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Has anyone else had issues with the IRS questioning their physical presence test documentation when splitting the 330 days across two calendar years? I did something similar last year and the IRS sent me a letter requesting additional proof beyond my travel records.
I had this happen to me! What worked was sending them a complete travel log with entry/exit dates, along with copies of passport stamps, flight itineraries, and a signed letter from my commanding officer confirming my deployment dates. I also included credit card statements showing purchases in foreign countries on specific dates. The more documentation layers you can provide, the better. For days spent in countries that don't stamp passports, I included hotel receipts as well. The IRS accepted all this as proof.
Great question about the FEIE and differential pay! As someone who's navigated similar military tax situations, I can confirm that your differential pay should qualify for the Foreign Earned Income Exclusion as long as you meet the physical presence test. A few key points to consider: 1. **Timing flexibility**: You don't need to complete all 330 days in 2023. You can use any consecutive 12-month period, so starting mid-February 2023 and going through mid-February 2024 could work perfectly for your situation. 2. **Documentation is crucial**: Keep detailed records of every day you're outside the US - deployment orders, passport stamps, travel receipts, etc. The IRS can be thorough when reviewing FEIE claims, especially for military personnel with complex situations. 3. **Coordinate with your employer**: Make sure your civilian employer understands how they should be handling withholding on your differential pay. Some companies automatically adjust for FEIE, others don't. 4. **Consider state taxes**: Don't forget that some states don't recognize the FEIE, so you might owe state taxes even if the income is federally exempt. The proration calculation across tax years can get complex, so you might want to consult with a tax professional who specializes in military situations to make sure you're maximizing your benefits correctly.
I'd recommend a slightly different approach that worked for me. Instead of selling the same stock in both accounts, consider selling the taxable account position for the tax loss, then immediately exchanging the IRA position for something different but similar (like a competitor in the same industry). This way you're not holding the "substantially identical" security in your IRA anymore, which should allow you to claim the tax loss. And since there are no tax consequences for selling at a loss in the IRA anyway, you're not giving anything up. Just make sure whatever you exchange into isn't considered "substantially identical" to the original security. This approach let me harvest the tax loss without being completely out of the market for 31 days.
That's a smart workaround! Would this also work if the positions were in a taxable account and a 401k instead of an IRA? My company 401k has limited investment options.
This is a really common situation that catches a lot of people off guard! You're absolutely right to be concerned about the wash sale implications. Unfortunately, since you purchased the same stock in your IRA on January 15th (just 7 days after your taxable account purchase), selling the taxable position on February 18th would indeed trigger a disallowed wash sale. The IRS looks at all your accounts - including retirement accounts - when applying the wash sale rule. Here's what I'd suggest: If you want to claim the tax loss, you'll need to sell both positions and wait at least 31 days before repurchasing the same stock in either account. Since you mentioned the stock isn't recovering anyway, this might actually work in your favor from an investment perspective. One thing to keep in mind - your broker's 1099-B will likely NOT flag this as a wash sale because most brokers only track wash sales within the same account. It's your responsibility to identify and properly adjust for cross-account wash sales when filing your return. If you're looking to stay invested in the same sector, consider selling both positions and immediately buying a similar but not identical stock (like a competitor or sector ETF) to avoid being completely out of the market during the 31-day waiting period.
A quick tip if you do take this job - I make a deduction worksheet for all 1099 work. Track mileage between work sites (not commuting), any supplies you buy, portion of phone/internet if you use them for work, professional subscriptions, software, etc. Keep ALL receipts, take photos of them with your phone right away (they fade!). Also track any home office space if you do some work from home.
This is good advice! I use an app called Everlance to track all my business expenses and mileage. It's like $8/month but worth it because it categorizes everything for tax time. Saved me hours of sorting through receipts.
Just wanted to add another perspective here - I was in almost the exact same situation last year (required to work in their office, set schedule, but given a W9). After doing some research, I decided to take the job but immediately started documenting everything that showed I was really an employee, not a contractor. Things like: emails about required work hours, office policies I had to follow, equipment they provided, training materials, etc. After 6 months, I filed Form SS-8 with the IRS to get an official determination on my classification. The IRS ruled I was misclassified as a contractor and should have been an employee. Long story short - I got a refund for the extra self-employment taxes I paid, and my employer had to reclassify me and pay their portion of payroll taxes going forward. It was a bit of a process but totally worth it financially. If you take this job, document everything that shows they control how, when, and where you work. It could save you thousands later if you need to challenge the classification.
This is really helpful to know! How long did the SS-8 process take from filing to getting a determination? And did your employer give you any pushback when the IRS ruled in your favor, or did they comply pretty quickly? I'm wondering if it's worth the potential workplace tension while the case is pending.
One thing nobody has mentioned is that Missouri has some specific state-level considerations for S-corps that differ from some other states. I'm a MO agent too, and our state taxes S-corps a bit differently than sole props. Make sure whoever you work with is familiar with MO specifically. Also, did your CPA mention anything about how the 20% QBI deduction factors into this decision? That's another big piece of the S-corp vs LLC analysis that might affect your choice.
Great point about Missouri-specific considerations! The QBI deduction interaction is crucial and often overlooked. For S-corps, the QBI deduction applies to your business income MINUS the W-2 wages you pay yourself. So if you're paying yourself a high salary (like that 70% some CPAs recommend), you're reducing the income eligible for the 20% QBI deduction. This creates an interesting balance - you want your salary high enough to avoid IRS scrutiny but not so high that you lose significant QBI benefits. In many cases, this actually supports the 50-60% salary range that others have mentioned here. Missouri also doesn't conform to federal S-corp elections automatically, so you need to make a separate state election. Plus MO has that franchise tax for S-corps that LLCs don't pay. These state-level costs should definitely factor into your breakeven analysis. I'd recommend running the numbers with both federal AND Missouri tax implications included. The total picture might be different than just looking at federal savings alone.
Marcus Williams
Has anyone calculated how much time they're losing on this? I've spent exactly 3.5 hours over 2 days trying to access my transcripts. Need them to verify my $4,750 refund status. Called IRS exactly 8 times with average wait time of 47 minutes before disconnecting. This is costing people real money in wasted time.
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Kennedy Morrison
ā¢Shouldn't the IRS extend filing deadlines when their own systems prevent us from accessing necessary information? How are we supposed to verify our information when we can't even see our transcripts?
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Wesley Hallow
ā¢I finally got in on April 12th at around 2:15 AM! Such a relief. I was worried I wouldn't be able to get the documentation I needed for my mortgage application due on April 15th.
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Ava Harris
I'm experiencing the same issue! Been trying to access my transcripts since yesterday morning for a loan application and keep getting timed out. This is really concerning since I have a deadline coming up. Has anyone tried using the mobile app instead of the website? Sometimes different platforms have different server loads. Also wondering if there's an official IRS Twitter account or status page where they post about these outages?
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