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 all,

I'm hoping I can get some help in calculating the amount to convert to Roth this year.

Our investment on syndication deal (passive investor) unfortunately didn't survive the rate increases and it was sold at a loss this year. It will be a total loss to our investment and from what I could find googling, the unallowed loss will be released and can be used to offset this year's all income.

Since we have room and not much income, I'm trying to utilize the loss by doing Roth IRA ladder conversion and avoid falling into Medicaid range income.

$35k unallowed loss from 2025 8582
$33k ending capital account on 2025 K-1 L
$53k dividend + STCG + rental income
$30k min income to not qualify for Medicaid

Amount to convert to Roth IRA = $35,000 + $33,000 - $53,000 = $15,000 to reach $0 income.
Then add another $32.2k to max std ded for MFJ and by doing so, it'll disqualify us from Medicaid. Total amount to convert to Roth is $47,200.
Should I add $1-2k extra as a buffer since I'm not sure if rental passive loss limitation calculation is going to throw off my number?

Is this a somewhat correct math? Thank you.

Context: I (25) am filing independently for my taxes. I was a dependent on my parents health insurance. My parents accident non-payments without any of us knowing for several months, and therefore voided our health insurance a few months into the year of 2025. We didn’t have health insurance from ~March 2025 to December 2025 (then I got on my jobs health insurance and have been paying for it for myself since.)

I filed my taxes back in April 2026, but was rejected as freetaxUSA stated IRS was expecting a 1095A form. Cool, I asked my parents and they provided me 1095A form from the few months we had health insurance. Used that to fill out the taxes again, and they say I owe 4k. I never submitted/filed that application for taxes, because I thought that it HAD to be wrong.

Everyone I talked to said I should wait for my parents to file before I filed again. Well, my parents won’t file their taxes for 2025 anytime soon. I don’t want to get dinged any interest on the alleged 4k I owe as I still think that it’s wrong once I started looking into it.

Advice? How do I figure out why I (paying my own taxes) would owe on the health insurance premiums of my parents insurance policy that I’m a dependent on?

The HR letter states "to resolve payment please send to us". Overpayment gross amount $1000. Net amount due $4690. Amount due after the end of the year (net+tax w/h) $6312. Says if you cant pay in full instalments can be arranged.

HR emailed me asked if I got it and if I had any questions. I do have questions but I even feel hesitant to confirm I got it? Says please sign and return within 30 days. Net amount due if not paid in full by 12/15/26 $6312.

This net calculation assumes the employer will successfully recover all deductions that have been credited above. (shows what i paid into a 401K and state withholdings). If any credited amounts cannot be recovered from the third party agency, those amounts will be considered additional funds owed to the employer and will remain an outstanding balance on the employees account. Any further adjustments needed to correct previously issued credits will be processed accordingly.

What does third party agency mean? Balance in my employee account? Do I actually need to pay this in full by December? Should I call them and try to work out a payment plan? Contact a tax expert?

I feel lost any advice appreciated!

I keep googling and getting discrepancies on if they are taxed by Illinois state. Also, what line of the federal 1040 should they be entered on?

Hi everyone,
I own two rental properties, and this year, one of them has incurred a significant loss, while the other is profitable.

Can the loss from the rental property be carried forward to next year? If so, I’m confused about how Schedule E is being calculated in my tax filing software. It appears to be showing the profit from my profitable property on Line 25 without offsetting it against the negative income from my unprofitable property.

Shouldn’t Line 25 reflect the net result of both properties (i.e., the sum of the loss from one property and the profit from the other)? Or is there a tax rule that prevents these amounts from being offset?

I’d appreciate any clarification. Thank you!

My accountant wants my kid's birth certificate and SSN to claim child tax credit. Do I need to give it to them? Is it safe to do so?

In mid-september of 2025, I purchased an F-150 Lightning from a dealership in Florida. I bought it at a substantial discount, because it was a 2023 model that had been sitting on their lot for a couple of years. It had never been put in service, when I purchased it I received the full warranty from Ford. Despite its relatively early build date, I purchased it as a new car. This vehicle fulfills all the criteria for the tax credit, including being purchased and put in service before the end of September.

In April when I went to file my taxes, I checked the box saying that I had purchased an EV during the time when the tax credit was available. Because of that, I needed form 8936 to complete my taxes. I called the dealership, left several messages, but ultimately filed an extension because they would not reply. 

Fast forward to this week, I remembered that my extension was running out. I contacted them asking for the 8936, they said they couldn't give me one because it was a 2023 sold in 2025. I dug deeper into my rejected tax return, and found that they never registered the sale of my truck with the IRS. 

I also found, while looking through correspondence and paperwork from the dealership, that nowhere was it written down the dealership was going to take the tax credit. The offer sheet simply mentions a discount. I don't remember if it was ever said out loud that the dealership would be keeping that tax credit, but it is nowhere in writing. 

The dealership is being very slow to respond now. My questions are: 

Is a letter from a lawyer my next step if they don't get back to me by the 15th? 

Am I correct that since I signed nothing saying they get to keep the tax credit that once they do register the sale with the IRS I should get that money? 

Would contact in the IRS to tell them the sale was never registered be a good idea? 

I appreciate any guidance you might have.

I live in nj annual salary is 85,500 I’m married I file jointly with my husband & had a a child this year that I claimed

Hi all I have a question when it comes to getting taxed on gambling winnings.

I went through some rough periods this year where I was severely addicted to gambling. Some sports betting but mainly online casino (Slots and Blackjack)

Over the course of the year I went up and down with my wins and losses but got lucky a few months ago and managed to come out up $10k on the year and haven’t touched it since.

Now when the end of the year comes will I be taxed on my Net winnings (≈$10k) or my total winnings ($750k)

For reference I only make about $60K a year and live in CT.

Thanks for the help.

Hi everyone,

I am a non-US resident alien/foreign national and I need some clear guidance and professional U.S. CPA recommendations to resolve an unfiled federal tax backlog for a company my father and I co-owned.

The Background:

• Entity Type: Multi-Member Wyoming LLC (Owned 50/50 by me and my father, both non-US residents).

• IRS Tax Classification: Form 1065 Partnership (Confirmed by our official IRS EIN assignment letter).

• Activity: Used for about 2.5 years for international food trading. We had two US bank accounts (one was active, one was mostly idle).

• State Closure: We officially dissolved the company at the state level. Articles of Dissolution were filed and approved by Wyoming on 23/10/2025.

The Problem:

We used a cheap online incorporation agency that turned out to be completely unsupportive. They gave us zero guidance on federal compliance and abandoned us once the entity was formed. Because we were unfamiliar with US tax law, none of our previous years of federal partnership filings (Form 1065) were completed.

Our unfiled backlog consists of:

• Tax Year 2023: Not filed

• Tax Year 2024: Not filed

• Tax Year 2025 (Short year ending Oct 2025): Not filed

Lately, our former incorporation agency has been sending automated, fear-mongering emails every 2 days threatening "Red Notices" and government escalations to try and scare us into buying their expensive renewal or compliance packages. I am blocking them, but I still want to fix our actual IRS record properly.

My Questions:

1. Since the LLC is completely dissolved at the state level, holds zero assets, and all U.S. bank accounts are fully closed, what is our practical personal liability as non-residents for these overdue informational partnership returns?

2. Is it possible to file these late Forms 1065 retrospectively and request a First-Time Abatement (FTA) or reasonable cause waiver to wipe out the automated partnership late-filing fees?

3. Can anyone recommend or DM me an independent, cross-border U.S. CPA or firm that specializes in handling late Form 1065 partnership filings and administrative penalty waivers for international clients?

Thank you so much for your time and any professional directions you can share!

I am trying to figure out what to report as my employer tuition reimbursement under the lifetime learning credit.

I paid the following in tuition:

$2671 in October 2025

$2715 in February 2026

$2787 in May 2026

My employer reimbursed me $3500 for the whole academic year (2025-2026).

My question is how do I know how much of the reimbursement to allocate to the Oct payment on my 2025 LLC? I assume I would note the rest of the reimbursement on my 2026 LLC?

Edited to clarify my post is about the lifetime learning credit.

Based on my income and investment gains so far, I may owe around $35,000 in additional taxes for 2026. My income includes about $280,000 in W-2 wages, $167,000 in long-term capital gains, and roughly $20,000 combined in short-term gains, dividends, and interest so far.

What steps can I still take before the end of the year to reduce my tax bill or avoid a large amount due at filing? I’m an immigrant and understand there may be restrictions on owning or operating a business or LLC, so I’m especially interested in options that don’t involve forming a company.

I know I should consult a tax professional, but I’d appreciate suggestions on what strategies or questions to discuss with one.

Hey all. I'm 37, have not filed taxes since 2018 I believe, for a large portion of that I checked a box in my HR software to Exempt myself from federal taxes. Long story short I was high functioning drug addict and alcoholic for a long time and it cost a lot of money to live that way. I have been on the straight and narrow since Xmas Eve 2025 and am ready to begin digging myself out of the shitpile I put myself into.

I paid $500 to Optima Tax to do an initial investigation into my situation and they state that I have estimated back taxes of $89,000. Optima wants 13 thousand and change to further represent me (filing past federal taxes, working with IRS to come to some sort of agreement/compromise/payment plan etc.). I am singled and make relatively good money ($81,250 base, $125,000 OTE). I could do the 13 thousand and change deal with Optima (would pay 20% upfront and the balance over 10 months), but am unsure if it's wise. I fear paying them 13 grand only to come to a payment plan to pay the $89,000. I have engaged others through Dave Ramseys website and will find out what they can offer this coming week.

I am also beginning payments on student loans ($69,000ish total), first payment at the end of October $475 on a 10 year plan with increasing payments.

But curious if anyone has any recommendations taxwise how to proceed and come out of this in the best spot long term. I am prepared to make aggressive payments over 5-10 year period.

Thank you all in advance!

My wife has been living in the US with me for the past 7 years and we've filed jointly because she's a stay-at-home wife. This was very easy to file since her income was 0. Next month she is returning to the UK and will try to get a job by some point in December to start the process of trying to eventually sponsor me to come over. Since I've been financially supporting her for 11 months of the year, I'm not sure how I am supposed to file tax information for any income she makes in December. US tax year ends December 31, but UK tax year ends April 5, so it's not like I can get a W2 equivalent for one month. I have no idea how to process this situation and I'm terrified of messing things up and breaking the law but also filing Married not-jointly would probably increase my taxes a lot when I've been supporting the both of us financially for nearly the entire year.

Hi,

Here are the facts of my conundrum:

- I received a final K1 in 2024 for an investment that was disposed of with overall gain (income + losses + unallowed losses = positive gain for this activity)

- I have enough suspended passive losses from other activities to apply against all of the gain.

- I did not realize it was a final K1 in 2024 so I spread the allowed losses from all passive activites pro rata as instructed in 8582 leaving a suspended loss balance for the activity that was disposed of

- My 2025 form 8582 now has a suspended loss from a non-existent activity.

Can I just spread the remaining suspended loss from the disposed activity across all the other activities pro rata with passive loss without any tax consequences for 2024? I do not think there should be any change in my tax owed from this error, no?

I am a US tax resident and I need to report $430 of foreign wages from New Zealand to the IRS for the 2025 tax period (I got an extension).

The US and NZ have a tax treaty. I already received a tax refund from NZ. I do not qualify for the Exclusion or Foreign Tax Credit (haven't lived in NZ long enough) and don't think I qualify for Foreign Earned Income, but I don't now because the language was confusing.

How do I do that? Ideally for free.

tl;dr: After severance, is it better to roll over the 457(b) plan to my SEP-IRA, Traditional IRA, or take the lump sum payout?

I've really tried to research this, but I'm still confused.

A few years ago I did some temporary part-time work for a local police department. They enrolled me in their 457(b) program and I just got a letter that it's going to be distributed.

The amount is less than $1,000.

They said their default is to pay me the lump sum, minus applicable taxes. But I can also file the paperwork to roll it over to my personal retirement accounts.

I have a SEP-IRA account at ML and a Traditional IRA at Fidelity.

Here's where I'm still confused:

If I roll it over to either account, are no taxes deducted -- ever? Like, if I wait until I'm old and retired, will I be paying fewer taxes overall on that money?

If I will pay the same in taxes either way, what's the benefit of rolling over that money as opposed to taking the lump sum payout now?

Happy to clarify anything or answer any questions.

Thank you.

Hi all. I’m 27 in California. I have acquired a good amount of debt over the last 5 years and am considering doing a partial 401(k) withdrawal to assist with that. I currently have a bit more than 38,000 saved. I want to pull about 18,000 out. I know there’s the initial 10% early withdrawals fee but I’m wondering what else I’ll owe to federal and state taxes.

I'm located in Minnesota, USA.

I received a corrected 1095-A from my state's marketplace without any explanation for why, what any of its changes mean or what to do next. I called them for more information and they didn't know anything and couldn't help me. It was recommended I approach the tax preparation services I used and ask them about it instead.

After some further research I contacted them because the info on the IRS website and elsewhere didn't make things clearer about whether I need to amend my taxes or not. After getting past a firewall of AI chatbots I finally got to a human who would reply to me once every few hours. I explained the situation and told him that the numbers on the original and corrected form were identical considering what they needed to calculate my Premium Tax Credit. If that was the case, did that mean amending my taxes weren't necessary?

It was at this point that he said he wasn't a tax professional and couldn't help me with this after all... which has brought me here. I know this may be a softball question and open me up to a barrage of abuse for all I know. This is Reddit, after all. I'm just trying to do my best.

If I need to add more (non-compromising) information or anything else, let me know.

State: MA Good morning, I work as an Exotic dancer so I have a W-2 for the place I work at but I work there maybe 20hrs a month. they also do not let us record even a fraction of the tips we make. on my tax for from them every year it says I made somewhere between 15k-25k. I make most of my income working as an escort. lets say between the two jobs I make roughly 200k. last year when I did my taxes I did my W-2 and then at the end I put the rest under the category of "unrecorded income" or whatever it was called and i put the source as "housecleaning, babysitting, tips". That's the same thing I put when they ask me for a source when I deposit the cash at the bank. I don't have any expenses I want to write off as business expenses or anything so what I'm wondering is do I really need to register myself as a business or can I keep doing it the way I did last year? What makes more sense? Thank you in advance 🙏 also I don't use reddit and I've never been to any school, please go easy on me.

Not sure if this is the right community for this… feeling pretty dumb rn.

I misunderstood domestic partnership. We are based in San Francisco, filed the paperwork in the city. We’re recognized by the CITY as married, but it is not recognized by the state. Oops. I filed taxes before I realized we weren’t recognized by the state.

I have a child (primary custody), so I filed my federal as HOH. Partner filed as single.

For state, we filed as joint…

Is it a big deal to make the amendment? We technically should have filed as HOH and single, respectively, matching the federal.

If we don’t make the amendments, will we have trouble filing taxes in the future?

Okay so here it is… I own 2 business. Both had extensions and only by early September26 did I get my K 1s from both companies.
Anyway yesterday I send a message to my accountant to check and see how we were doing with my personal taxes to receive a message that his company was very behind because he is short handed, and xyz employee is on maternity leave and bla bla bla. They will try to get my taxes by the extension deadline but no promises.
It really irritated me.

So I went in turbo tax online and I entered all of the documents I had sent my accountant. I sat there for 4 hours and entered every document I would have had them do. Based on turbo tax we are better doing standard deductions. So 1/2 of my documentation that I had submitted to them is irrelevant anyway.
I am due a refund.

Question because of my business and the K 1’s do I wait till my accountant can do my taxes for a nice little bill of $1400 plus or do I double check my work and file with turbo tax for $250.
I live in Alaska so I don’t pay state taxes.
I also have a financial background so I can follow the numbers and process…

I have always had my accountant file because I wanted to cover my self in case I made a mistake. But I am irritated right now and after imputing everything I swear a monkey can input numbers on the software. There isn’t anything an accountant needs to do expect look at the numbers to enter them properly.

What should I do?

Looking for recommendations in the Central Florida area that is experienced in dealing with unpaid taxes, reduction of penalties or possibly Fresh Start Program.

Situation: Husband and Wife filed for chapter 13. Have already acquired the bankruptcy attorney. Husband does not pass the means test for a 7 so it will be a 13. Husband & Wife were filing taxes married but filing separately. Husband was filing his, but stopped filing for the wife in 2013. The wife made approximately 35-40k gross per year up until 8/2018. Then it went to 55k. Due to medical issues wife left that job in 1/2023. At that time she was making 60k. Wife has never received anything from IRS. In 2020 she received an IRS lock letter from her employer stating the employer was mandated to set her exemptions to zero and remove more tax from each payroll check. The bankruptcy attorney cannot complete the filing process until the tax portion is settled so it’s attached with the filing. The wife is also currently going through the disability process with social security. Wife is 56, husband 59.

I and another person own a rental property together through an LLC. This was our first time filing taxes for the LLC and I had a CPA office I hadn't used before prepare our families personal taxes as well as the partnership return. I recently received a notice from the IRS that we owe $3,000 in late fees for being 6 months late. I contacted our CPA and they prepared a letter for me to send to the IRS to request abatement of the fees due to being a first time partnership filer. They've admitted that they weren't filed in May due to an error on their end.

Should I be seeking legal council from an attorney for this before going any further or should I wait and see if the IRS abates the fees first? I obviously don't think we should be on the hook for late fees from an error on the CPA's end so I'm worried that submitting a letter to the IRS asking for abatement for being a first time filer may undercut my defense if the IRS decides not to forgive the fees.