I went through almost the exact same situation last year with my father's inherited IRA. The key thing that saved me was understanding that the 1099-R reporting doesn't automatically reflect rollovers - you have to manually indicate this on your tax return. Here's what worked for me: On Form 1040, I reported both 1099-R amounts on the "IRA distributions" line, but then on the "taxable amount" line, I only included the actual disbursement ($12,500 in your case). I attached a statement explaining that $215,000 was a direct rollover to an inherited IRA and therefore not taxable. The IRS accepted this without question. Make sure you keep detailed records of the rollover transaction - account statements showing the money going from the original IRA directly into your new beneficiary IRA. This documentation is crucial if you ever get audited. One tip: if you used different financial institutions for the original and new IRAs, the transfer might have been coded as a distribution + contribution rather than a direct rollover, which could explain why you're seeing it as taxable income. This can usually be corrected with proper documentation on your return.

I had a very similar situation with my grandmother's IRA last year and want to share what I learned through the process. The confusion you're experiencing is unfortunately very common because the 1099-R forms don't automatically show the full picture of what happened with your money. You're absolutely right that you shouldn't be taxed on both the transfer AND the disbursement - that would indeed be double taxation. The $215,000 that went directly into your beneficiary IRA should not be taxable income since it remained in a qualified retirement account. Here's what I discovered: You need to look carefully at both 1099-R forms. The first one (for the $215,000) should have a distribution code in Box 7 - likely code 4 since it's a death benefit. However, it probably doesn't have a rollover code like G or H, which is why it's appearing as fully taxable. When you file your return, you'll report the full amount from both 1099-Rs on the "IRA distributions" line, but on the "taxable amount" line, you should only include the $12,500 that you actually received as cash. The difference ($215,000) should be reported as a non-taxable rollover. I strongly recommend keeping detailed documentation of the transfer - bank statements, account opening documents for the beneficiary IRA, and any correspondence with the financial institutions. If the transfer happened between different companies, make sure you have proof it was completed within the required timeframe. The IRS sees this type of situation frequently, so as long as you document it properly on your return, it should process without issues. Consider consulting with a tax professional if you're unsure about the specific forms to complete, as inherited IRA rules can be quite complex.

I went through this exact same situation a couple years ago when a small consulting firm I worked for suddenly shut down. What ultimately worked for me was contacting the bank where I had direct deposit set up. I called my bank's customer service and explained that I needed employer information for tax purposes. They were able to pull up the ACH transaction details from my old direct deposits, which included not just the company name but also their routing information and business account details. While they couldn't give me the EIN directly, they provided the exact legal business name and the bank where the company had their account. I then called that bank (it was a small local bank) and spoke with a business banker who was familiar with the account. Since the business had closed, they were willing to confirm the EIN for tax purposes - apparently this is a pretty common request they get. The whole process took about a week but it was much faster than waiting for government agencies to respond. Plus, banks tend to have very accurate business information since they need it for all their compliance requirements. Just another option to add to all the great suggestions here!

Just wanted to add one more suggestion that worked for a friend of mine in a similar situation - check if the company had any business licenses or permits that might still be searchable online. Many cities and counties maintain databases of business licenses, contractor permits, or professional licenses that include the business's federal tax ID. For example, if it was a restaurant, they would have had health department permits. If it was a construction company, they'd have contractor licenses. Even something like a business license or sales tax permit from the city/county might include the EIN in the records. These local government databases are often overlooked but can be goldmines of information. The permits usually stay in the system even after a business closes, and they're typically searchable by business name. Worth checking your local city and county websites to see what business databases they maintain. Also, one thing I learned from my own experience - don't forget to check if they had any professional licenses or certifications specific to their industry. These are often maintained at the state level and require accurate tax information for renewal and reporting purposes.

Just wanted to add from personal experience - my now-spouse and I were in almost this exact situation 2 years ago. We decided to get legally married but maintained separate households because of kids and custody schedules. We had to switch from both filing HOH to married filing jointly, and honestly, our tax situation actually improved slightly. The higher standard deduction and more favorable tax brackets for joint filers offset what we lost from HOH status. Plus, tax preparation was so much simpler doing one joint return instead of two separate ones. Sometimes the tax code actually works in your favor!

This is a really common misconception! Once you're legally married, the IRS considers you married for the entire tax year, regardless of when during the year you got married or your living arrangements. You'll need to choose between Married Filing Jointly or Married Filing Separately - you can't both file as Head of Household. The "considered unmarried" exception that allows married people to file HOH has very strict requirements, including living completely apart from your spouse for the last 6 months of the tax year. Since you mentioned spending kid-free weekends together, this would disqualify you from that exception. However, I'd strongly recommend running the numbers before making any decisions! With your income levels and dependents, Married Filing Jointly might actually save you money compared to your current HOH filings. The joint standard deduction is essentially double the single amount, and you might benefit from more favorable tax brackets and other married filing benefits. Many couples are surprised to find that the "marriage penalty" isn't as bad as they expected, especially with similar incomes.

One thing nobody mentioned - get ready for a MEGA tax bill if this is your first year doing freelance work. I was shocked when I owed over $2k on just $10k of freelance income. Now I put 25% of every payment into a separate savings account for taxes. Save yourselves the panic I went through lol!

This thread has been super helpful! I'm actually in a similar situation but with a twist - I made around $12k on Fiverr but also did some direct client work outside the platform that went straight to my PayPal. From what I'm reading here, I'll need to report both income sources separately, right? The Fiverr income will be on their 1099, but for the direct PayPal payments I'll need to calculate that myself since those clients probably won't send me 1099s (most were small amounts under $600 each). Also want to echo what others said about setting aside tax money - I learned this the hard way with some side gig income a few years back. That quarterly payment reminder is gold! Better to be prepared than scrambling to find thousands of dollars at tax time.

I went through this exact situation with Amazon Flex last year! Here's what fixed it for me: 1. Clear your browser cache completely 2. Try using a different browser altogether (Firefox worked when Chrome failed) 3. Disable any ad blockers or privacy extensions 4. Make sure you're using the exact same email address as your Flex account 5. If all else fails, contact Amazon Flex support through the app Such a relief when I finally got in! If you're really stuck, you can also request your wage and income transcript directly from the IRS which will show what Amazon reported for you.

Hey Zoe! I totally feel your stress about this - tax deadline anxiety is real! I've been doing gig work for a few years and ran into similar issues. A few things that might help: First, definitely try Ryan's suggestion about the Stripe portal - that's actually how I accessed mine last year when the main Amazon portal was being glitchy. Also, Benjamin's tip about using the mobile app instead of the website is spot on - I've noticed the app tends to be more reliable. If you still can't access it, don't panic! You can absolutely file your taxes without the official 1099 form. Just gather all your payment records from the Amazon Flex app (go to Earnings > Payment History) and add up your total for 2023. The IRS cares more about you reporting the income accurately than having the physical form. One more thing since you mentioned caring for your mom - make sure to look into the Credit for Caring if she qualifies as your dependent. And if you're using your car for deliveries, don't forget to track those business miles for deductions! You've got this! 💪