. Except -

The Identity Protection PIN service is unavailable at this time

Identity Protection PIN (IP PIN) information cannot be updated. Please try again later.

Someone please tell me what to do so I can file tonight and not miss the deadline.

I want to double-check my maximum 2026 contribution limit for my Solo 401(k).

I have a W-2 day job (unrelated employer) where I fully max out my employee elective deferrals ($24,500). They also give me a small percentage match as an employer match contribution.

For my separate S-Corp contracting business, I take an $85,000 W-2 salary and want to contribute the maximum $72,000 via a 100% Mega Backdoor Roth strategy (voluntary after-tax contributions).

Can you confirm that under IRC Section 415(c), the $72,000 overall plan limit applies per unrelated employer? I want to ensure my day job's employee and employer contributions do not aggregate with or reduce my S-Corp's independent $72,000 limit.

I was 21 at the end of 2025, a full-time California college student, preparing my first federal and California returns. I have about $15,000 of taxable scholarships and $9,500 of earned income. FreeTaxUSA says I need Form 8615 and asks for parent tax information. My mother died; my father and stepmother live in Italy and file Italian, not U.S., returns. My father had a U.S. green card and SSN issued in the 1990s; I don’t know whether his green-card status formally ended. I also stayed rent-free with my uncle for eight months. How do I determine whether Form 8615 applies, and how is it completed if neither parent filed a U.S. return? Is there a way to file accurately if I cannot get that information by tonight’s extended deadline?

Both on the taxpros side and individual side. Payment history not available, transcripts not available.

Assuming it's a wide spread issue but want to double check

What a hassle. It is too late for me to get a second opinion today. I submitted all my info to my accountant on April 8. They said they need an extension...be done in a couple of weeks; I said no problem. I started bugging him at the end of August and here we are and he finally has my filing complete today.

The problem: I have issues with his interpretation on capital gains tax but all tax experts are busy with their clients on this October 15.

My tax preparer says I owe $70 K in taxes; I thought the figure would be closer to $30 K. If this had happened a month ago I could've paid for a second opinion and if I found an accountant who said my interpretation is right, I could've paid my tax preparer for his time and chose that other accountant do my taxes.

Any opinions on whether my case represents a significant dereliction of duty?

= = = = Capital gains tax question

Would be great if some expert would comment. My dad bought a condo in 1992 for $100,000 in Hawaii. He wanted me to inherit it and put it in trust.

Dad got married to wife 2. My stepmother started making issues with him changing his trust so my dad agreed to hold property with me as joint tenant. He signed this deed in 2016 -- property valuation $231,000. I knew this would cause me a tax liability, as opposed to transfer by trust.

Dad dies April 2025. I sell property in June 2025 for $445,000. I believed I would inherit his half of the condo and not pay inheritance tax. I believed that from the $445,000 we would subtract the $231,000, leaving an increase in value of $214,000. I believed this would be split 50-50, i.e., that I will pay property gains capital gains tax on $107,000.

My tax preparer says my capital gain is $345,000 --- $445,000 - the $100,000 that my dad paid for the property in 1992.

Thanks for anyone rendering an opinion.

I live in Florida, I loaned money with the agreement of being paid back in full after they sold their land. Needless to say they haven’t paid back anything if the money loaned. I doubt they will. I heard I could write this off as a bad loan deal what would I have to do to do this? I think I need to exhaust all options of getting the money back but this person is allusive to say the least and has moved a round the past year trying to get stable with her baby.

The amount loaned is significant and wouldn’t be considered a small claims in court. I don’t see them paying me back and they are not talking to me anymore. I’d have to hire a PI to tract them and serve them but even then idk if I could get anything from them. If anyone has any experience with the tax write off for something like this I’d appreciate any help.

I have what seems to be a somewhat unique situation (maybe not, but I can't find an easy answer). My Fiancee and I have some property we are considering selling and I want to make sure I'm reading IRC 121 correctly before we take any steps.

We purchased a property in October 2017. This property was used as our primary residence from 2017 through April 2024. In April 2024, we transferred ownership of the home to our LLC and have used it as a rental since then. We have had the same tenants in the property this whole time, and they have expressed interest in purchasing the property.

My question is, if the property is transferred back into our individual names before it is sold, are we still able to claim the §121 exclusion? By my calculation, we would have owned the property for at least 24 months out of the past 5 years and would have used it as our primary residence for the same amount of time. I'm just not sure if transferring ownership to our LLC causes any problems there. Thanks!

Will try to keep this concise. Appreciate the help!

Client is a Texas S-Corporation with 1 shareholder. Client received a form 592-B from a CA customer withholding 7% of the income they paid my client.

CA Franchise tax return has been prepared, and I applied some of the tax withheld on the 592-B received to the tax balance due.

For the remaining CA tax withheld to flow through to the shareholder, do I prepare a 592-PTE or a 592-B from the TX S-Corp to the shareholder? And the tax software is reporting the distributions on the federal form 1120-S as the Total income subject to withholding. Is that correct?

Hi everyone, im a recent undergraduate grad who officially started work in nyc in june. my annual income would be around 40k and ive submitted my w4 with no withholdings as a single filer. i understand that when it january comes around my payroll department will send over the w2s but i feel a bit lost on what i should expect regarding the upcoming tax season and how exactly to proceed on my part. i dont really have anyone around me to guide me through the process as a first timer and im doing my research but id figure id still ask. any tips and guides would be helpful and thank u in advance!!!

For example, I spent about $28k last year for marketing and advertising. $10k of that was lead purchases.

Does one large combined amount for these expenses work, or would it be better to list these out individually? Idk if this would make any difference at all in audit chances or anything else.

I purchased a house in Florida in 2025 intending to use it as an investment property. Unfortunately, the rental market was weak, tenant eviction issues and some failed to pay, and I had to deal with a lot of repairs and caretaking of some guests from Airbnb. I'm now living on part of the property and renting other, considering moving in fully by 2027 for 10 years and selling for the right price

let's assume the house is 400K and I earn $100K in W-2 income and incurred approximately $50K in property expenses in 2025, including mortgage, lawyer, inspection, furniture, interest, taxes, insurance, maintenance, and other costs. My original goal was to maximize deductions on the property purchase through cost study and accelerated depreciation, if i recall, called cost segregation However, I don't know what's the most tax-advantageous way to deduct or depreciate the property purchase and expenses for 2025?

Would cost segregation and bonus depreciation make sense, or would the passive-loss limitations prevent any immediate benefit against my W-2 income?

Lastly, does making it my primary residence later affect sales tax?

Hello everyone! I am a W2 hourly wage worker doing administrative work. I frequently worked OT during the 2025 year. My time sheet that I report every week shows the true hours I worked (for example 45 hours). My HR takes this and will put into the system for payment 47.5, just giving me my 1.5x pay for over 40 hours. They do not enter it as overtime. Can I go back week by week in my time sheets to get the “no tax on OT” amended on my tax return? Thank you!

I've had the same accountant for more than 10 years (they're in a small family office) and we have a good relationship, but I'm kinda frustrated right now.

As soon as I got my W2 this year in Jan I sent it to them and they ack receipt. Like 99% of my income comes from my W2 and it has been like that for a few years.

On April 15 they tell me they're extending the return. I ask about making a payment but they said they need to calculate and didn't know it then. I ask again after the 15th, a few times between april and july, but they never tell me an amount I owe. I was distracted with work and forgot about it.

They sent me the return to file this week and I obviously owe penalties and interest. I reminded them that I had been asking since April about making a payment and they didn't tell me. I think these payments could have been avoided.

Am I wrong for pressing them about it? It feels like they forgot, but they sure haven't forgotten about sending me the bill for these services

Hey all, I came to the US in the late 2022 yr and had no earnings given I was new to the country. I just looked at the year 2022 compliance report and it says it was filed late. I was wondering if this can be resolved by talking with the IRS as it’s not justified given I didn’t had the time to file the taxes with extention. What can be done here before I file for citizenship. I arrived in late September.

I’m honestly embarrassed to even write this, but I need some advice.

I went way overboard on sweepstakes casinos this year, mostly HelloMillions and Spree. Obviously I have a gambling problem. I’m done playing, but now I’m looking at the taxes and wondering how much worse I’ve made this for myself.

Going through my statements, I’ve put around $673k through these sites and gotten roughly $493k–$534k back. I’m still matching some payouts. That’s money being recycled over and over, not $673k I had sitting around. Either way, I’ve lost a substantial amount of my savings.

I’m in Illinois, single, and make about $50k from work, plus some investment income. I have bank statements, purchase emails and redemption confirmations. What I don’t have is a detailed history of my gameplay or a diary of my sessions.

I keep reading “just use session accounting,” but how do I actually do that without those records? A purchase on Monday and a payout hitting my bank Friday doesn’t tell me what happened in between. I’m trying to get records from the companies, but I don’t know what they’ll give me.

I’ve tried working through estimates with ChatGPT, and depending on the assumptions it’s thrown out everything from around $35k to $200k in total taxes before withholding. I know that isn’t professional advice or an actual bill. I need someone qualified to tell me whether those numbers even make sense, because right now I’m spiraling over them.

Has anyone here actually dealt with this? Especially in Illinois, or with these sites and missing gameplay records? What did your CPA need, and were they able to work with what you had?

I know I need to hire someone. I just don’t know whether I need a gambling CPA, a tax attorney, or both. If anyone has a referral or can tell me what to ask before paying someone, I’d appreciate it.

And if the bill really is huge, is there a realistic way to pay it over time without wiping out everything I have left?

I know I fucked up. I’m not asking how to keep gambling or hide anything. I’m trying to figure out what to do next.

Hi freaking out a bit. Will my taxes be timely if they are dropped off at 8:30 at a fed ex in Walgreens and paid for today? Person I was using is not doing them. I cannot get to the post office in time. I have foreign forms so it cannot be late. Thank you

As you can see from the title, it's a bit of a doozy.

My husband and I are moving to Japan. The company he's working for gave him a contract beginning in August. They requested that he get them the 6166 tax form so that his wages (in Japanese Yen) are not taxed in Japan... which would leave him double taxed in the U.S.

We felt this was the easier route than clawing back the taxes.

We've been checking in with the Philly office for turn around times and it seems they are about 1-2 weeks out from finishing the process.

However, the big question was about the Tick-box on form 8802 that says you must attest to being a resident of the United States until Dec 31. We asked the Philly office about going to Japan for the holidays before he "officially" started his job (which would be Jan-Feb)... They said this wouldn't pose an issue... but I don't think they are international tax attorneys and we want to be 100% sure this will not be an issue.

We're prepared to fly out Jan 1st, but there's a chance the CoE/Visa process can be completed by Mid November with the way everything is progressing.

Should we just wait or can we go to Japan before Christmas and be okay legal/tax-wise? Because we would be going to Japan under the working visa and not a tourist visa even though he technically wouldn't be working until January. (The contract explicitly states that he is NOT an employee of the company. He WILL become an employee of the company when he formally starts the job in Jan/Feb.)

Not that anyone would know, but we have the Japan side of things when it comes to taxes there and registering addresses on the immigration card. But I won't get into that ball of wax if it's not relevant to this.

Thanks!

My partner and I are California registered domestic partners. We’re still together but don’t live together.

She’s an independent student at a California community college, has no job or employment income, receives a Pell Grant, and has her enrollment fees waived.

We’ve been filing jointly for California, while I file Single federally and report all my wages and withholding. She hasn’t filed a federal return and reports no income on FAFSA.

I recently learned that registered domestic partners in California generally must split community income and related withholding between separate federal returns using Form 8958.

I’m trying to clarify:

• Does that requirement apply when we maintain separate homes?
• How is the community income handled for FAFSA and Pell eligibility?
• If prior tax returns and FAFSA information need correction, could past Pell payments become repayable?
• Could she keep her community-college fee waiver even if her Pell decreases?
• If repayment is required, could a payment arrangement allow her to continue attending and registering for classes?
• If we terminate the partnership going forward, when would that affect aid, given FAFSA’s use of earlier tax years?

I'm planning on reaching out to a tax adviser for next steps but was worried how this was going to play out and if she would be forced to stop going to school until it was repaid.

Hi, I need to file 5471, 8938, and 8949. Dormant corp, bank accounts and the sale of a property that I am not filing gains or loses. Looking for advice on which software to use. The corp was closed so I know I need to do a schedule O.

I had someone lined up to do all of this so please 🙏 no lecturing. I have an extension to today.

I live in Delaware and I need to modify my withholding to basically stop having Delaware take taxes out.

My employer uses adp and there doesn’t seem to be a way to actually do this.

I’m not exempt I’ve just already overpaid and don’t want a refund.

There are five more bi weekly paychecks in the year.

The form they give me only gives me a chance to update my allowances but no number there will stop the withholding.

Anybody have any experience with this?

Thanks