Can someone explain if there's any difference in how Form 2555 should be filled out using TurboTax vs. H&R Block? I've been using TurboTax but it seems to be giving me weird results for my Housing Exclusion when I enter my Singapore housing expenses. I'm wondering if H&R Block handles Form 2555 better?

I've been through a similar situation with Form 2555 while working in South Korea, and I can confirm that TurboTax's interface for foreign income exclusions can be frustrating. Based on your circumstances, here are a few additional considerations: Since you left Japan on December 4th and your assignment was confirmed indefinite on October 18th, you're correct to only include the post-October 18th amounts for taxable fringe benefits. However, double-check that your 297 days calculation is accurate - make sure you're counting complete 24-hour periods outside the US, not partial days. For Line 21c (the rental car), if the vehicle was available for both business and personal use, you should include the full amount after October 18th ($1,700) as taxable income. The IRS generally treats employer-provided vehicles as taxable fringe benefits when the assignment exceeds one year. One thing I'd recommend: consider filing Form 2555 by paper rather than through TurboTax if the software keeps giving you strange results. The IRS processors are quite familiar with these forms, and sometimes the manual approach is more straightforward than fighting with software that doesn't handle complex expat situations well. Also, make sure you have documentation from your employer about the exact date your assignment status changed to indefinite. This will be crucial if the IRS has questions about your fringe benefit calculations.

Has anyone used TurboTax to handle the reporting for this kind of transaction? I'm dealing with this exact situation but not sure if regular tax software can handle it properly or if I need to hire a CPA.

I'd strongly recommend getting professional help for this type of transaction. While the strategy can work, there are several critical considerations that need to be handled correctly: 1. **Business Purpose Documentation**: The IRS will scrutinize whether your S-Corp has legitimate business purposes beyond just holding your former residence. You'll need to document these purposes clearly. 2. **Fair Market Value**: You must sell at true FMV - get a professional appraisal. The IRS can challenge related-party transactions if the price seems artificial. 3. **Corporate Formalities**: Your S-Corp needs to operate as a real business entity - separate bank accounts, proper meetings/resolutions, market-rate rent if you continue living there, etc. 4. **Mortgage Complications**: As others mentioned, most residential mortgages have due-on-sale clauses. You'll likely need commercial financing for the S-Corp. 5. **State-Specific Issues**: Property tax reassessment, transfer taxes, and state-level reporting requirements vary significantly by location. The potential benefits can be substantial if you have significant appreciation, but the compliance requirements are complex. A qualified CPA experienced with real estate transactions and S-Corp structures is essential - don't try to navigate this alone with tax software.

As someone who's dealt with this exact scenario multiple times, I can confirm that the wash sale situation with RSUs is incredibly frustrating. Here's what I've learned from experience: The key insight is that the sell-to-cover transaction happens automatically and you typically can't control which specific shares are used. Most brokers use FIFO, so if you have shares with adjusted cost basis, there's a good chance some of them were used in the sell-to-cover. What I do now is contact my broker immediately after each vesting event to get a detailed breakdown of: 1. Which shares were actually sold for tax withholding 2. The specific cost basis of those shares 3. Which of my remaining shares have wash sale adjustments This information isn't always obvious in the standard account statements, but most brokers can provide it if you ask specifically. One thing that really helped was setting up automatic alerts 35 days before each vesting date to remind myself not to sell any company stock at a loss. It's not perfect given trading window restrictions, but it's prevented most of the wash sale headaches. Also worth noting - if you're in a high tax bracket, sometimes it's actually better to just hold the RSUs long-term rather than trying to optimize around these wash sale rules. The long-term capital gains treatment can be more valuable than the short-term tax loss harvesting, especially when you factor in the time and complexity involved.

I've been through this exact situation and found that the most practical approach is to work backwards from your Form 1099-B to understand what actually happened. Your broker is required to report the wash sale adjustments, and this will show you exactly which shares had adjusted basis and whether any of those were used in the sell-to-cover transaction. In my experience with similar RSU programs, the 240 shares sold for taxes are typically processed as a separate transaction from your 360 remaining shares, but the wash sale adjustment applies to specific tax lots based on FIFO ordering (unless you've changed your default method). Here's what I'd recommend: Contact your broker's tax department and ask for a "wash sale detail report" for the transactions around your Sep 28 vesting. This will show you exactly which of your remaining shares carry the $8/share cost basis adjustment. One key thing I learned - you don't necessarily need to sell all 360 shares to claim the loss. You only need to sell the specific 250 shares (or whatever subset) that have the adjusted basis. But identifying which ones those are requires getting the detailed lot-level information from your broker. Given the complexity and your trading window restrictions, you might also want to consider whether the tax benefit is worth the administrative headache. Sometimes simplifying your approach (like holding RSUs long-term or avoiding loss harvesting near vesting dates) provides better peace of mind even if it's not perfectly tax-optimized.

You're totally fine to file Schedule C without any formal business registration! I've been doing freelance web development for 3 years now and started the same way - just picking up projects here and there with no LLC or business license. The IRS doesn't care about your business structure, they just want you to report the income you earned. Your $8,500 in earnings definitely qualifies as self-employment income, and those business expenses you mentioned (laptop, software, home office) are legitimate deductions as long as you use them for your graphic design work. Just make sure you can prove the business use percentage if the IRS ever asks. One tip: since you made over $400 in self-employment income, you'll owe self-employment tax (about 15.3%) on top of regular income tax, so don't forget to account for that when planning your payment. But the business deductions will help offset some of that burden.

I had the exact same concern when I started doing freelance consulting work! You definitely don't need a business license to file Schedule C - the IRS recognizes you as a sole proprietor automatically once you start earning income from self-employment activities. One thing that helped me feel more confident was organizing all my documentation before filing. Since you mentioned keeping records of payments through Venmo and direct transfers, I'd recommend downloading those transaction histories and creating a simple spreadsheet showing dates, clients, amounts, and brief descriptions of work performed. For expenses, keep receipts and note the business purpose. The home office deduction can be valuable, but make sure you understand the requirements - the space needs to be used regularly AND exclusively for business. If you work at your kitchen table sometimes, that won't qualify, but if you have a dedicated desk area only used for graphic design work, you're good to go. Also, don't forget you'll need to pay quarterly estimated taxes going forward if you expect to make similar or more income this year. The IRS expects self-employed folks to pay as they go rather than waiting until year-end. Good luck with your filing!

This thread has been incredibly helpful! I've been dealing with a similar RSU confusion for months. Just to add one more perspective - if you're still having trouble reconciling everything, consider requesting a detailed breakdown from your company's stock plan administrator (not just the brokerage). My HR department was able to provide me with a report showing exactly how much RSU income was added to each paycheck throughout the year, along with the corresponding withholding amounts. This made it much easier to match up with my W-2 and verify that everything was reported correctly. Also, for anyone using tax software like TurboTax or FreeTaxUSA, make sure you're entering RSU sales correctly - the software often tries to treat them like regular stock purchases where you paid cash, but since RSUs were "free" to you, your cost basis is the vesting date fair market value (which was already taxed as income). Getting this wrong can definitely lead to double taxation!

Great discussion everyone! I wanted to add something that might help others avoid the confusion I experienced. When you receive RSUs, think of it as two completely separate tax events: 1) **Vesting Event**: When RSUs vest, it's treated as regular compensation income (like getting a bonus). Your employer reports this on your W-2 and withholds taxes just like they do from your regular paycheck. This is where those "missing" taxes are - they're combined with all your other payroll withholding in Box 2 of your W-2. 2) **Sale Event**: When you sell the vested shares, it's a separate capital gains transaction reported on Form 1099-B from your brokerage. Since you're selling immediately after vesting, there's usually little to no capital gain/loss. The key insight that finally clicked for me: the tax withholding happens during the vesting event (handled by your employer's payroll), not during the sale event (handled by the brokerage). That's why you won't see the withholding on any documents from Morgan Stanley - they're just executing the sale transactions. If you're still confused, definitely check your paystubs from vesting periods and look for any supplemental tax documents your employer might provide specifically for equity compensation.