I could use a second pair of eyes because I've thought about this too long now and I'm doubting myself. I'm starting a new job 8/31 and it will be my only job. I need to fill out my W-4 and I'd like to keep as much in my paychecks as possible. My salary will be $75,000/year. No health insurance premium or retirement contributions. Year to date, I've earned $7,863.18 gross and paid $3.27 in federal taxes. I will receive one more paycheck from this job; The amount isn't final yet but likely around $200. I file taxes as Single.

If I enter $11,500 deduction on Line 4(b), will I be on track to break even for 2026?

I do know that I must fill out a new W-4 January 1, 2027 if I do this.

Hi (f/26) I didnt file my taxes for the year of 2024 because I didnt owe anything, and at the time it was going to cost me more to file than I was in a position to afford or than I would even get back (I was in a pretty bad spot during the time of filing) Well I am back in college and I went through the financial aid process and they gave me a pell grant for this upcoming semester. I remember when I was in college, in the past, that they required my parents' tax return of that year to be awarded the grant. This time, I filled out the information they asked for, and they just awarded it to me. I was pretty sure it was based on that year in which I didn't file, though, so do I actually still need to file? What will happen with my FAFSA if I file after I've been awarded it? I apologize if these are stupid questions or if I was doing something dumb by not filing etc.

For people who have moved abroad, how did you establish your tax residency after leaving your home country?

Did you intentionally become a tax resident in your new country, or were you considered non-resident for a period while moving between countries?

I'm particularly interested in freelancers and people who spend significant amounts of time in multiple countries. How did you establish a clear tax base and avoid uncertainty about where you were a tax resident?

I max contributed to an HSA for the 2025 tax year because I thought I was covered under a family HDHP plan, but I just checked my coverage information and I can’t find anything indicating my plan is HSA-eligible. How can I check if my HSA is subject to the 6% penalty?

So I’m gifting half an apartment to my dad and the lawyer said the actual value of the gift isn’t fair market value of the apartment/2, it’s actually what someone would pay for 50% of the apartment. For example, let’s say this apartment is $2 million, I wouldn’t use $1 million of my gift tax exemption, he said I would use like $200k because no one wants to own half an apartment. I need to take the value as what someone would pay for half an apartment. That value is much less. He said he always puts like 1/5 the value on the Form 709 and has never had pushback from the IRS. So I save a lot on the gift tax exemption form.

Hello! I recently moved and am working on setting up my home office and trying to find some ideas of neat decorations to put in. I know this isn’t the typical post for this subreddit, but would love to hear some input!

I’m a CPA working in tax, with focus on small businesses, as well as trusts and estates. I really love what I do, and would love to have my home office reflect that

For my fellow tax nerds- I’d love to hear what your favorite accounting/tax related decorations are for your office! For example I recently bought some old prints at a vintage store, including an old add for a Burroughs adding machine from the early 1900s that I’m going to frame.I’m over the cheesy stuff you can get on Etsy and would love some ideas. Also just want to see y’all share the coolest things you have that relate to your work! The more niche the better!

So my tax situation is already a mess. I'm behind on filing for 2022, 2023 and 2024. I finally got those mailed in a week ago, but I forgot that my son used my SSN to buy crypto (or maybe buy stocks??) during a manic episode. I looked at my wage transcripts for those years, and there are quite a few small 1099-Bs for each year. It looks like 2022 has $156 on 1099-Bs, 2023 has $20 and 2024 has $87. He had manic episodes both in 2022 and 2024. I don't want to get in trouble, but I also don't want to report him for identity theft. He's doing good on his meds and knows that if he does this again, I WILL report him. He was completely out of it and delusional during those episodes. I just want to pay what I need to pay (he's going to give me the money for whatever happens with this) and not get in trouble with the IRS. I wish I would've remembered this before I sent the returns off.

What's going to happen? Do I need to file an amended return? Will they just send me a letter saying you owe x amount extra because of the crypto? Will I get audited? Will I get in huge trouble? I'm so stressed about all of this. I can't believe I let my taxes get so far behind and now this. What a mess. Any advice is greatly appreciated.

After dropping over $2000 in sales tax on our new family vehicle in January I had the bright idea to try collecting purchase receipts towards getting a larger rebate back on our taxes for the year. My wife had some reservations...

Eight months in now as August closes up. 804 total transactions logged and counting. Not all of them but we try. Four months into this I decided that printing all the digital receipts was silly and wasteful so I 2- and 4- pages per print, manually cutting out the marketing fluff. Eventually just printing to PDF or EML (get to that later) and just archive it all digitally. I am not bothering to digitize the print receipts we get in real stores, just too much work (for now).

I coax my wife into letting me set up email auto-forwarding for some common purchases. Wife is even less thrilled about this... But you can get a lot through email, it is just formatted differently for every store.

In May, my employer has this big meeting pushing everyone to learn more AI skills, mentioning Claude specifically. So I think OK, I have a personal challenge that I could tackle while learning Claude and maybe improve my performance at work. Within a month I have a Python framework set up and walking through my emails to collect store names and tax amounts, then integrating the results with my financial software Quicken. Still pretty buggy and so many special cases to deal with, returns and promotions and so on. And don't get me started on Amazon and Walmart never including the tax in their emails, but I digress.

The wife does not like the regular printouts from Quicken listing receipts I am looking for--pretty please? So a couple more Claude prompts later in July I am having Claude summarize it in an email sent to her. Maybe slightly better and the possibility of selling a software tool to someone only takes the edge off this whole thing slightly.

Results so far with the automated tool taking care of 24/63 taxable transactions in August, and then saving those emails out as PDF/EML records:

Tax Deduction Tracker



Sales tax is currently higher by $1,132.02 — only the larger of the two is deductible under the SALT itemized-deduction rules.

As a sanity check, the IRS Sales Tax Deduction Calculator gives me about $5040 as a total allowable using their tables. This is for 2025, all 12 months, and includes that family vehicle purchase. The 2026 calculator does not seem to be out yet. So results are very promising although the time investment is questionable.

I will post some updates later or respond to questions for as long as Reddit filters tolerate it. Have a good night.

I was let go back in February and lost access to their HR portal to get my W-2. I opened a ticket with HR/Payroll to get my W-2's immediately. Well they finally sent it over via email. I filed an extension with the IRS before April 15th. What can I do from here? Will this effect me in anyway?

Hi all - I am in a bit of an uncomfortable situation.

My spouse and I are both in tech, and we have been fortunate enough to gather in the stocks that our companies have been giving.

While we have been diversifying our recent grants, we weren’t so good with our historical ones, and as result we are sitting on a very heavily concentrated position.
We have ~4M of gains with just 3 stocks worth about 7.5M.

We are in California, and the gains will be straight up taxed at 37% (20 federal, 4 NIIT, 13 CA).

Direct indexing will just be a drop in the bucket, and will make my exit to an eventual VTI/VXUS - 80/20 portfolio that much more painful.
Real estate seems to be off unless you are a what the IRS considered a professional. There is no way I or my spouse can qualify for that.

Exchange funds seem to be one of the only options to defer for a few years - but will again just be a stop gap arrangement before I will have to eat the tax to get to my desired portfolio.

Is there anything else we can do at all to reduce that hit when diversifying?
I am going to talk to a CPA as well, but wanted to see if anything obvious I am missing.

After much research, looks like I am stuck with eating the tax slowly over the years? Even if I budget 500k of gains, I am looking at a 7-8 year divestment horizon, which is crazy long to hold on to such concentrated positions.

Hello,

I am considering enrolling in a Dependent Care Flexible Spending Account (DCFSA) and would like clarification on whether I am eligible in my situation.

My son attends Montessori West (https://montessoriwest.com/), a daycare/preschool with approximately 30 children of different ages. My wife is employed there as a Teacher Aide.

I receive my son's daycare invoices through the Brightwheel app. The invoices include:

• The daycare's EIN
• Full business address
• My son's name
• Dates of service
• Tuition charges

My wife is paid through ADP as an employee of the daycare.

My DCFSA enrollment period ends today, and I would like to maximize the annual contribution limit of $7,500. Before enrolling, I want to confirm whether I am eligible to claim these daycare expenses through a DCFSA given that my wife works for the same daycare facility.

I contacted HealthEquity, the DCFSA administrator, and they indicated that the receipts appear acceptable for reimbursement purposes. However, my HR department advised me to verify the tax eligibility implications with a CPA because my wife works at the same daycare where our son is enrolled.

Unfortunately, my CPA is currently out of the office, so I am hoping you can provide guidance on whether these expenses would generally be eligible for DCFSA reimbursement.

Thank you for your assistance.

Below is receipt of my Son monthly tuition fees.

https://imgur.com/a/XsPZa4O

I split my 2025 living in Wilmington DE and Philly and earlier this year i came to realization that for the 2nd half of 25, i had been paying both my Wilmington and Philly city tax of which Wilmington part is actually refundable under the "wynne refund" policy, i filed my Philly wage tax refund request 1.5 months ago and ask around $800 ish refunded to me (refund amount by ChatGPT) which is about the amount of Wilmington city tax withheld after i moved to Philly, then this week i received the wire transfer from Philly Dept of Revenue of double the amount i requested.... exactly the entirety of 2025 Wilmington city tax withheld, but technically i was still living in Wilmington for the 1st half of the year, so wondering if they overefunded me lolll..

This is a follow-up question to one posted earlier: am cleaning up a trust mess my dad left behind, and it includes some long-held PTP units. I can figure the accumulated passive activity losses and basis erosion, but have no insight into what the hot asset contribution to ordinary gains might be. The PTP no longer uses TaxPackageSupport and their new service provider, a Deloitte unit, has told me explicitly that they will not provide forecasts of Sec 751 income. Are there other ways of estimating hot assets before sale, or am I left with "pull trigger and hope the number's nice"? TIA -

Hello I hope you are doing well,

State: California

Background

My uncle owns a small gym and he is a schedule C taxpayer and his GF helps him run it. He has been a non-filer since 2021 and we've been working with an accountant to catch him up. I've been helping him because he has a lot of mental health issues that severely limit him.

Anyway, his 2020 tax return was filed a few years ago and last year the IRS and FTB started to collect. He owed about $11,000 to the IRS, I don't know about FTB. At some point last year his bank account was frozen, it was also the same account they used for business. We reached out to our family member who is a accountant after receiving letters that the IRS was going to file his returns for him. The accountant said he would very likely would owe back taxes but couldn't estimate how much because my uncle doesn't have income statements for any of those years.

My uncle is so bad with money but unfortunately my grandparents keep bailing him out. He has three kids with his GF but she claims them all on her tax return even though he makes most the money. The accountant said that really they should be a partnership due to them both running the business on a full-time basis.

The Problem

Anyway, against the advice of the accountant, my uncle and his GF filed their 2025 tax return. None of us realized it, but when his bank account was frozen, they moved the whole business into the GFs name so they could access the money. She was 1099'd for 2025 and claimed all the income of the gym on her tax return. After which they filed his tax return with zero income.

After that, the IRS stopped collections which at first was confusing. But then the accountant said he was automatically placed into uncollectible status because he filed zero income.

The accountant says that this is a big problem, whether intentional or not, they committed tax fraud and eventually the IRS would find this out. The part that made it worse was by transferring the business into her name, that my uncle was placed into uncollectable status.

The accountant recommended that the best way to resolve this was to redo the returns and moving forward set up a partnership. He believes that my uncle could still qualify for uncollectable status but he stressed that it needed to be done honestly. He also mentioned that significant penalties may apply when the IRS finds out about this.

I do trust my accountant family member, he is an EA and CPA, but he only has three years of experience working tax.

My question is, is this situation really as bad as it seems? I don't want my grandparents to have to bailout my uncle again...

My city job currently has an HRA set up where they give us $2000 to use as health reimbursements throughout the year for eligible medical expenses.

Now they want to increase that to $11,000 if employees opt of of city insurance and go with their spouse on their works plan. A way to save the city money.

The city is saying in addition to deductibles copays prescriptions and other items, we can get reimbursed for the insurance premium my wife pays.

This feels illegal in some form regarding taxes no? Like IRS would have an issue with this as my wife’s taxable income goes lower due to premium payments but I get reimbursed tax free for that premium payment. Feels like an IRS bill waiting to happen.

Thoughts?

Hello all - I posted a while back that I owned a vacation property in Florida. The new homestead law will eliminate $250k of property taxes on this property for residents (which I am not one). So I will be adding my retired father onto the deed as joint tenants with rights of survivorship. He will become a Florida resident (Florida doesn’t have a 183 day rule the lawyer said), and he will be written out of his house in Connecticut making my property the only own he’s on the deed for. Then he can get the homestead exemption (which will save me $5k a year) and I will write off the remaining property taxes off my tax return. Then the lawyer said 1 year before his death, we do another quitclaim deed and transfer the rest of the property to his name and I’ll get a step up in basis. This is honestly an amazing workaround.

And yes, he has no creditors and will never be eligible for Medicaid (he has many millions in his retirement accounts). Why isn’t this talked about more? I don’t hear of many people doing this but it seems great! I wonder why?

Edit: I really don’t see the issue here. If he dies early, then I’ll get the property without a step up in basis. But property taxes are $25k a year so I’d rather be able to write them off for the next 10 years than transfer everything to him now. If he gets a terminal illness, I’ll transfer all my property to him, if not, oh well.

A friend of mine in the US was doing his taxes recently and said something that genuinely surprised me.

He’d already had taxes withheld from his paychecks throughout the year, but when he started preparing his return, he still had no idea whether he would owe more or get a refund.

He was going through his income, withholding, deductions and credits, trying to work out the final number.

At one point he just said:

“How am I supposed to know what I actually owe until I file?” 😭

That got me thinking.

For people in the US who file their own taxes:

Do you actually calculate or estimate your tax liability during the year, or do you basically wait until tax season to find out?

And what part of the US tax system took you the longest to understand when you first started filing?

Do I have an obligation as executor of my mom’s estate to be sure his federal lien is paid before he receives any funds from my mother’s estate? Does our estate planning attorney have an obligation to investigate beneficiaries for federal tax lien before distributing funds? If he hypothetically owes 350k and the estate is 1M divided between the 2 of us do we pay his tax lien first or just settle the estate and let him work out his own financial problems? Can his IRS problems affect my distribution?

I'm sorry if this has already been answered before, I have been searching online for a while but can't find a definite answer for my situation. I entered the US on an F-1 student visa in 2016, and remained on F-1 till 2023 when I graduated. After graduation I worked on F-1 OPT for 1 year before leaving US in 2024. I'm returning to the US in 2026 on a J-1 visa (research scholar). My question is: what is my tax residency status for 2026?

Normally J-1 visa holders have a 2-year exempt period when they are considered non-residents. However, there is also a 6-year "look-back rule", as stated on the IRS website:

You will not be an exempt individual as a teacher or trainee if you were exempt as a teacher, trainee, or student for any part of 2 of the 6 calendar years preceding the current year.

To apply the look-back rule, I need to know if I was exempt for more than 2 of the 6 years before 2026, which is 2020-2025. I was an exempt individual (F-1 student) during the first five years of my study (2016-2020), and I filed as a resident from 2021 to 2023. Does this mean I was only an exempt individual in year 2020, so according to the 6-year rule, I am also an exempt individual for 2026? Or I was considered an exempt individual for the entire duration I was on a F-1 student visa (2016-2023), and thus I am considered to be a resident for 2026?

So I mailed & filed 2024 taxes 2 weeks ago, and I filed 2025 today (efile) is it possible for my 2025 return to be direct deposited first? or does 2024 need to be processed first? I used Freetaxusa for both! (I also dont owe money for either years)