As a newcomer to this community, I just want to say how incredibly helpful this entire discussion has been! I was also completely stressed about my 2021 amendment deadline, thinking I had to rush everything by this April. Learning that I actually have until April 2025 is such a huge relief. What really impresses me is how this thread has evolved from a simple deadline question into this comprehensive guide for handling amendments properly. The systematic approach everyone has developed here - starting with thorough document gathering, then using tools like taxr.ai for a complete review, followed by Claimyr for IRS contact if needed - is exactly what someone like me needed. I'm particularly motivated by all the success stories - Alice finding $650, Myles discovering $1,200 including that Recovery Rebate Credit, and so many people uncovering home office deductions they'd forgotten about. I also worked remotely for part of 2021 and completely overlooked that possibility. Gabriel's audit warning is definitely noted - I'll make sure to be thorough and verify everything else on my return is accurate before filing. But seeing how methodical and successful everyone has been gives me confidence this can be done safely. Thank you all for sharing such detailed experiences and creating this amazing roadmap. You've turned what felt like an overwhelming crisis into something I can actually handle properly. Time to start gathering those 2021 documents!

This entire discussion has been incredibly enlightening! As someone who's been putting off dealing with my 2021 tax situation, I can't express how relieved I am to learn about the April 2025 deadline instead of thinking I had to rush everything by this month. What's really impressive is how this thread has developed into such a comprehensive resource. The systematic approach everyone has shared - starting with thorough document gathering, using taxr.ai for a complete review, then Claimyr for IRS contact when needed - gives me a clear roadmap I never would have figured out on my own. I'm particularly intrigued by all the success stories about unexpected deductions. Like many others here, I transitioned to remote work in 2021 and completely forgot about potential home office deductions. Plus reading about the Recovery Rebate Credit issues has me wondering if I handled my stimulus payments correctly. Gabriel's audit warning is definitely something I'll keep in mind as I move forward. It sounds like the key is being thorough upfront and making sure everything else on the return is solid before filing any amendments. Thanks to everyone who's shared their experiences and resources here. You've transformed what felt like a stressful emergency into a manageable project I can actually approach methodically. Time to start digging through those 2021 documents and following the proven strategy you've all outlined!

Has anyone used TurboTax or similar software to handle these loss carryovers from closed businesses? I'm in a similar situation and wondering if the mainstream tax software can correctly handle these situations or if it's worth paying a CPA one last time.

As someone who recently went through a similar situation with closed business entities, I'd strongly recommend getting professional help one more time to ensure you handle these carryovers correctly. The rules around passive loss disposition and QBI carryforwards can be tricky, and making mistakes could cost you significant tax benefits or trigger an audit. If you're determined to DIY, make sure you have all your prior year tax documents showing the original sources of these losses. You'll need to trace back to the Forms 8582, 8582-CR, and Form 8995-A from previous years to properly calculate what becomes deductible versus what carries forward. The passive losses should indeed become fully deductible in the year of complete disposition, but you'll need to prove the businesses were completely closed and disposed of. Keep documentation like final bank statements showing zero balances, state dissolution certificates, and any asset sale records. For the QBI loss carryforward, unfortunately that's likely going to remain unused unless you generate qualifying business income in the future. There's no mechanism to convert unused QBI losses to ordinary deductions when you permanently exit business activities.

Double check your 1099-R coding carefully! When I took a distribution for my first home purchase, Vanguard initially coded mine as a regular early distribution (Code 1) instead of a first-time homebuyer distribution (Code J). I had to call them and have them issue a corrected 1099-R. Also remember that the first-time homebuyer exception is limited to $10,000 lifetime across all IRAs, so even if you used $8,000 now, you only have $2,000 left for this exception in the future. Just something to keep in mind.

The $10,000 first-time homebuyer limit applies per individual, not per household! So if you and your husband both qualify as first-time homebuyers (haven't owned a home in the past 2 years), you can each withdraw up to $10,000 from your respective IRAs penalty-free - that's potentially $20,000 total for your down payment. Just make sure you both meet the first-time buyer definition and that your IRA custodians properly code the distributions with Code J on your 1099-Rs. Also remember this limit is lifetime across all your IRAs, so if either of you has used this exception before, that reduces your available amount. The same contribution vs. earnings rules apply to both of you - if you're withdrawing amounts equal to or less than your total Roth contributions, those should be tax-free regardless of the 5-year rule or your age.

Don't forget state implications when you move! I moved my business from Texas to Pennsylvania and got hit with all kinds of unexpected tax issues. Since ur moving states make sure ur looking at Michigan's rules about recognizing previous business losses from another state. Some states are super weird about it.

One thing to consider with your woodworking business restart - the IRS actually views legitimate business interruptions due to family emergencies (like your wife's illness) more favorably than businesses that just fail to turn a profit. This works in your favor for the hobby loss analysis. Since you're essentially starting fresh in Michigan, treat this as a business pivot rather than just a restart. Document your market research for the new location, any adjustments to your business model, networking efforts, and how you're leveraging your existing equipment investment in the new market. The IRS wants to see that you're making businesslike decisions to improve profitability. Also, regarding the LLC question - while the legal structure itself doesn't guarantee legitimacy, operating through an LLC with proper business formalities (separate bank accounts, business insurance, formal record keeping) can strengthen your overall business case. Just make sure you're actually following through with professional business practices, not just the paperwork.

Has anyone else had problems with their HSA provider charging extra fees for contributions made outside of payroll? After my layoff, my HSA administrator started hitting me with $2 transaction fees for each direct deposit I made. Seems like a ripoff!

One thing to keep in mind is that when you make direct HSA contributions (not through payroll), you'll miss out on the FICA tax savings you would have gotten with payroll deductions. Payroll HSA contributions avoid both income tax AND the 7.65% FICA tax, while direct contributions only avoid income tax. That said, the tax deduction is still substantial! Just make sure to keep good records of all your contributions throughout the year. I recommend setting up automatic monthly transfers to your HSA so you don't forget to max it out, especially while job hunting when finances might be tight. Also, since you mentioned your former employer is covering health insurance for 2 years, double-check that your plan still qualifies as a High Deductible Health Plan. Sometimes employer-sponsored continuation coverage can have different terms than the original plan.