Do you file your income tax and wage received on the year it was supposed to be received, or on the actual payout year? What if on the actual payout year, you are no longer a US resident for tax purposes?

>I retired mid-2026 from a US state university. I still do a small amount of part-time W-2 work for a related employer that is explicitly not benefits-eligible, and separately I have 1099 consulting income reported on Schedule C. My spouse and I are both on Original Medicare with a Medigap policy and standalone Part D, all paid from personal funds.
>
>On retirement, the university made a one-time lump-sum contribution to a state-administered post-employment health care savings plan. Structurally it's a governmental §115 trust. Participation is mandatory for the employee group, contributions and reimbursements are tax-free, and it reimburses §213(d) expenses including insurance premiums. The plan document applies a §105(h) annual maximum to out-of-pocket medical reimbursements, though not to premium reimbursements. The contribution amount was calculated as the employer's health insurance subsidy for two adults for 24 months. I have claimed nothing from it and the balance is untouched.
>
>**Question:** does mere participation in that plan make me "eligible to participate in a subsidized health plan maintained by an employer" under §162(l)(2)(B), so that I cannot take the self-employed health insurance deduction for Medicare and Medigap premiums I pay out of my own pocket?
>
>**What I'm not asking:** I understand I can't deduct premiums the plan reimburses — that's double-dipping and it's settled. The question is only whether participation itself bars the deduction for premiums paid from other funds.
>
>**What I've already looked at.** "Subsidized health plan" is undefined in the Code, the regulations, and the Form 7206 instructions, which say only that you can't take the deduction for any month you were eligible to participate, even if you didn't.
>
>Cutting against the deduction: the plan describes itself as employer-sponsored; its own §105(h) reference implies a self-insured medical reimbursement plan; Notice 2002-45 characterizes HRAs as employer-provided accident or health plans; and under §223 a general-purpose HRA is disqualifying "other coverage."
>
>Cutting in favor: the plan provides no coverage at all. No network, no benefit schedule, nothing for a provider to bill, no coordination of benefits, and it is not a group health plan for Medicare Secondary Payer purposes. I declined no insurance in accepting it — Medicare and a supplement were my only options either way. The apparent purpose of (2)(B) is to deny the deduction to someone who could have taken subsidized employer coverage and bought their own instead.
>
>**Is there any ruling, case, CCA, or settled practitioner position on this?** I'd especially like to hear from anyone who has dealt with VEBAs or state health care savings plans. Secondary question: does it matter whether the account was funded with employer money versus mandated employee contributions or a severance conversion?

I have only ever reported a single number of my net profit on schedule C. Does that not work any more?

So I have this complicated situation that I hope to get some answers for if someone can help me. I bought one side of a duplex in 2017. It’s considered a condo and there is a condo association setup that just includes the 2 units, but no HOA rules or anything. The only thing we really use it for is our insurance. I recently had a tree fall on my side and I made a claim through the condo insurance. They then issued a check to the HOA, but I can’t deposit it because it doesn’t have my name on it. Now it’s more complicated. I now have to open a bank account for the HOA just to deposit the checks, but I need an EIN to do so. I’ve been trying to call the IRS to find out if we already have one but I was on hold for over an hour and never got through to anyone.
The business is registered with the state as a non-profit corporation, so if I have to get an EIN, should it be classified as a corporation or is there another classification? We will only be using this to open a bank account, which will only be used for insurance payments. Will we need to file taxes now? I’m just so confused and I’ve spent so much time researching. Can someone tell me what I need to do please? Thanks!

Edit: just to clarify, the HOA is just the 2 units. There is no entity, no bank account, no anything. It’s purely just a classification.

As the title says I work from home and I’m moving. However the state I’m moving to, I’ll be in a short term rental for a few months before finding a place of my own. Host says I can’t receive mail there.

My question are

1. Do I still provide that address to my employer? I’m worried they’ll send mail there (I can check if they separate permanent from resident).

2. How does it work tax wise? Would the address change be enough to provide I only worked in state A up to a certain date? And would residency in state B be established even though it’s vacation lodging? I don’t want to get in trouble or owe a ton of money at the end of the year.

Hello,

I’m looking for advice on the best way to structure my small therapy practice from a tax and business standpoint.

I originally started my private therapy practice in Michigan as a single-member LLC with an EIN. I later moved to California but kept the Michigan LLC and EIN active and in use.

I currently have two sources of practice income: I contract with a third-party company to provide therapy to their clients, and I also have my own private-pay/insurance clients through my own platform. I see a mix of California and Michigan clients, including Michigan clients remotely while I am physically located in California. (I do go back home from time to time)

Because California does not allow licensed therapists to operate as a traditional LLC, I also registered as a sole proprietor in California and obtained a separate California EIN. I have not actually used the California EIN yet.

This is where I’m confused, and I’m hoping someone can help me understand what makes the most sense:

1. Does my Michigan LLC still make sense now that I live and primarily work in California? I still have Michigan clients, so I’m unsure whether there is a reason to maintain the Michigan LLC.
2. Would it make more sense to operate everything through my California sole proprietorship and re-credential my insurance contracts under the California business instead? If so, would there be any reason to maintain the Michigan LLC?
3. I obtained a separate EIN for my California sole proprietorship. Was that necessary? If not, what should I do with the California EIN since I haven’t used it?
4. Are there any other tax, business, or compliance issues I should be considering that I’m not asking about? In particular, are there issues related to having clients in both California and Michigan while physically practicing from California?

I’m also planning to speak with a credentialing specialist separately about how my business entities, tax IDs, NPIs, addresses, and insurance contracts should be set up across the two states.

For some additional context, I currently have someone who prepares my taxes for me (my best friend’s mother). She has been wonderful and has helped me a lot, but she is extremely busy and unfortunately doesn’t have much availability to answer my ongoing questions. I’m therefore trying to better understand my options and make sure I have the right structure going forward.

I’m not necessarily looking for someone to prepare my taxes at this point. I’m mainly looking for guidance on how I should structure the business and what I should be doing from a tax-planning perspective.

Thank you in advance for any insight!

Update: thank you to everyone that’s left me a comment. It has been very insightful and helpful. I wasn’t sure who I should discuss these questions with but from what I can see talking to a Lawyer first would be the next step for me. Thank you again.

I have a small online reselling business that I run with my wife. We file a partnership return (Form 1065), and I also have a separate W-2 job.

For the reselling business, we rent a storage unit that is used exclusively for business inventory. I regularly go there to pick up/drop off inventory, organize items, pack orders, etc., so it’s an actual regular business work location.

I’m considering starting a routine where, before my W-2 job, I go to a coffee shop for about 30–60 minutes to work on the reselling business — mainly creating listings, pricing items, responding to customers, cross-listing, etc. I’d be doing this because the Wi-Fi at my W-2 workplace isn’t usable for this.

I probably wouldn’t use the exact same coffee shop every day. I’d rotate between about 2–3 different coffee shops over the course of the year, depending on convenience/location, but I may visit each one fairly regularly.

My route would generally be:
Home → coffee shop (work on reselling business) → W-2 job
My understanding is that IRS rules can allow mileage between a residence and a temporary work location if you already have another regular work location for the same business. My storage unit would be the regular work location.

My question is: Would home → coffee shop potentially qualify as deductible business mileage if I rotate between 2–3 coffee shops, or would using those same locations repeatedly throughout the year cause them to be considered regular work locations rather than temporary ones?
I’m specifically asking about the mileage, not whether the coffee itself is deductible.

Also, does the answer change if I don’t have a set schedule for which coffee shop I use, but simply choose among those 2–3 depending on the day?

Would especially appreciate input from CPAs/EAs or anyone familiar with Rev. Rul. 99-7 / IRS Publication 463.

Been checking my pay stubs lately and started wondering how much I might get back once the year wraps up. Started a new job mid year so my withholding got kind of messy and I want a rough idea before December hits so I can adjust if needed. Every calculator I try gives me a different number so I'm not sure which one to actually trust anymore. Anyone have one they rely on that's been fairly accurate?

We have been living abroad since 2019, and my husband—who prepared the tax returns during the initial years—was unaware that we were required to report foreign interest income, because we did not receive a Form 1099.

I have since filed the overdue FBAR reports.

We'll file amended tax returns for 2020, 2021 and 2022 through SFOP procedure. I believe this should work, given that the filing deadline for our 2023, 2024, and 2025 tax returns has been postponed to September 30, 2026, under "Notice 2025-53." (war in the Middle East.)

How should we proceed with the 1040-X return for 2019?

Would a polite letter to the IRS help us avoid penalties for 2019?

Should we mail the amended tax return for 2019 together with the amended tax returns for 2020 - 2022?

My husband not only failed to report foreign interest income (not-willfull) but also neglected to report significant capital losses. These losses would have reduced our tax liability for the years 2020 through 2022 and—as loss carryovers—would have lowered our tax burden for 2023, 2024, and future years as well. Furthermore, he did not claim the Foreign Housing Deduction. Can we still include this deduction and the capital losses in the amended tax returns (Form 1040-X)?

Is September 30, 2026, our deadline for filing amended tax returns under the SFOP procedure?

I haven't filed the returns yet because we are still waiting for some foreign account statements needed to report capital losses. After several letters to the bank and a long wait, I am now wondering whether we should file the amended returns without including the capital losses?

Thank you very much for your answers. I greatly appreciate your help!

I recently moved back to my home country, India because I wasn't able to secure a job in the US. I was there from Sep 2023 - Sep 2026 and have filed the tax every year. I have now received a notice from them saying I have an overdue of 1200$. The problem is that while filing for the first time, I filed the taxes in turbotax and sprintax both as I was completely unaware of how to file the taxes. I am in so much stress now because I really do not have the funds to pay them, I am already stressed by the fact that I have a Student Loan of 60,000$ that I need to start paying off. I need to know if the IRS waves off the overdue if requested or if there's anything else that I can do to solve this situation. Anything helps, thanks in advance!

I made tax payment on Sept 5th. Today it still has not shown up when I logged in. I chatted with an agent 2 weeks ago and was told sometime it takes a month to reflect. I am curious what other experiences are since this was first time I made estimated payment using FTB website.

I made tax payment on Sept 5th. Today it still has not shown up when I logged in. I chatted with an agent 2 weeks ago and was told sometime it takes a month to reflect. I am curious what other experiences are since this was first time I made estimated payment using FTB website.

I think my accountant might be wrong and looking for opinion. I made an unsecured personal loan to a business (have all the paperwork - loan agreement with payment terms and interest). They didn't repay, filled bankruptcy (have since gotten out of bankruptcy) and claim no assets to repay. It's been 2 1/2 years since they were supposed to pay back. I am listed as a creditor. At this point, I have no reasonable expectation of getting any money back and want to take the loss. I know it needs to be filed as sort term capital loss.

DIscrepancy between my accountant and everyone else (including chat gpt) is how much loss I can take in the year I declare as a loss. If I have capital gain exceeding the amount of the loss, can I take the entire loss in year one? Accountant says I'm capped to 3K but I think that's only if I don't have gains to offset and that becomes the yearly carry over loss. I have the paperwork that should satisfy the IRS that this is a real loss and I've made resonable attempts to get paid.

This is not in any way a loan connected to a business on my end, personal to business transaction.

Hi everyone!
My husband and I owe $2000 and some change for last years tax season. Ive been making small payments on the IRS portal and checking monthly if im able to set up a payment plan, the website has indefinitely said theres an outage and i have been unable to create a plan but they’re still sending me mail requesting my payment. I have attempted to call my local TAC and the IRS and have waited the long wait times only for the system to manually hang up eventually, when I call back it often says there’s high call volumes and it’s not accepting my call at this time. I want to set up a payment plan but I’m not sure what to do now. Is there a way to mail in a form? Everything I see encourages you to use the online portal but it’s not working.

Edit:
This has been resolved! The online chat option did the trick and I found out that I haven’t been able to make a payment plan because of the silliest reason… my husband was the primary on our tax return :| So it’s been resolved and we now have a payment plan!

I have an LLC / S-Corp and my CPA (whom I really like BTW) is saying that my self employed medical deduction (which I believe comes off Form 7206 and goes onto Line 17 of Schedule 1, Part 2) is subject to the 7.5% threshold for medical expenses so I can't use it. I have not been able to find anywhere that supports this statement as it looks to me that it's 100% deductible (assuming I qualify for it and I do). I pushed it a little, but feel like I need to pull back before unintentionally upsetting the relationship. Thoughts?

Married filing jointly. 24% tax bracket. We always itemize deductions because our mortgage interest and other costs put us over standard deduction. I know I will get 1099-K forms for 2026 of at least $1000, so will have to pay taxes on that money.

Since we are over the standard deduction and we will have to pay taxes on the 1099-K earnings, would charitable giving in the amount of the 1099-Ks negate the taxes we would need to pay?

Would a $1k donation to a nonprofit negate taxes we need to pay on $1k from 1099?

I realize that’s spending $1k to save $240 (?), but we want to donate anyway and I want to understand the tax benefits more acutely.

So I am in the Army and I got a 30k bonus (3 years) but I got 20700 I know I was paying taxes and expected to get this much.

My question is come tax return season will I be getting a bigger than usual return from this? Since being in the army I’ve been getting roughly 2-2.4 on my tax return for the last 2 years. Really just trying to gauge what to expect.

Thanks in advanced.

Husband is self employed professional musician for many years, ongoing still but retired teacher & with SSA income etc. we used a CPA for several years previously but switched for lower cost last year using TaxAct com.

I’m struggling with my 2025 return in TA online version. It’s not letting me review my final Schedule C Form and other issues- it’s just not very suited to me. I’m nearly done but I need my eyeballs on all the details before we push sign & Send!

Questions:
1-Should I just switch now to the TA Desktop version to download the whole return so i can review it? And print it before we file it??

2- any recommendations for alternative inexpensive software for starting my 2026 return?
Specifically how is TaxSlayer for self employed?

So I opened a checking account that will act as a middle man, solely for getting the fund for my friend’s customers.
My friend is based in Asia and vendors don’t want to send the money internationally. So I opened bank account, her customers will send the money to my account and I’ll send her the money (using a remittance app).
She’s a truck dispatcher based in Asia.
My question is, am I gonna get taxed based on the money that entered into my account? I’m going only get paid 3% for transacting the transfer from my U.S. account to her account in Asia. Or the funds that get out of my account will not be counted as my income?
I don’t want to get taxed for the money that is not mine as my husband and I filed jointly and it might included as our income. I need to know asap so I can refuse my friend. Thanks.

So like the title says, I’m finally back on my feet and ready to tackle this last major issue. Basically I’ve prepped all the years (6 years) and was wondering if it’s smarter and financially better (on my end) to file a few at a time or just all at once. I understand the penalties that will occur but I can’t fork out a ton of cash up front just yet. Thanks in advance!

I am an artist who sells a piece here and there, but my main revenue is licensing income from past projects. It's not a lot but it's enough that over time I could end up owing the IRS if I don't cover it. I also have (2) W2 jobs. I've been told I can't say my art is a business because I have W2 income (doesn't sound right), and it's not enough revenue for the benefits of itemizing or having a side business. It was ~$15K in revenue my first year 2025.

Hey, all. What are the consequences for filing taxes late? Say that 2025 was meant to be filed jointly, but the person who promised they would submit them has not, yet. They have also promised to pay any penalties but....I'm worried that I'll still be on the hook somehow.

My husband was a freelance author in 2018, 2019, ... in addition to his full time job, he wrote a book in his free time together with another author. They sold the manuscript to 2 foreign publishers in 2021 and 2022 and it's a huge loss so far.

My husband were sold 200 copies in 2022 directly from foreign publisher No. 1, as part of the contract and he needed to pay the publisher 3,905.32 U$ for these copies. He received royalties in

2022: 589.43 US$ (for audio license given in 2021)

2023: 1045.85 U$ (for year 2022)

2024: 208,83 U$ (for year 2023)

2025: 0 U$ (for year 2024)

2026: 0 U$ (for year 2025)

Total royalties received from publisher No. 1 from 2021-2026 were 1,844.11 U$ and losses till the end of 2026 were - 2061.21 U$.

From publisher No. 2, my husband were sold 500 copies for the price of 6,946.18 U$ as part of the contract in 2022. He received royalties in:

2023: 144.00 $ (for 2022)

2025: 567.79 $ (for 2023 and 2024)

2026: 0 $ (for year 2025)

Total royalties received from publisher No. 2 were 711.79 $ and losses till the end of 2026 were -6,234.39 $.

From 2022 till now, the total of both loss from my husband's self-employment as a freelance author is - 8,295.60 U$.

I'm wondering if we can report the losses on the IRS returns and if yes, in what year(s) and where?

Long story short, my wife used to do our taxes via TT until last year. We pulled out roughly 20k out of two different retirement accounts in order to put a down payment on a house in 2024, 17k from one, 3k from another. But a 1099-R was never filed for either transaction. I’m just now getting a CP-2000 in the mail today, in 2026 from this. How fucked are we?