Has anyone dealt with Cash App's customer service for tax questions? I called them about a similar issue and the rep seemed completely confused about Roth recharacterizations. Wondering if I should just switch to a more traditional brokerage for my retirement accounts.

I went through almost the exact same situation last year with Cash App! The key thing to understand is that Cash App's interface isn't really designed for these complex retirement account corrections, so don't stress too much about finding the "perfect" reporting option within their system. Here's what worked for me: I downloaded all my account statements from Cash App that showed the original Roth contribution, the recharacterization to Traditional, and then the conversion back to Roth. These PDFs contain all the transaction details you need for tax reporting even if Cash App's built-in tools are lacking. For your 2024 taxes, you'll just need to file Form 8606 showing the $6500 non-deductible Traditional IRA contribution (which is what your recharacterized amount became). The actual conversion reporting happens next year when you get the 1099-R. One tip: when you do get that 1099-R next year, double-check that Cash App coded it correctly. Sometimes these newer platforms make mistakes with the distribution codes, especially for conversions that involved recharacterizations. Having your downloaded statements as backup documentation will be helpful if there are any discrepancies. You're handling this correctly - it's just that Cash App's user experience for these situations isn't great compared to traditional brokerages.

This is absolutely outrageous and I'm so sorry you're being put through this illegal exploitation. What your employer did is not just unfair - it's a clear violation of federal tax law called "worker misclassification" and they're hoping you don't know enough to fight back. You were 100% an employee based on everything you described - hourly pay, working at their location on their equipment, following their schedule, and them controlling how you performed your work. The IRS has very specific criteria for determining worker status, and you clearly meet all the requirements for employee classification. That December email asking to switch you "for easier accounting" is actually the best evidence you could possibly have - they literally documented their intent to violate tax law in writing! Save multiple copies of that email immediately. Here's exactly what I recommend: Send them ONE professional email explaining that retroactive reclassification is illegal under IRS regulations and creates an unfair $3,400 tax burden that should be their responsibility as your employer. Request they correct this by issuing a proper W-2 and paying their share of employer taxes. Give them one week to respond. If they refuse or ignore you, file Form SS-8 with the IRS to get an official worker classification determination, and file Form 8919 with your tax return to report the uncollected employer taxes they should have paid. Don't feel guilty about "causing trouble" - THEY caused trouble when they decided to break federal law to steal money from a college student. You have an ironclad case here with that December email as smoking gun evidence. Fight this and make them pay what they legally owe instead of letting them dump their tax obligations on you!

This is absolutely infuriating and unfortunately way too common in today's workplace. What your employer did is completely illegal - they cannot retroactively reclassify you from W2 to 1099 after you've already worked as an employee for months. This is textbook worker misclassification designed to shift their tax burden onto you. Based on everything you described - hourly pay, working at their location, following their schedule, using their equipment, them controlling how you did your work - you were clearly an employee under IRS guidelines. The 20-factor test the IRS uses would definitely classify you as an employee, not an independent contractor. That December email where they asked to switch you "for easier accounting" is actually smoking gun evidence of their illegal intent. Screenshot that email immediately and save it in multiple places - it's going to be crucial for your case. Here's what I'd recommend: First, send them ONE professional but firm email explaining that retroactive reclassification violates federal tax law and creates an unfair $3,400 tax burden that should legally be their responsibility. Give them exactly one week to respond with a plan to correct this by issuing a proper W-2 and paying their share of employer taxes. If they refuse or ignore you, file Form SS-8 with the IRS to get an official worker classification determination. You can also file Form 8919 with your tax return to report the uncollected Social Security and Medicare taxes they should have paid. Don't feel guilty about "causing trouble" - THEY caused the trouble when they decided to break federal law to save money at your expense. You have an ironclad case here with that December email as evidence. Fight this and make them pay what they legally owe instead of letting them dump their tax obligations on a college student!

This is such a helpful thread - I'm learning so much about divorce property transfers! I have a quick follow-up question about the timing requirements. If your father decides to move back into the house to start establishing it as his primary residence for the Section 121 exclusion, does the IRS have any specific requirements about how "primary" it needs to be? For instance, if he's semi-retired and travels frequently, or if he spends weekends helping care for elderly parents, would that impact his ability to claim it as his primary residence? I'm asking because my situation is similar - I bought out my ex's share of our home but I travel for work about 40% of the time. I want to make sure I'm not jeopardizing the primary residence status by being away frequently, even though all my mail goes there and it's definitely my main home base. Also, does anyone know if there are any safe harbor rules or guidelines about what percentage of time you need to actually be physically present at the residence? I haven't been able to find clear guidance on this specific aspect.

This thread has been incredibly informative! I'm going through a similar situation and wanted to add one more consideration that might be relevant for your father's case. Since the property wasn't specifically addressed in the divorce settlement agreement, it's worth making sure the buyout transaction is properly documented as being "incident to the divorce" for Section 1041 purposes. Even though the divorce is finalized, having a written agreement (even a simple one) that references the divorce and states that this buyout resolves the property division could strengthen the position that this transfer qualifies for non-recognition treatment. I'd also suggest your father consider getting a property appraisal around the time of the buyout if he hasn't already. While it won't change the basis calculation under Section 1041, having documentation of the property's fair market value at the time of transfer could be helpful if the IRS ever questions whether the $95k payment was reasonable or if there were any gift tax implications. One more practical tip - if your father does decide to move back in to start the primary residence clock, he should update his address with the IRS immediately by filing Form 8822. This creates an official record with the timing that supports his claim of making it his primary residence for Section 121 purposes down the road. The documentation advice from others here is spot on - keeping detailed records now will save headaches later!

For anyone else with the same question: I just wanted to add that the reason the Supplemental Information Form exists is because of a timing issue. Brokerages have to submit 1099-Bs to the IRS by a certain deadline, but sometimes they don't have all the final adjusted cost basis info ready by that date (especially for complicated situations like wash sales that happened late in the year). Rather than delay sending you any form at all, they send the official 1099-B that went to the IRS, plus the Supplemental form with the updated, more accurate info for your personal tax filing. It's annoying but actually helps you get your forms earlier while still having the most accurate numbers.

This thread has been incredibly helpful! I'm in a similar situation but with an added twist - my brokerage sent me THREE different forms: the original 1099-B, a Supplemental Information Form, AND a "Corrected 1099-B" that came a week later. The numbers are all slightly different between the three forms. I'm assuming I should use whichever form is most recent (the Corrected 1099-B), but now I'm second-guessing myself since everyone here is talking about using the Supplemental form instead of the original 1099-B. Has anyone dealt with getting both a supplemental form AND a corrected 1099-B? Which one takes priority when they have different numbers? My tax software is asking me to enter just one set of numbers, and I don't want to mess this up since we're talking about a pretty significant dollar amount difference between the forms.

Also remember that with 1099-NEC income you might need to make quarterly estimated tax payments next year to avoid penalties! I learned this the hard way last year when I got hit with an underpayment penalty.

This is such great advice in this thread! I'm actually dealing with a very similar situation - W-2 from my main job and just got my first 1099-NEC from some consulting work I did last year. One thing I wanted to add that I learned from my accountant friend is to keep really detailed records of ALL your business expenses throughout the year, not just at tax time. I started using a simple spreadsheet to track every business-related purchase, mileage, and even the percentage of my phone/internet that I use for work. Also, if your 1099-NEC income is going to be ongoing, definitely look into opening a separate business checking account. It makes tracking expenses so much easier and helps if you ever get audited. Some banks even offer free business accounts for sole proprietors. Thanks everyone for sharing your experiences with the different tools and services - definitely bookmarking this thread for next year!