Just wanna share my experience - I had this EXACT same problem in Washington state last year!! That 10% withholding is such a trap. I thought I was being responsible by choosing to have taxes withheld from my unemployment but still ended up owing a ton. The real issue is that unemployment doesn't take into account your total annual income situation. For me, I had worked half the year making good money before being laid off, so combined with unemployment I was in a higher tax bracket than what the 10% covered. For anyone else facing this - consider setting aside some additional money beyond the 10% withholding if you can afford it. Better to have extra saved than to owe a bunch at tax time.

I'm dealing with a very similar situation right now! Made about $52k from my regular job before getting laid off in September, then collected unemployment for the rest of the year. Even with the 10% withholding, I still owe about $2,800 more in taxes. What really helped me understand it was realizing that the unemployment office has no idea what my other income was when they're calculating that 10% withholding. They're just taking a flat 10% without considering that my combined income ($52k + $28k unemployment = $80k total) puts me in a completely different tax bracket. The frustrating part is there's really no good way to avoid this unless you make quarterly estimated payments on top of the 10% withholding. I'm definitely going to do that if I'm ever on unemployment again. Live and learn I guess!

I ran into this exact same circular reference nightmare last year! What finally worked for me was treating it like an iterative process rather than trying to complete each form perfectly the first time through. Here's the step-by-step approach that broke the loop for me: 1. Start with your 1099-B and calculate your basic capital gain/loss (proceeds minus cost basis) 2. Put that preliminary amount on Schedule D Line 21 (or wherever your gain/loss lands) 3. Transfer that number to Form 1040 Line 13 4. Complete your Form 1040 through Line 44 using this preliminary capital gain 5. Now go back to Schedule D and use the tax information from Line 44 to complete any remaining calculations 6. If the final Schedule D number is different from your preliminary amount, update Form 1040 Line 13 and recalculate For a single stock sale like yours, the numbers usually don't change much between iterations, so you might only need to go through this process once or twice. The key insight is that these forms were designed assuming you'd use tax software that handles the circular references automatically - doing it by hand requires this back-and-forth approach. Don't let it drive you crazy - you're not missing something obvious, the forms really are designed this way!

I completely understand your frustration! I went through this exact same circular reference nightmare when I had to file my taxes after selling some stocks last year. It's like being stuck in a maze where every path leads back to where you started. The good news is that several people here have already given you great solutions. The iterative approach that Dmitry outlined is spot-on - you really do need to treat it like making multiple passes through the forms rather than trying to complete everything perfectly in one go. Here's what I learned from my experience: the key is to not overthink it. Start with the basic information you have (your 1099-B), make your best preliminary calculations, and then refine them as you work through the forms. The circular references exist because the tax code assumes everything will be calculated simultaneously (like tax software does), but when doing it by hand, you have to break it down into steps. One thing that really helped me was keeping track of which numbers I was using as "preliminary" versus "final" - I wrote little notes on my draft forms so I knew which calculations might need to be updated after completing the loop. Don't give up on the paper forms if that's your preference! Yes, it's more work than software, but it's totally doable once you understand the process. You've got this!

In case anyone else is reading this thread with a similar issue - make sure you check if your state has different rules for claiming refunds! Some states have longer statutes of limitations than the federal 3-year rule. For example, in Montana you have 5 years to claim a refund, and in South Carolina it's 3 years from the date you actually file (with no expiration if you never filed). I almost missed out on a state refund because I assumed the deadlines were the same as federal.

I'm really sorry to hear about your situation, Charity. Unfortunately, based on the information you've provided, it does appear that you've missed the deadline for claiming your 2019 refund. The three-year statute of limitations would have expired on July 15, 2023, since that was the COVID-extended due date for 2019 returns. However, I'd strongly encourage you to explore a couple of options before giving up completely: 1. **File the return anyway** - Even without getting the refund, filing will create an official record of your income and any withholding or estimated payments you made. This could be important for future financial needs. 2. **Check for any special circumstances** - While rare, there are some exceptions to the three-year rule for things like military service in combat zones, living in federally declared disaster areas, or certain other documented hardships. 3. **Consider state refunds** - As Hugo mentioned, some states have different deadlines than federal. Check your state's rules - you might still be eligible for a state refund even if the federal deadline has passed. 4. **Apply withholding to other years** - If you had tax withholding in 2019 and owe money for other tax years, you might be able to work with the IRS to apply those payments to years where you have a balance due. Don't beat yourself up too much - 2020 was an incredibly challenging year for everyone, and it's understandable that things slipped through the cracks.

You're absolutely right about the tax year choice! When you establish an estate, you can choose any 12-month period ending on the last day of any month as the estate's tax year. So if your mom passed away in February, you could choose a tax year ending February 28th, March 31st, December 31st, etc. This can be helpful for tax planning purposes. The key is that you make this election on the first Form 1041 you file. If you don't file a 1041 at all (because you're under the $600 threshold), then it doesn't matter. But if you do need to file, choosing the right tax year ending date can sometimes help with timing of income and deductions. For @Fiona Sand's situation with just the small bank account, she probably won't need to worry about this since it's unlikely to generate $600 in interest. But it's good information to know just in case!

I'm glad this discussion has been helpful! Just to add one more practical tip that saved me a lot of stress - keep detailed records of everything, even for a small estate like yours. I made a simple spreadsheet tracking the account balance on the date of death versus any interest earned after, along with copies of all the bank statements. Even though you probably won't need to file the 1041, having organized records made it so much easier when I had to provide documentation to close the estate account later. The bank wanted proof of the estate's income (or lack thereof) before they'd release the final distribution to me as beneficiary. Having everything documented upfront saved me from scrambling to recreate records months later. Also, don't forget to notify the bank that you have the EIN now - they'll need it to properly title the estate account and issue any tax documents if there is taxable interest earned.

Has anyone had their employer incorrectly include travel expenses for education in their W-2? My company added all my hotel and flight costs for a training program to my taxable income, and I think they're handling it wrong based on what people are saying here.

I'm dealing with a similar situation and wanted to share what I learned after consulting with a tax professional. The distinction between educational assistance benefits (Section 127) and business expense reimbursements is crucial here. For your $4900 course, if it's provided under your employer's qualified educational assistance program, it falls under the $5250 annual exclusion and won't be taxable income. The travel and lodging expenses are handled separately - they don't count toward the $5250 limit at all. If your employer reimburses travel expenses under an accountable plan (you provide receipts, return excess funds, and the expenses have a business connection), those reimbursements are typically not taxable and are treated as business expense reimbursements rather than educational benefits. The key question is whether your training maintains or improves skills for your current job. If yes, the travel expenses can qualify as deductible business expenses when reimbursed properly. If the education is to qualify you for a new career, the travel expenses would likely be taxable. I'd recommend checking with your HR department about how they're classifying these reimbursements on your W-2. Many employers mistakenly include travel reimbursements as taxable income when they should be treated as business expense reimbursements.