For you business owners, payroll taxes/withholding and sales taxes are not your money. They are government money that you are holding temporarily. Don't turn a civil issue into a criminal issue.

Original story is from the Seattle Times. Non-paywall link.

So, here's the gist: So far this year, I've made a little over 1200 dollars off of YouTube ad revenue. In January, Google will send me a 1099-MISC, but they don't withhold taxes for you, so I've been setting aside 30% for when I need to pay it..... But how the hell do I pay that at all to both Uncle Sam and the state of Indiana?

Do I wait until January, or should I be doing that now?

Anyone else have or had issues with making tax payments either estimated or income tax payments online that then sit in pending status and never actually go through?

I’m an Italian citizen living in the US (on a visa authorized to receive the following kind of money) and a US tax resident (Massachusetts), roughly in the 22% federal bracket. I’m receiving a €1,333 merit prize for doctoral research from an Italian scientific foundation. No services were performed in Italy, and I wasn’t there when it was awarded.

The foundation offered two options: (1) apply the US–Italy treaty, which requires an IRS residency certificate (Form 8802 → 6166, $105, 45+ days), and they’d pay only after receiving it, or (2) withhold 25% Italian tax as a final withholding and give me a CU (Certificazione Unica, i.e., a report) to claim the credit.

Questions:

1. Which treaty article applies to the prize, 21 (students/trainees) or 22 (other income)?
2. If I take the 25% withholding instead of using the treaty, is the Italian tax creditable on Form 1116, given the treaty may have exempted it?
3. Is the treaty route worth the $105 and the wait for this amount?

It finished worthless and fits the definition of a crypto scam for that form but wouldn't it be simpler for me to say I sold it for $0 and just report it on Schedule D?

I was just receiving SS last year, so I didn’t file. This year I took a part time job that will only amount to about $7000.
I assume I should file?
What to put in the last year’s income box on the forms?

Received a blank 1096 form from the IRS to be filled and returned for 2026. Is this just preemptive for those that have filed by paper last year?

I moved to Thailand in the first half of January 2026 and will be moving back to California at the end of November 2026. I was employed most of the year and recently started working as an online tutor. By the end of the year, I will have made around $8,000 for the whole year. I also haven't had medical insurance for the year, so I'm sure I'll owe something for that. I've been trying to figure it out, but I'm a bit confused. Any helpful information would be much appreciated.

I've helped a client form a GRAT. Estate attorney drafted the docs. Net zero gift value. I've heard that some practitioners file a 709. Others don't. The estate attorney kind of shrugged and said to do whatever we want.

What would you do?

I setup a GoFundMe to support the cross country team at a local high school. I went to setup the beneficiary with the school but they don't have the ability to input their account to receive withdrawals. I didn't want to withdrawal and pay the school from my own account but it is looking like I may have to. What are the tax implications of be accepting the withdrawal from the GoFundMe and then donating the entire amount myself? Any advice on how to best handle this situation?

My adult daughter, who is 21, has lived with me for 3 years, has never held a job, and does not have any form of income. Can I claim HOH instead of single? And where it's says multiply the number of dependents by $500, I put $500 (I know, obvious.) My job is making everyone fill these out so thank you in advance.

*edit. I forgot to mention she's NOT a student.

Hello everyone.

I left a company and I am required to pay back an amount due to a breach in the contract of time in position. I was given $7500 for relocation, $1250 for not using all of my moving assistance allowance, and rental reimbursement for the location move. I am currently trying to get this waived but I don’t think it will happen. Does anyone know how much of any of this could be deducted from taxes since I am paying back?

Thanks.

(United Kingdom) Good evening, I’m an 18 year old currently working a role seeing me work roughly 50 hours a week and on PAYE payroll, however I am also self employed and earn money elsewhere approx £1.5k extra a month.

As of my knowledge, post April 2027 I will have to file a self assessment, this will include stating how much money I have earned total via paye streams and self employed streams alongside accompanying costs related to my self employment.

It is as simple as that ? HMRC should then tell me what I need to pay when I tell them how much I have already paid via my PAYE job and how much extra profit I have earned during the tax year.

What else would I need to consider and be aware of ? Many thanks it will be my first time so want all the advice possible thank you very much

I have a few friends who have been doing extremely well with sports betting lately, making five figures in profit over the past couple of months.

They've told me they follow a strategy where they keep individual wins below $5,000 and withdrawals below $1,000 because they believe it prevents sportsbooks from issuing a W-2G. Don't quote me on the exact thresholds, but that's roughly what they've explained to me.

Because of this, they're planning on not reporting any of their gambling winnings when tax season comes around.

They've been on a pretty crazy winning streak lately, and I've genuinely been thinking about copying some of their bets. But the tax situation has me curious about how risky what they're doing actually is.

If someone makes $50k-100k+ in annual gambling profits without reporting any of it, how likely is the IRS to actually catch that? Do sportsbooks still report gambling activity even if no W-2G gets issued?

I'm especially curious whether this is something the IRS realistically catches and pursues, or whether people sometimes get away with it for years before anything happens.

Would love to hear from CPAs, tax professionals, or anyone with firsthand experience dealing with gambling taxes and IRS audits.

I'm asking because I've considered copying some of their bets, but I want to understand the tax obligations before getting involved. I'm not looking for ways to avoid paying taxes.

I have a question for the upcoming tax season. In 2025 I was living in Ohio, I started a new job in Michigan right at the end of December. We did not officially move until February 2026 so I was earning income in Michigan for 2 months while technically residing in Ohio. My job only ever withheld Michigan state taxes from any of my paychecks. Will I need to file both a Michigan and Ohio tax return for 2026?

Thank you in advance

This year, October to be exact, I started selling art prints at local fairs. I am a sole proprietor and havent turned a profit yet. I think I will make a couple hundred at the end of the year. And I dont expect to make above 1,000 next year in profits either.

I am also on disability and don't file taxes on that.

How would I file taxes this year? Next year would I need to start filing quarterly?

institutional site says $1.943 per share but retail side says we can’t say if it will be the same. Stupid but ok. Assuming it will be the same as institutional which it was last year and understanding I am going to pay 15% tax rate, is it better to reinvest and then sell shares for whatever I need or just elect to take as cash? If I reinvest and then sell shares which is typically the first in shares that I have held for a long time, am I being double taxed?

My boyfriend had roughly 33k in debt, I was able to file the OIC paperwork without any professional help (other than very nice redditors). After a year of prep and research, it took about an additional 8 months since sending all the paperwork to the IRS to get the official acceptance 🎉 luckily he does not have any assets and is low income. Here to advocate that if you are in a similar low income situation it is possible to file yourself and get approval!

I've read some differing points, so wanted to see if somebody could help me out here.

I've put a rental property in place (entirely passive i.e. Schedule E, used to be my primary home). I have a rental property manager handling tenants and have secured a 1-year lease for a tenant. The PM is paid 10% of monthly rent (will not exceed 2K this year, but will reach ~3K next year).

They collect their fee by withholding the 10% from the tenants month payments, which are then remitted to me. I am unsure if they are a C/S corporation, but can inquire.

Do I need to be issuing them a 1099-NEC for their property management fees? Sometimes I see people saying that 1099-NEC is primarily for active trade/business i.e. Schedule C and thus rental properties on a Schedule E do not need to issue one. Other times I see people saying it's better to issue one.

I have a rental property in another state and need to fly up there soon. I am wondering how to write off most of the trip, as some days will be personal. I can't sell the property due to a sagging rental market, though I have 30-35% equity in the home after repairs (conservatively).

I flew there last year to spend a month rebuilding after it got destroyed by tenants (feces on walls, ripped the carpets, smashed windows, etc.) I did take the full deduction last year for my travel, since I drove to the other state with all of my tools and a brand new set of appliances, water heaters, and repair parts.

The tenant this year is having some issues, and I think my property manager made a bad selection. I want to see the property, to walk it with the PM, and hire contractors as needed. I'm having issues seeing $500+ per month get siphoned for repairs when I spent $80k last year renovating. Repairs such as "fridge light bulb burned out" or "master bedroom AC not blowing hard enough."

My other two tenants living there have been situated for 5 years and 6 years respectively and reup every year without issue. We have raised the rent by roughly $125 in the past 5 years per unit.

I have a 7-day roundtrip flight, but I only expect the business side to take 3-4 days. I will be renting a truck from the airport to facilitate my needs of tools and repair items. I will likely be switching accountants this year because I am now fully running three separate businesses.

I sold intangible assets (email list, social media handles, etc) of my business. Someone mentioned I need to fill out form 8594, and I don't understand the form. I read through the information on the IRS website and I'm already stuck on the first part. Can someone please explain to me, in very easy terms, what the two "IF"s mean:

Both the seller and purchaser of a group of assets that makes up a trade or business must use Form 8594 to report such a sale if:

• goodwill or going concern value attaches, or could attach, to such assets and
• the purchaser's basis in the assets is determined only by the amount paid for the assets.

Hello,
I had my rental property painted this summer, but I was unable to obtain an invoice from the painter, who is an individual contractor. I also do not have his SSN or EIN information.
In this situation, am I required to issue a Form 1099? If so, how can I do that without having the necessary tax identification information?
Thank you.

Background is l’m a retired 30 year general contractor. Throughout my career I’d buy a fixer upper or two at rock bottom prices and fix and rent them out for no longer than 10 years. My thought process was I had full return on my money in 10 years rent, didn’t have much maintenance in the first 10 years, and rolled profit into another to avoid capital gains. Sold most of them during COVID and moved into the storage unit game. One of our last units is in my hometown and I’ve owned it for almost 15 years, duplex, and had an elderly family friend living there. My wife and I decided we’d hold on to this one as long as that tenant wanted to stay, and she has finally decided to leave at age 96. Time for a little more care for her. Anyway I have it sold to another investor and trying to decide what to do with the proceeds. Don’t think I want to expand much on our storage unit business as I’m almost 60, looking to slow down, and tired of people. Thinking about putting in a Delaware Statutory trust. Any advice, or anyone been involved in one? Not needing the capital at this time, looking to keep it invested for at least another 10 years.

I moved to NY from Canada this year and looking for a CPA for my taxes. I talked to one today and he is asking for $2,200 for the US taxes and $500 to $1000 CAD ($370 to $713 USD) for the Canadian taxes. Is this a good price or should I keep looking?

I received IRS Letter 6174 (not 6174-A to be specific) about crypto taxes. I am confident this is just a letter sent out to all people who have had an account with Kraken because the US government made Kraken share info with the IRS about people who have an account.

I made an honest effort in reporting my crytpo transactions. I didn't have too many so it wasn't that difficult, and I think I made an accurate reporting as short and long term capital gains. I may have been off by a few pennies, its difficult when your asset is something like 4895.92909938 and not 5000 shares. I am not too concerned with this part.

However, in the crypto sphere, which I am no expert in, sometimes there are random drops of "free" crypto currency. To make a comparison, if you own bitcoin you may get a few free XYZ tokens of some random crytpocurrency, which I have received. However I never sold those, and I never reported those. Their value was always less than $50.

I also just logged in and noticed a few random transactions that were made in my account related to these random free drops. They are exchanges back in forth with Ether. I honestly don't know what this is about since I didn't do the transactions myself. But they were all essentially $0, like $0.0000004673. I wasn't even aware of these so I also didn't report those.

In your expert opinion should I go back and make an amended return for these random transactions?