Just wanted to add from my experience - when I did a similar Roth conversion, I found that increasing my withholding was much easier than dealing with estimated payments and Form 2210. The key thing to remember is that you need to calculate how much extra to withhold based on your marginal tax rate for both federal and state. For a $110k conversion, you're probably looking at withholding an extra $24k-$30k depending on your bracket. I divided that by my remaining paychecks and adjusted my W-4 accordingly. Make sure to account for both federal and state taxes when calculating the amount. One tip: if you're close to year-end and don't have enough paychecks left to spread out the withholding, you might want to do a combination approach like Christopher mentioned - make a partial estimated payment now and increase withholding for what you can cover through payroll.

Great discussion here! I went through a similar situation with a $85k Roth conversion last year. One thing I'd add is to double-check your state's specific rules if you decide to go the withholding route. While the federal withholding approach works beautifully (treated as paid evenly throughout the year), some states like California have different rules for estimated payments that don't follow this federal treatment. Also, if you're considering the withholding strategy, make sure to calculate the exact amount needed including any potential Net Investment Income Tax (3.8% Medicare surtax) if your modified AGI exceeds the thresholds. For a $110k conversion, this could add another $4,180 in taxes if you're over the limit. One practical tip: I used the IRS withholding calculator on their website to double-check my math before submitting the new W-4. It helped me verify that my increased withholding would cover both my regular tax liability plus the conversion taxes without overpaying significantly.

My tax guy told me not to stress about tiny amounts like this. He said the IRS is focused on people hiding thousands, not a few hundred bucks. Just something to consider.

I had a similar situation with Cashapp income last year! The key thing to understand is that you're legally required to report ALL income, even if it's under $600 and you didn't get a 1099-K form. The $600 threshold just determines whether Cashapp has to send you tax documents - it doesn't change your obligation to report what you earned. For your $480 in side gig income, you'll need to report it as self-employment income on Schedule C. The good news is that you can also deduct legitimate business expenses (gas, supplies, etc.) which might reduce your tax liability. Even if you don't have perfect receipts, bank statements can serve as documentation. While the IRS may not catch small unreported amounts, it's not worth the risk of penalties and interest if you're ever audited. Better to be compliant from the start, especially since you're establishing a pattern of side income that might grow in the future.

Wait i'm confuses...i thought business losses were reported on a schedule C and capital losseson a schedule D? Are they not treated the same on the 1040?

Just wanted to add a practical tip for tracking all this - keep meticulous records of your business activities and time spent if you're claiming active participation. The IRS loves to challenge material participation claims, especially when substantial losses are involved. I learned this lesson when I had a side consulting business that lost money its first year. Even though it was clearly active business income (I was doing all the work myself), I didn't keep great time records. When my return got selected for review, I had to scramble to reconstruct my activity logs from emails, calendar entries, and receipts. Also worth noting - if you're planning to convert your LLC to an S-corp next year, make sure you understand how that affects loss carryforwards. Generally, losses from your sole proprietorship can't be used by the S-corp since they're different tax entities. You'd want to utilize as much of the current year loss as possible before making any entity changes. The interaction between different types of income and losses is definitely one of the more complex areas of tax law, but understanding it can save you thousands!

One thing that hasn't been mentioned yet is the importance of keeping detailed records of your Robinhood cash sweep deposits. As an NRA, you'll want to maintain documentation showing that the interest truly comes from bank deposits rather than other investment activities. I'd recommend downloading your monthly statements from Robinhood that show the cash sweep transactions and which partner banks your funds were deposited into. This documentation will be helpful if the IRS ever questions the exempt status of your interest income. Also, be aware that if you have other types of interest income from Robinhood (like from bonds or other securities), those would be treated differently and might not qualify for the bank deposit exception. The 1099-INT should break down the different types of interest, so make sure you're only applying the exemption to the actual bank deposit interest from the cash sweep program.

As a fellow NRA dealing with similar tax questions, I want to emphasize something that helped me understand this better: the key distinction is between "portfolio interest" and "bank deposit interest" - both can be exempt for NRAs, but under different rules. For Robinhood's cash sweep program, you're almost certainly dealing with bank deposit interest since they explicitly state they sweep uninvested cash into FDIC-insured deposit accounts at partner banks. This falls squarely under the bank deposit interest exemption in IRC Section 871(i)(2)(A). However, I'd strongly recommend verifying this by looking at the specific language on your 1099-INT form. Box 1 should show the interest amount, and there might be additional codes or descriptions that clarify the source. If it says something like "cash sweep interest" or references partner banks, you're good to go with the exemption. One last tip: even though it's exempt from federal tax, don't forget to check if your state has any reporting requirements if you have any U.S. state tax obligations. Most states follow federal treatment for NRAs, but it's worth confirming.

I gave up on FreeTaxUSA for this very reason and switched to TaxAct. Their interface makes finding Form 8936 for the Clean Vehicle Credit much easier. It's directly listed in their credits section without having to hunt through multiple layers of menus. The Schedule A part confused me too, but it turns out it's only needed if you leased the vehicle. If you purchased outright, you just need to complete the regular Form 8936. Just wanted to provide an alternative in case anyone is still struggling. Sometimes switching tax software is easier than fighting with a confusing interface, especially when thousands of dollars of tax credits are at stake.

I had this exact same problem with my Nissan LEAF purchase! After reading through all these helpful responses, I wanted to share what finally worked for me in FreeTaxUSA. The key is the sequence - you absolutely MUST complete these sections in order before the Clean Vehicle Credit option becomes visible: 1. Complete ALL income sections (W-2s, 1099s, etc.) 2. Go through the entire "Deductions" section 3. Complete the standard credits (Child Tax Credit, etc.) 4. ONLY THEN will "Other Credits" or "Miscellaneous Credits" appear Once you get to that section, look for "Clean Vehicle Credit" or search specifically for "Form 8936". The software will then walk you through the questions about your vehicle purchase. For the Schedule A confusion - that's ONLY for leased vehicles. If you purchased your EV outright, you won't need Schedule A at all. The software should automatically skip that section when you indicate it was a purchase rather than a lease. I almost gave up and hired a tax preparer, but following this sequence finally unlocked the form and I was able to claim my full $7,500 credit. Don't give up - it's definitely there in FreeTaxUSA, just buried under several layers!