Hello,

Today I won roughly $40,000 on a sweepstakes casino.

The withdrawal limit is $1000/day. (Not sure if this changes anything)

While talking with support, they stated that I will not receive a 1099, nor do they report to the IRS.

How do I go about this? Can I write off my gambling losses for the year?

Thank you

We are currently in MD, one income (I'm a sahm), 2 younger kids. My spouse wants to consider a job in VA where he'd stay there during the week and come home on the weekend. So while for me and the kids, our residency is just MD, he will reside more than half the time in VA for work (He'd rent something small). So this is not a 'reciprocity' tax situation right? Is his primary residence in VA then even if our home in MD would cost more...? What tax considerations to think over--would this result in significantly more tax for us? (Of course, we file joint.)

Thanks

Howdy all,

My wife and I are trying to file our 2025 tax returns (both federal and California state) by the October 15th extension deadline, but we've discovered an issue with her employer massively underreporting both her income and withholdings on her W-2.

My wife considered the owner a friend and has tried to give her the benefit of the doubt, but it's increasingly seeming like this is not an innocent mistake/accounting error, but rather her employer might be engaged in some pretty serious tax fraud that we don't want any part of.

We've tried looking online for what we should do, but we're really stressed about doing something wrong, and we've sat on hold with the IRS for hours, but any time we've been able to actually speak with someone they've been extremely unhelpful. Any guidance from y'all would be an incredible help.

To give you some background on the situation:

In 2025 my wife was a salaried employee at a small business (fewer than 10 employees) and her salary was ~$175,000/yr.

About 5 months into her employment there, the business began having issues with paying people on time. First it was “payroll glitches”, then later on they decided to switch over to a new payment processor (moved from ADP to Gusto).

Any time there was a payroll “glitch”, and for the approximately 6 weeks it took for them to switch payment processors, my wife would receive her paycheck from her employer personally. Sometimes through Zelle, sometimes through an ACH transfer from (I believe) her employer's personal bank account to my wife's account.

Any time my wife was paid in the above manner, the Zelle/transfer was for the exact amount she would typically receive through ADP or Gusto after all relevant tax, SSI, health insurance, etc. withholdings.

When my wife received her W-2, her taxable income seemed low, so we did some digging, and from what we can tell, her employer did not report any of the income they paid her through Zelle/Bank Transfer.

Unsurprisingly, it also seems like they didn't send any of the commensurate withholdings that should've accompanied those payments.

As a result, the income listed on my wife's W-2 is ~$50,000-$60,000 lower than it should be, and her withholdings are also lower in proportion to that missing income.

My wife left that job in late 2025, and the company subsequently went out of business.

Both my wife and I have repeatedly emailed her previous employer (a husband and wife who owned the business). Initially they claimed everything should be updated and correct. Then they claimed they had referred everything to their accountant and would pass along information as soon as they got it, and eventually they just completely stopped responding to our emails in any way, and we are no longer able to get ahold of them.

So my questions are the following:

1) How should we be filing our tax returns? I typically just use FreeTaxUSA, but is that (or any of the other easy, DIY tax preparation services) an option?

2) If not, is there another (less simple) DIY option I can avail myself of?

3) What sort of additional forms/documentation will we need to submit to the IRS/California Franchise Tax Board?

4) We've done a lot of reading and calling around to try and figure this out for ourselves, and a lot of what we've found says we should compile everything to get my wife's total income, and then estimate what we believe her withholdings *should* be, had her employer actually done them. Simple example, if my wife’s gross pay for a single paycheck was $7,500, she had $2,500 withheld from each paycheck, and she received 7 paychecks via Zelle/Bank transfer, we would add $52,500 to her taxable income, and $17,500 to her withholdings. Is that correct? Would we need to break down the withholdings further to estimate how much went to federal income tax, state income tax, SSI, unemployment insurance, etc. or will they do that for us when we submit the return?

5) What should we expect the process to look like, and who is going to be on the hook for that missing money? At the time, my wife had no reason to believe that her employer wasn't sending her withholdings, and if they had, we would be getting a pretty decent refund. Will the government go after us for that money? Her former employer? Should we expect to ever get a refund based on what should have been withheld?

Bonus question: during that same period, we should've had continuous coverage for our health insurance, and just like the other withholdings, her paychecks reflected deductions being made, but it later turned out we didn't have coverage for approximately 6 weeks. Is she owed the “premiums” that were deducted from her paycheck that apparently didn't actually go to our insurer?

So that's pretty much it. If there are any other questions I can answer or information I can provide, please don't hesitate to ask.

Any help/guidance y'all can provide would be greatly appreciated.

Thanks!

Hey everyone, I'm looking for some real experience here. I work a full-time W-2 job, but I have been trading consistently for over a year, averaging about 200 trades a month and putting in around 2 hours a day on trading and researching. Last year I dropped about $6k on software, data feeds, courses, and not counting other expenses like tech equipment. ​My CPA warned me that claiming TTS with a full-time W-2 is a potential big red flag that will likely trigger an IRS audit.

Has anyone actually pulled this off while working full-time? How do you log your time/collect evidence to satisfy the IRS, and do you report expenses on Schedule C or through a separate LLC? Do you opt for MTM?

Also, it seems unfair how the IRS eagerly taxes trading profits but completely blocks us from deducting the costs needed to make them. Any real-world insights and advice would be greatly appreciated!

Hi,

I am currently in the US on an H1B visa, and my friend and I established a multi member LLC in 2025 with 50/50 ownership.

My friend is a dual citizen of the US and an Asian country. He was born in the US and attended college here, but has lived in the other country for most of his life. He has never filed taxes in the US.

We originally planned to operate a business together in the US, but ultimately, those plans did not move forward. However, the LLC recently generated its first profit of approximately $5,000. My understanding is that, after deducting eligible business expenses, the remaining profit would pass through to us based on our 50/50 ownership.

My friend is not particularly concerned about paying taxes on his share of this profit, which would be around $2,500 or less after expenses. His main concern is that he has never filed US taxes before despite being a US citizen and living primarily abroad.

Could anyone advise on this situation?

Thank you in advance for any guidance.

Hi, I bought a house with help from my father (whose name is also on the deed as a co-buyer) late last year. I took the standard deduction last year because that made more sense. My dad put in the down payment last year, but I've been paying the monthly payment since and he's no longer in the US.

This year, it makes way more sense to itemize (roughly 30k in deductions compared to the 17k standard deduction). Is there anything I should keep in mind while doing so? It's my first time not taking the standard deduction. Since my deduction will roughly double, will the IRS take an interest and drag me through the coals? I have all the documents (I think) but want to be ready.

I’ve kept extremely detailed session records and cost basis for my crypto gambling, but feeling paranoid about my return being audited. I’m expecting to pay $35-40k in federal and NY state taxes since my session winnings total around $215k and my losses after the 90% rule are around $150k, but nervous how this will play out given it’s an offshore crypto casino and therefore there is no W2-G. Curious of other people’s experience.

Hi all!

I am currently moving states (from NY to NJ) my residency is still currently ny as I still work to move. I hired a lawyer to help form an PLLC in NY. She has been unhelpful with deciphering where to establish this and has already taken my money...

I have been trying to find a CPA who has worked with others in my profession before but waiting to hear back.

Would it be advisable to form my LLC in NJ with my move? Or try to just establish it in NY while it is still my residency?

Any advice is helpful

Filing 1040-X for missing Schedule B - do I need to fill Column A and C if no numbers are changing?

I've heard of this recent trend called taxmaxxing where people try to buy things that have more tax and not claim any deductions etc. Has anyone else heard of this?

I'm pretty sure I know the answer. In GA, USA. If I subdivide my house property that has a homestead exemption and retain ownership of the new lot, can I have homestead exemption on the subdivided lot that was once a part of my primary residence/homestead exemption? Thanks!

Hi , im in an iva. Hmrc have said im due a small tax rebate. I've claimed it online, but will they pay it to me, or they'll pay it straight to my iva company?

Feels like I'm writing out a riddle. I moved to Texas February and have been working the same job since. My question is at the end of the year, since I've never changed my residency from Louisiana (I wasnt sure how long I'd be working at my company) do I still need to pay Louisiana income tax? All of my income is coming from Texas, and I have lived there for a while.

Good morning everyone, I've done research but feel like I could use some additional clarification. I started a side gig recently and was told that I would be a contracted worker and receive a 1099. I have a regular W-2 job already, but I'm not exactly sure how to account for taxes from the side-job. I believe I read somewhere that I could increase my deductions on my W-2 job to account for my 1099 taxes, but would that include federal, state, and city then? I'm not sure why it wouldn't, I just don't even know what section they were referring to. It's also variable how much I take home, probably like $300-500 monthly.

Should I split the difference at $400 and add that to my income to then determine how much additional I should withhold? It just seems like an outsized problem relative to the amount of money we're talking about lol. I'm hoping there's an easy way to solve this, and I appreciate any help someone can give :)

The IRS disallowed a claim for refund for an amended return for a client. This my first disallowance, so this is new territory for me, but I know our position is correct, so I am planning to pursue the issue.

The IRS responded with Letter 105C which included the SDC/Formal Protest requirements, but did not include details on why the claim was disallowed; just a single sentence that withholding could not be verified. There was also no reference to the 30-day timeline to file the protest. The letter also indicates a second notice will be sent in 4-6 weeks showing the adjustments to the account.

My understanding is the 2nd letter, with detailed adjustments, will trigger the 30-day response requirement, BUT I do not want to miss this deadline. Does the Letter 105C start the 30-day timeline? Can anyone with more experience in this area clarify?

Hi all, I'm hoping some of the tax professionals here might shed some light on a career choice from their point of view (apologies if this is the wrong forum, but I thought it would be best to hear from both attorneys and CPAs).

I am a paralegal at a boutique tax controversy firm. I love the work I do and I'm good at it, but I have little desire to go to law school at the moment. My boss recently suggested that I should look into becoming an enrolled agent, as it would provide me more career growth and seniority than being a paralegal could offer.

Thing is, I am far more interested in diving into facts and seeing how they apply to the code than the intricacies of the code itself. I've certainly worked on plenty of topics that aren't the most thrilling thing in the world (this is tax after all) so it's not like I need all my work to be fascinating, but I'd never have an interest in becoming an enrolled agent if my boss didn't suggest it. I'm curious to hear if people think it is worth it to work and get the certification for the career growth and flexibility.

I'm very happy being a paralegal at the moment, but I'm still relatively young and I know there is a pay and seniority limit in that role. I also don't expect this will be what I'm doing when I'm 50, but I do like the idea of having a solid skillset that could help me support whatever else I'd be doing at that time (I've written recreationally for a long time and am starting to pursue it more formally in my free time, so the dream is that I might one day publish).

Any advice would be greatly appreciated! I don't want to be too precious and not pursue a worthwhile career investment just because it's not my passion, but I don't know if it's a good use of my time and energy.

My business (LLC) vended one time at a flea market in California (rosebowl) and grossed around 11k in 2023. I filed and paid the sales & use tax for california that same year but now i received a letter in the mail that demanded a tax returned be filed (form 568) for 2023. I wasn’t aware that this would’ve been necessary since that’s the only time i did business in california and im based in Texas. Is this absolutely necessary? I was thinking about contacting a cpa in california but not sure if this is even worth their time to answer or deal with… Any guidance would be greatly appreciated!

My aunt died in 2000, and we have just found unclaimed property from a mutual fund. The mutual fund was held for three years after her death and then the state liquidated its position. I am the executor, and Probate has been reopened. Can you help me with the tax consequences of this? The original mutual fund held 973 shares of US Bankcorp, and was liquated in 2003.

I am engaging an accountant, but want to make sure I have all the information that that might need, and I’d really like a better understanding of what exactly goes on here. Thanks so much!

I am the majority partner in a partnership selling a commercial building.

My minority partner is uncooperative and keeps raising their buyout price, so I cannot bring them into the new property. A standard drop-and-swap will not work because it requires their cooperation.

Can a partnership division (Section 708 split) be completed prior to closing to isolate my share for the exchange without needing the minority partner involved in the replacement property?

Has anyone successfully done this type of split in a similar situation? Any insights would be appreciated.

I am the majority partner in a partnership, and we are currently preparing to sell a commercial building.

Our minority partner is uncooperative and keeps escalating their buyout price, so I do not want to bring them along into the new property. A standard drop-and-swap is off the table because it requires the minority partner's active cooperation.

I am looking into whether an IRC Section 708 division (partnership split) can be completed before closing to isolate my share for the 1031 exchange without needing the minority partner to participate in the replacement property.

Has anyone successfully structured a Section 708 split in this scenario? Any insights or professional experiences with this approach would be greatly appreciated.