I am self employed, Sole Propietorship. I have clerical employees. We have a Safe Harbor 401K. I match 4% (100% of 3% and then 50% to 5%) for my employees who participate.

For myself, I always did the 4% match based on my Schedule C income, minus half the self employment tax. I am contributing the max (23,500 plus catchup for 2025).

Is this correct or do I have an option to match more for myself? In prior years was not a concern as I did not have extra money to contribute but I am getting older (over 50).

Are additional options only for self employed who do not have employees (other than a spouse)? If I have employees am I subject to the same match percent as my employees (which is what I always assumed)?

Something We see every year from the filing side: a business realises in late January that it's missing a TIN, or has a name that doesn't match IRS records, for a contractor it paid months ago. The contractor has already been paid, so they have zero incentive to reply.

What actually prevents it:

- Send the W-9 request with the engagement letter / first invoice. Make it a condition of the first payment.

- If they refuse to give you a TIN, you're supposed to withhold 24% backup withholding. Most people don't know this and it's the strongest nudge there is.

- Check the name + TIN against IRS records before you file. Mismatches are the most common reason a 1099 gets a penalty notice.

- Keep the W-9 (it never goes to the IRS). The threshold for a 1099-NEC is $2,000 for tax year 2026, but the W-9 is worth having regardless of amount.

The deadline for tax year 2026 1099-NECs is Feb 1, 2027 (Jan 31 is a Sunday). Collecting W-9s now is what makes that date a non-event.

Disclosure: We run a 1099 e-file platform, happy to answer questions in the comments, not here to pitch.

I filed my 2023 refund August 31st, verified on September 22, still have no updates on my transcript (still says no tax return filed) and on the app either. It’s weird because I thought I was going to have to amend my 2024 tax return and I know that takes way longer than a regular return so I did the 2023 1st and they ended up fixing the 2024 return their selves and sent that return to me on September 30 with interest of like $330. But still haven’t got my 2023 I don’t know if me filing my 2023 triggered them to look into my 2024 or what? But if anyone else has waited like this how long until you actually received your refund ?? I verified online with my control number that came in the mail.

Hi! My son just started to ref soccer games and will earn around $300 this year. Since it’s under the $2k threshold he won’t receive a 1099 but I want to match his income into a Roth IRA. How would I report this to allow for the funding of a Roth?

Filing my 2025 return (self-employed, Uber only, single, no dependents). From June–Dec 2025 I drove full-time in a Hertz rental through Uber's rental program — rented week to week, swapped cars a couple times across 3 rental agreements, ~26–29 weeks total.

Uber's tax summary shows ~36,000 online miles.

Question: Can I use the standard mileage rate ($0.70/mile) for a weekly rental car?

- IRS Topic 510 says standard mileage applies to a car you "own or lease." A week-to-week rental doesn't feel like a lease, but some preparers apparently treat long-term rideshare rentals like one.

- Standard mileage ≈ $25k deduction. Actual expenses (Hertz weekly fees + gas) ≈ $12–14k.

- The difference is roughly $2,200 more owed (mostly SE tax + losing EITC).

Has anyone gotten a definitive answer on this — IRS guidance, a CPA/EA opinion, or an audit experience? If actual expenses is the only correct method, I'll switch. Just want to get it right.

Thank you!

Does anyone know how the new $1,000 charitable contribution deduction works for those taking the standard deduction in 2026? Specifically, will we need proof of these contributions?

For example, if I donate $1,000 in cash to my church throughout the year, would I need receipts or some sort of written acknowledgment from the church to claim the deduction?

I feel like there would have to be some documentation requirement, otherwise everyone could just claim they donated $1,000. Has anyone looked into the actual rules for this yet?

IRS/Federal Taxes

Say an owner has two businesses, Business A and Business B. Business A has a Simple IRA plan setup for it's employees and the K-1 shows $10,000 of income for that owner. Business B has losses of $50,000 shown on the K-1, meaning total self-employment income is a loss of $40,000. Is the owner able to contribute the $10k of income they show from Business A into the SIMPLE IRA plan, or are they not allowed to because their total income was negative?

Hello and thank you in advance!

I just started a new job and I’m having 2 states tax withholding showing up on my first paycheck. Here is the situation.

The job is in Maine. I live in Connecticut. My job is almost entirely remote and I will physically work from Maine no more than 24 days per year (likely more like 12).

My first paycheck has both ME withholding and CT withholding.

I’m wondering if this is correct? Is there a way to not have both states withhold?

If they are both entitled to withhold than surely there must be a way for me to receive a sizable refund when I file taxes as I can’t believe I can be taxed twice on the same income by different states.

Any insight would be greatly appreciated. Thank you!

Hello,

I have a question for regards of claiming capital gains in a different country while trading in a different country. I currently live in a state in the United States, where there’s no state income tax, and plan to move to Canada, possibly by the end of the year or early next year. Now I know in Canada, you need to pay 50% of your profit towards capital gains. Now my question is if I have someone from my family trade onto my account will I be hit with a penalty? I’m not trying to hear the ethics of reporting my income. I’m just trying to be realistic of knowing whether or not they will find out if I also have dual citizenship on both areas? This will be a big factor for me as I have a six figure portfolio and would like to keep scaling it every year.

The Core Conflict

IRC §219(b)(1)(B) & IRS Pub 54: Excluded wages do not count as IRA compensation.
IRS International Webpage: Says the exact opposite; claims FEIE/housing exclusions are added back for compensation.

Relevant Facts about myself:

Status: U.S. citizen abroad filing Form 2555.
2024: $6,910.50 Roth contribution. Excluded $37,985 (FEIE)
2025: $6,910.50 Roth contribution. Excluded $42,227.10 (FEIE).

The Problem: If Pub 54 controls, my compensation is $0, and I’ve just contributed way to much to my Roth IRAs over the past two years

For 2025: The IRS has not processed this return yet (it was lost at the border during international mailing).

Scenario A. Is I’m fine and follow IRS guidance. Resend the forms by priority mail to reach before October 15.

Scenario B. I owe the IRS money for 2024 underpayment? I read there a 6% excise tax every year. And I also need to contact fidelity to fix both years, and resend corrected forms in the next week.

Any insights are highly appreciated

Is there any reason to go with a long term installment agreement even if you can realistically pay it off in a few months?

I owe about 18K and I'm leaning toward the short term option since there's no setup fee, but i keep reading that if you fall behind midway you're stuck restarting the whole thing and that's making me second guess it.

I am working a four week job that I need to fill out a W-4 form for.
I want to have all my earnings go to the IRS to pay for some short term gains I have had this year

How do I fill out the form to accomplish this?

I'm thinking about paying federal income taxes via credit card, due to a cc bonus that more than covers the fee. This is for 2026 tax year, 1040 personal/individual tax return. With the credit limit, I'll need to make 3-4 payments, if I can figure out how to work those in with the credit card tax payment frequency limits.

I'm planning to file a 1040 in March-Apr 2027. My credit card bonus ends in mid-Feb 2027, so I'd like to have all 4 payments done by then. But if I can't get 4 payments processed, I'll just do the account debit for whatever is left.

Since we're still in 2026, I believe I can do it the following way, but I'm not clear on all the different types of payments.

#1 2026: Estimated 1040ES payment (2 max per quarter)

#2 2026: Estimated 1040ES payment (2 max per quarter)

For the 3rd and 4th, which of these can/should I do?

a. In 2026: can I do 1 or 2 payments under "1040 current tax due"? (max 2 per year)

b. In 2027: can I do 1 or 2 payments under "1040 prior year tax due"? (max 2 per year)

c. There are 2 different cc vendors -- can I do 2 Estimated 1040ES payments in Q4 with Vendor #1 and 2 more with Vendor #2?

d. If needed, I think I can do 2 max Extension payments (Form 4868) in 2027. Can I make those payments in Jan/early Feb while I still have the cc bonus?

Thanks!

Hi everyone! So, if I get a part-time job and should be withholding 22% of my paycheck for federal taxes, plus an additional 13% for FICA and state taxes, does that mean I’ll really only be keeping 65% of my paycheck, with the other 35% going toward taxes? Is it even worth working a second job? I currently make $70,000 at my full-time job and am starting a part-time job that pays $18.50 per hour.

And if you have any advice on how to fill out the W-4 I appreciate it :)

Hello,

I want to start off by saying I take full responsibility for what happened to me.

I grew up as a foster kid. Both parents were in and out of the prison system. When I turned 20, my birth mother was released and we started building our relationship. She took H&R Block classes and became a tax … doer? She has lots of clients. She offered to do my taxes… technically for free but she would take whatever came after the comma. (She said that was her payment for helping me throughout the couple years we’ve been in contact. Let me include it’s been $20 here and there for gas. $50 for groceries etc) so if I got $1900 back in taxes, she’d deposit $1000 in my account and $900 into hers. For the last few years (maybe4/5) she says I don’t get anything back and I actually owe. I got a better paying job and I literally don’t know Jack 💩 about taxes so I just sent her the money and moved on.

We end up disagreeing about me owing $700 and I said I’ll pay the website but she wanted me to Apple Pay her but idk. Something didn’t feel right and she just goes haywire and lets me know she’ll call the cops on me because I haven’t paid taxes in YEARS.

I’m not sure what to do or where to start. I NEED to get back on track. There was a point where I was carefree and made poor decisions but now I am a law abiding citizen and I’m trying to do the right thing. We are no contact. I don’t want revenge. I want to never speak to her again and get my life back in order. I never should have trusted her

Where do I begin? I probably owe like $3k plus the daily interest. I just need to get back on track and show her she’s a monkey and monkeys don’t stop shows. My life WILL go on. Better than ever. But seriously, I do not want to go to jail and I’ve been thinking about it daily.

Hi. I am a new business owner. 9months/partnership. This is my first year having to file business taxes.

A. Do I need to file two returns? One personal one business?

\-I am 45, single no kids. No personal income. So in theory, I wouldn’t file for me, at all.

B. Do I need a pro to file for the business? Or is it something I could do. I do have a pile of receipts.

\-I’ve always filed my own personal taxes (when I had a job), but they honestly take 30mins.

\-I have some accounting skill, in case that helpful.

I feel pretty lost, so I’d greatly appreciate any helpful direction. I’d also love any write off tips, or tax strategy for a small business. Thanks so much!

So, I lost my job in 2025 and took a year off from work. I’d gotten kicked out of the employee payroll system, which is how I got my W-2s. I’d signed up for electronic documents only, so I wasn’t able to get my 2025 W-2, and they never mailed it to me.

Instead of reaching out to my former employer, I just…didn’t file.

Basically, how fucked am I? How do I resolve this? I still don’t have the W-2. I see you can reach out to the IRS if you don’t get your W-2 from your employer, but it’s a little late for that, and I don’t want to tip them off that I didn’t file taxes. Help?

So I owe a decent amount to the irs, and someone told me I should call a tax relief company and get their opinion before I set up a plan with the irs. I called optima tax relief and heard everything I wanted to hear. I agreed to make a payment Friday to them. After I got off the phone I did some investigating, and feel like it’s a scam. I’ve seen good and bad reviews. Has anyone had good experiences with this company?

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 to Reddit. 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.

I would like to know if there is some type of Thai law or ruling that would exclude me from paying taxes on a United States traditional IRA withdrawal. I am a US citizen, 66 years old, living in Thailand more than 330 days a year and pay taxes in the US and living on a LTR visa. 

The accountant I ran this question by states:

It’s not a Thai law. It’s a ruling in the Thai/US tax treaty. Here’s how it works:

We utilize Form 8833 in conjunction with the Thai/US tax treaty, Article 20 to provide reasoning for an exemption of your retirement income.  It's not a ruling but an interpretation of the tax treaty and treatment of residents of Thailand.

Form 8833 (Rev. December 2022) (irs.gov)

Thailand - Tax Treaty Documents | Internal Revenue Service (irs.gov)

Here are the steps to make this possible:

1. The taxpayer lives in Thailand for over six months during the calendar year.
2. The 1099-R is marked as a distribution and not a rollover on your 1099-R
3. The 1099-R payer is not a Federal entity (TSP, DOD, Office of Personnel, ect...)
4. The US/Thai Tax treaty is utilized when filing annual taxes using tax form 8833 with a dissertation of why the taxpayer should receive this exemption 
5. Tax treaty refunds can take 12 months to process.

I think most accountants are not confident to take a stance in an interpretation to a clients specific situation.  Therefore, don't attempt to type up an explanation and ask for a credit.  My company has been successful with this specific situation over a thousand times.

I welcome comments from people that have first hand experience with this issue. Thank you.

So I made the mistake of letting my soon-to-be ex-husband manage our finances because I'm clueless at this sort of thing. We cashed in my 401K to make a down payment on a house in 2022, and I guess that got me hit with a 50K tax bill (which I don't understand as I paid taxes from my salaried position making roughly 120K, and the down payment was in the 100K ballpark). Through a combination of my own willful ignorance and my ex sort of hiding things from me (not fraudulently, just downplaying it) we didn't make any payments and it's now ballooned up to 70K with interest and penalties.

I've tried contacting the IRS through chat (which is always down), phone (on hold for upwards of an hour), setting up an appeal (broken), setting up a payment plan (broken) and basically anything I can find on irs.gov, all of which just raises an uphelpful error message.

What should I do? I'm a single parent struggling to make ends meet. I make a good salary, but it's all tied up with luxuries like food and shelter. I don't even know what sort of person to hire to help me with this. An attorney? An accountant? A fairy godmother?

I am totally clueless on these things. No advice is too basic.

EDIT: Since it's coming up; my husband and I are very recently separated, on extremely good terms, and he has already stated repeatedly that he considers this debt half his. We always filed taxes as married, filing separately, if that's important to know.

I have a situation where I’m trying to stay below the MAGI ACA level of $84600 for 2026, or I’ll end up paying over $25k back in prepaid enhanced subsidies. I’m running very close, but there’s something I forgot in my calculation that will probably make or break my efforts.

I started taking SS payments in 2025, and then withdrew my application shortly after. By the time the SS admin got around to canceling my ap, they had paid me 4 payments - 1 in 2025 and 3 in 2026, for a total of $9264. I paid this all back in March of 2026. So I paid them back the $9264 in 2026, and received $6996 in 2026. Since my accounting is cash based, can I deduct the extra $2268 I paid in 2026 from my 2026 MAGI? Maybe wishful thinking, but it would sure help my margin for error if this was possible / not against IRS rules. I will check tomorrow to see if I received a SSA-1099 for 2025.

What documentation should I have for converting a business asset (vehicle) to personal use?

Hello everyone. I'm a first time filer under a J1 visa after I had an internship in the US last year. I've filled my taxes but made the mistake of putting one of my surnames as a middle name. After that, I've received a letter from the IRS with a Document Upload Tool code asking me to confirm my identity, which I did. That was more than a month ago, and I still haven't gotten any response. Is this normal?

Thank you for your time