6 Quick question - has anyone actually dealt with the IRS directly on this kind of issue? I'm in a similar situation (employer didn't withhold for 1 year claiming I was exempt), and I'm wondering if I should just bypass my former employer entirely and go straight to the IRS?

This is a frustrating situation that unfortunately many employees face. Your employer made a significant error, and you're absolutely right to question their attempt to make you responsible for their penalties. Here's what you need to know: You are only legally responsible for YOUR portion of FICA taxes (7.65% of your wages for those 3 years). You are NOT responsible for: - The employer's matching portion (another 7.65%) - Any penalties or interest charges - Their processing fees The employer is required by law to withhold and remit FICA taxes, and when they fail to do so, they're responsible for all penalties and interest that result from their error. My recommendation is to document everything in writing with your former employer. Give them a reasonable deadline (like 30 days) to provide you with a corrected statement showing only your portion of the taxes owed. If they refuse, you can file Form 8919 with your next tax return to pay your portion directly to the IRS, and let the IRS handle collecting the employer's portion and penalties. Don't let them intimidate you into paying for their mistake. The law is clear on this issue.

I completely understand your frustration with Schedule C categorization! I went through the exact same struggle in my first few years of business filing. For your cash back rewards, since you're only getting $4-5 monthly, I'd definitely recommend the "Other Income" approach that others have mentioned. The IRS isn't going to scrutinize such small amounts, and trying to allocate them across multiple expense categories would be more trouble than it's worth. Just be consistent year to year with whatever method you choose. Regarding your insurance questions, you're on the right track. Workers compensation insurance absolutely goes on Line 15 "Insurance (other than health)" - that's a legitimate business expense. However, for your disability insurance, it depends on the specifics. If it's personal disability insurance covering you as the business owner, it's generally not deductible as a business expense. But if it's disability insurance you're providing to employees, then it would also go on Line 15. One tip that helped me a lot: keep detailed notes about why you categorized things the way you did. If you ever get questioned later, having your reasoning documented makes everything much smoother. Don't stress too much about getting every tiny detail perfect - consistency and reasonableness are more important than perfection, especially for smaller amounts like your cash back rewards.

Hey there! I totally feel your pain on the Schedule C classification struggles - I'm dealing with similar issues in my second year of business too. For the cash back rewards, I've been going back and forth on this myself. Since your amounts are so small ($4-5 monthly), I think the "Other Income" approach that others mentioned makes the most sense. I was trying to be super precise and allocate mine proportionally, but honestly for such tiny amounts it's probably not worth the headache. On the insurance front, I had the exact same confusion! Workers comp definitely goes on Line 15 - that one's straightforward. For your disability insurance though, if it's covering you personally as the business owner (which it sounds like it is), it's typically not deductible as a business expense. I made that mistake on my draft return and had to correct it. One thing that's been helping me is creating a simple spreadsheet where I track my reasoning for each categorization decision. That way if I ever get questions later, I have documentation of my thought process. It's also been useful for staying consistent year to year. Hope this helps and good luck with your filing!

Been having the same issue since around 6:30 AM! Really frustrating because I was hoping to see if there were any updates on my refund status today. The timing is especially annoying since it's Monday morning and I wanted to check before work. I tried both desktop and mobile - desktop just loads forever and mobile gives that same "Transcripts are unavailable" error you're seeing. Cleared my browser cache, tried incognito mode, even switched to a different wifi network thinking it might be a connection issue on my end. It's definitely a system-wide problem and not just you. I've seen this happen a few times during filing season - usually resolves by afternoon but sometimes takes longer. The IRS really needs to invest in better infrastructure because these outages happen way too frequently when people need to access their info most. Hopefully it's back up soon! I'll probably try again around lunch time and see if it's working by then.

I'm experiencing the exact same issue! Been trying to access my transcript since about 6:45 AM and getting that same "Transcripts are unavailable" error. This is my first time dealing with an IRS system outage and I was starting to panic thinking something was wrong with my return filing. Really appreciate everyone confirming this is system-wide - makes me feel much better knowing it's not an issue with my account specifically. I'm also checking daily for refund updates and this outage couldn't have come at a worse time since I'm expecting movement on my return status. Has anyone noticed if there's a pattern to when these outages typically get resolved? I'm wondering if I should just wait until this evening to try again or if it's worth checking periodically throughout the day. Thanks for posting about this - it's reassuring to know I'm not alone in dealing with this frustration!

19 Has anyone actually had success getting an organization to reissue a corrected tax form? My university issued me a 1099-NEC for a research stipend that should have been on a 1098-T, but their accounting department keeps saying "that's just how we report it" and refuses to fix it. I'm going to end up paying hundreds extra in self-employment tax!

I went through something very similar with a nonprofit I worked with last year. They issued me a 1099-NEC for what was clearly described as an "educational development stipend" in my original contract, but their accounting department treated it like regular contractor income. The key thing that helped me was getting a written statement from the program director confirming that the stipend portion was specifically for my professional development and continuing education costs, not compensation for services rendered. I also had to show that the stipend amount was reasonable relative to actual educational expenses I incurred. With that documentation, I was able to report the stipend portion as "other income" on Line 8i of Schedule 1 (Form 1040) rather than as self-employment income. I attached a statement explaining the nature of the payment and referencing the organization's written confirmation. The IRS didn't question it during processing, and I saved about $400 in self-employment taxes. The regular contractor work portion still went on Schedule C as usual. Just make sure you have solid documentation about the educational purpose and that it wasn't contingent on work performance.

Wondering if anyone knows how this would affect future W-2 employment? If the friend doesn't file for the sole proprietorship but then starts filing normally with their new W-2 job next year, will that trigger the IRS to look backward?

Your "friend" really needs to file that return, even if it's messy. I work in tax prep and see this situation all the time - the fear of filing an imperfect return often makes people avoid it entirely, which always makes things worse. Here's what I tell clients in similar situations: the IRS would rather see an honest attempt at filing with some organizational issues than no filing at all. They have programs specifically for first-time business owners who made mistakes. A few practical steps your friend can take right now: 1. Gather ALL bank statements for the business account (or personal account if mixed) 2. Make a simple spreadsheet listing income and expenses by month 3. Don't worry about perfect categorization - basic business expenses vs personal is enough to start 4. File for an extension if needed to buy more time to organize The penalties for not filing are harsh, but there are often penalty abatement options for first-time filers who can show reasonable cause. The key is showing good faith effort to comply, which means filing something rather than nothing. Also, closing the business license doesn't erase the tax obligation for the year it operated. The IRS will still expect to see that Schedule C on the 2022 return.