Another option if you filed with a tax preparer: call them! I lost all my docs in a computer crash and my accountant had copies of everything going back 7 years. Most preparers keep records for at least 3-5 years by law.

Just to add a timeline perspective - I requested transcripts by mail using Form 4506-T and it took exactly 12 days to arrive. Online was instant but I needed the mailed copy for some reason I cant remember. Just FYI if ur on a deadline!

Has anybody else tried using business expenses they don't have receipts for? I'm in a similar situation (got about $32k on 1099-NEC) and used some of my apartment for work, plus my personal laptop, but don't have specific receipts for those. FreeTaxUSA let me enter them, but now I'm nervous.

The $4.5k-$5k tax bill is definitely normal for your situation! As others mentioned, self-employment tax is the big killer - you're paying both sides of Social Security and Medicare taxes (about 15.3%) plus regular income tax. A few things that might help going forward: 1. **Track everything better this year** - get a separate business checking account and run all business expenses through it. Makes record-keeping so much easier. 2. **Home office deduction** - if you use part of your living space exclusively for work, you can deduct that percentage of rent/utilities. Even a corner of your bedroom counts if it's your dedicated workspace. 3. **Equipment depreciation** - that laptop, desk, chair, etc. can be depreciated over several years rather than deducted all at once, which might spread out the benefit. 4. **Mileage** - track any driving for work (client meetings, picking up supplies, etc.) at 65.5 cents per mile for 2023. The phone at 50% business use sounds totally reasonable. I'd also look into whether any of your college courses relate to your work - sometimes continuing education can be deductible. Don't stress too much about this year's bill - it's a harsh welcome to self-employment taxes, but now you know what to expect and can plan accordingly!

Pro tip: If you're calling about an extension, make sure you're using the right number. The IRS has different lines for different issues.

I've dealt with this exact same issue! What worked for me was using a landline instead of a cell phone - the connection seemed more stable. Also, make sure you're not on speakerphone or using Bluetooth headphones, as those can cause connection issues. Another trick is to press a random number key every few minutes during the hold time to keep the line "active" - sometimes the system drops calls it thinks are inactive. Hope this helps and you can finally get through! 🤞

Have you considered composite returns? Some states allow partnerships to file a single composite return on behalf of all nonresident partners, which can dramatically simplify your filing burden. Not all states offer this option, but many do. The requirements vary by state, but essentially the partnership pays tax on behalf of the partners for that state's sourced income. It's typically a flat rate and while sometimes higher than individual rates, the administrative convenience can be worth it. I manage several partnerships with similar multi-state issues, and we've reduced our state filings by about 60% using composite returns where available.

I run into this issue every year with my investment partnerships. Here's my practical approach that's worked for 15+ years: 1. Always file in your home state plus any state with income over $1,000 2. File in "aggressive" states regardless of amount (CA, NY, MA, NJ, IL) 3. For states with income under $500, I keep documentation showing the amount but don't file unless they contact me 4. For amounts between $500-$1,000, I make a case-by-case decision based on the state's reputation Following this approach, I've only had two states ever contact me about non-filing (Oregon and Connecticut), and in both cases, the penalties were minimal compared to the preparation costs I saved over the years. Just know that technically you're supposed to file everywhere you have income, so this approach does have some risk. But from a practical standpoint, the tax departments in many states are too understaffed to pursue very small amounts.

Anyone know what the realistic chances are of actually getting a whistleblower award? My brother-in-law claims he got like 15% of what the IRS collected after his report, but that sounds like BS to me.

Based on my experience working in tax compliance, your evidence sounds pretty solid for a Form 211 submission. Emails discussing "keeping it off the books" combined with screenshots of accounting discrepancies can be very compelling evidence - the IRS looks for patterns that show intentional tax evasion rather than just mistakes. A few key points for your documentation: - Organize everything chronologically to show the pattern over time - Include dates, amounts, and context for each piece of evidence - Your $450K estimate is fine - show your methodology for how you arrived at that figure - Keep detailed notes about those overheard conversations (who, when, where, what was said) The IRS doesn't expect you to have perfect proof - that's their job to investigate. Your role is providing substantial information that gives them a starting point. From what you've described, you definitely have enough to warrant filing. Just make sure you're only using information you had legitimate access to through your normal job duties to avoid any retaliation issues. Good luck with your submission!