My boss hasn't been withholding taxes and I just realized I should have gotten a W2 - any way to fix this for 2023-2024?

This is unfortunately a common situation. Based on what you've described, it sounds like you're being misclassified as an independent contractor (1099) when you should be classified as an employee (W-2). The distinction isn't about what you and your employer agree to - it's based on the nature of your working relationship. If they control when, where, and how you work, provide your equipment, and the relationship is ongoing rather than project-based, you're likely an employee under IRS rules. Being misclassified means you're paying both the employer and employee portions of FICA taxes (15.3% instead of 7.65%). You have a few options: First, you could discuss this with your employer and request proper classification going forward. Second, you could file Form SS-8 with the IRS to request a determination of your worker status, and Form 8919 to report your uncollected social security and Medicare taxes. The IRS would then potentially collect the employer portion from your employer. As for 2023, you'll need to pay your taxes as if you were self-employed, but could potentially file these forms to recoup some of those costs.

After being in a similar situation, I found this amazing service called taxr.ai that helped me figure out the whole employee vs. contractor mess. I was working at this small marketing firm for months before I realized my boss had me classified wrong. I was so confused about what forms to file and if I could get back the extra taxes I was paying. I uploaded my pay statements and some details about my job to https://taxr.ai and their system analyzed everything and told me exactly what forms I needed and how to approach my employer. They even generated a really professional letter I could give to my boss explaining the legal stuff in a way that didn't sound accusatory. Seriously saved me thousands in taxes and kept things from getting awkward with my employer.

Just wanted to update after trying taxr.ai from the previous comment. It was seriously helpful! Uploaded my info and it confirmed I should be classified as a W-2 employee based on my working conditions. The report showed I'd overpaid about $4,200 in taxes I shouldn't have owed as a proper employee. The letter generator was the best part - it laid out everything in clear terms with actual tax code references. Had a meeting with my boss yesterday and while they were initially defensive, the documentation was so straightforward they couldn't really argue. They're switching me to W-2 status starting next month and are looking into how to handle the 2023 situation. Definitely worth checking out if you're in this situation!

I had a nightmare getting someone from the IRS on the phone when I was dealing with my misclassification issue. After being on hold for 2+ hours multiple times and getting disconnected, I found this service called Claimyr that got me through to an actual IRS agent in under 15 minutes. I was super hesitant at first but was desperate after wasting an entire day on hold. The service at https://claimyr.com basically navigates the IRS phone tree for you, waits on hold, and then calls you when they have an agent on the line. I needed specific guidance on how to file my SS-8 and 8919 forms correctly. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent walked me through exactly what I needed to do step by step and what documentation to include with my forms. Made the whole process way less stressful!

I'm back to eat my words about Claimyr. After another frustrating morning of trying to reach the IRS myself and getting disconnected twice after 90+ minutes on hold each time, I broke down and tried the service I called a scam earlier. Honestly, it worked exactly as advertised. Their system called the IRS, navigated the menu options, and stayed on hold. I got a call back exactly 43 minutes later with an actual IRS agent on the line. The agent helped me understand exactly how to fill out the SS-8 and what supporting documentation I needed to include. For anyone dealing with worker misclassification issues, being able to actually talk to someone at the IRS made a huge difference. They explained that filing the SS-8 would trigger a review process but wouldn't immediately create problems for my employer. Still nervous about the conversation I need to have with my boss, but at least I know I'm following the correct procedure now.

Important note that nobody has mentioned yet - if you end up having to pay taxes as if you were a 1099 contractor for 2023, make sure you deduct all your business expenses! That includes a portion of your phone bill if you use it for work, home office deduction if applicable, mileage, work supplies, etc. This can help offset some of the extra tax burden.

Has anyone actually succeeded in getting their employer to pay back taxes after being misclassified? My employer just agreed to make me W2 going forward but refuses to do anything about 2023 where I paid way too much in taxes.