I'm a bookkeeper at a small firm and I just noticed something weird while entering payroll data. Our operations manager is having absolutely ZERO federal income tax withheld from his paychecks despite making around $75K annually. I was shocked when I saw this so I reached out to our payroll service provider about it. They sent me back a copy of his W-4 form and pointed to the "Exemption from withholding" section on the second page. From office gossip and things I've overheard, I'm pretty sure this guy hasn't filed his taxes in several years. I think he's using the loophole of "I didn't pay taxes last year" to claim he "had no federal income tax liability in 2024" on his W-4. And since he probably doesn't plan to file in 2025 either, he's using the same excuse looking ahead. I suspect he's doing this not only to avoid paying taxes but also to stay off the IRS's radar completely. While I'm annoyed that he's apparently getting away without paying what he legally owes, that's ultimately between him and the IRS. My real concern is about potential liability for our company. Could we get in trouble for this? Does the fact that we use a third-party payroll company offer any protection? Is "We just followed his instructions on the W-4" a valid defense if this ever comes up in an audit or investigation?

I can't seem to track down a W-2 from one of my employers for the 2023 tax year. The situation is frustrating because they went completely out of business sometime last year. All I have is their LLC name, the old business address (which is now empty), and their tax ID number. No phone contacts or email addresses for anyone who worked there. I tried calling the IRS for help, but when I follow all the automated prompts, I just get a recorded message telling me to "contact your employer" and if that doesn't work, to "call back after February for assistance." This recording seems outdated since it's already April, but I can't get past it to speak with anyone. Does anyone know another way to reach the IRS about this? I tried going through their online portal but don't see any option specifically for missing W-2 help - just transcript requests that need the information I'm trying to obtain in the first place. I looked at Form 4506-T which has an option for W-2 information, but it states that 2023 information (filed by employers in 2024) won't be available until 2025. I need this for my current tax filing! Any advice would be really appreciated. I'm stuck and running out of time before the deadline!

Hey everyone. I really appreciate you reading this. I'm a self-employed illustrator and I'm honestly terrible at managing the business side of things. I've been on my own most of my life so I don't have anyone to turn to for advice on this stuff. All my income comes through PayPal, which I know reports to the IRS. I have my 1099 for 2024 (plus the two years before that I still need to deal with). I desperately need to file my taxes by tomorrow to get my stimulus payment since the IRS doesn't have my payment information on file. The problem is I have absolutely zero receipts or expense records. I have a rough idea of what I might have spent on art supplies and business expenses, but I don't know exactly what qualifies as deductible. I tried using TurboTax but felt weird putting in dollar amounts I can't verify. Even being as honest as possible, the amount I owed was financially devastating. Though that's probably because I don't know what I'm doing. I called H&R Block hoping they'd help identify deductions, but they asked for the same info TurboTax wanted, so I don't feel like I'm getting actual help. Is there someone I can go to for real advice and support with this? Or am I stuck doing my best with TurboTax, guessing at my expenses, and dealing with a massive tax bill just so I can get the stimulus money in the short term? (I've started a Google Doc and physical folder to track all my expenses going forward, starting yesterday.) Thanks for any help. Sorry if this is too vague - happy to provide more info if needed.

So this is my first time as a US tax resident and I'm super anxious to get my taxes done ASAP. I moved here from Canada last March for a job opportunity (loving it so far!) and I want to be really on top of things with my filing. My company already sent me an email saying W-2s are going to be ready by the end of January, and I've been keeping all my receipts organized since I arrived. I'm pretty sure I'm going to get a refund based on my withholding, and honestly I could really use that money sooner rather than later (wedding planning is $$$ lol). What's the earliest date I can actually file my US taxes? I know the deadline is April 15th, but when does the IRS start accepting returns? I've heard different things from coworkers - one said January 15th, another said end of January, and someone else mentioned February. Does anyone know the actual earliest filing date for 2025?

I just got hired for a temporary position that's only going to last for the next two weeks. This is literally the only job I'll have this year, and I'm supposed to make around $1,900 total. I'm currently in college and my parents will be claiming me as a dependent on their taxes this year. I'm filling out my W-4 form and trying to figure out if I should claim zero allowances or what? I'm not really sure what the best approach is here since it's such a short-term thing. Does being claimed as a dependent by my parents affect how much gets withheld from my paycheck? What other things should I be thinking about with this situation? I've never had to deal with this before and want to make sure I don't mess anything up for next year's filing.