Has anyone here actually e-filed state returns separately? Which tax software actually lets you do this easily? I tried it with H&R Block last year and it was a nightmare - the software kept insisting I file federal and both states together.

I went through this exact situation two years ago when I moved from Wisconsin to Florida mid-year. Here's what I learned from my CPA: You absolutely CAN file your state returns at different times, but there's a critical detail everyone seems to be missing - you need to be very careful about your part-year resident status on each return. For Colorado, you'll file as a part-year resident and only pay Colorado tax on the income you earned while living there (January through July). For Arizona, you'll also file as a part-year resident for the income earned there (August through December). The key is making sure your total income across both state returns matches what you'll report on your federal return. If you're missing Arizona documents, you could estimate based on your pay stubs, but honestly it's safer to wait until you have everything. One more thing - check if Colorado has any special rules about when part-year residents must file. Some states require you to file by the federal deadline regardless of when you moved.

I went through this exact same situation last year when I proposed! The good news is that everyone here is giving you solid advice - your fiancée won't owe any taxes on the ring, and you probably won't either unless you're already close to that $13+ million lifetime exemption (which most of us definitely aren't!). Just wanted to add one practical tip: when you do file Form 709 to report the gift over $18,000, make sure you get a proper appraisal of the ring's fair market value rather than just using what you paid for it. Sometimes the actual value can be different from the purchase price, especially if you got a good deal or bought from a high-markup retailer. The IRS wants the fair market value, not necessarily your receipt amount. Also, don't stress too much about the paperwork - Form 709 is actually pretty straightforward for a simple gift like this. You've got until April 15th of the year after you give the gift to file it. Good luck with the proposal!

Great question about the appraisal timing! You don't need to get it done immediately when you purchase the ring - you have until you file Form 709 (by April 15th of the year after the gift) to obtain the appraisal. However, I'd recommend getting it done relatively soon after purchase while the market conditions are still similar. For IRS purposes, you'll want a certified appraisal from a qualified appraiser rather than just something from the jewelry store. Look for appraisers who are certified by organizations like the American Society of Appraisers (ASA) or the American Appraisal Society. The jewelry store appraisal might work for insurance purposes, but for tax reporting you want someone independent who specializes in valuations. One tip: when you get the appraisal, make sure they know it's for gift tax purposes specifically, as this can affect how they approach the valuation methodology. The fair market value should reflect what a willing buyer would pay a willing seller in the current market.

Has anyone tried calling the Taxpayer Advocate Service about these old health insurance penalties? I've heard they sometimes help with IRS issues when you're facing hardship or can't get resolution through normal channels.

I went through something very similar with a 2017 health insurance penalty notice last year. The key thing to understand is that the IRS is definitely still collecting on these, despite what people said back then about being able to ignore them. When I got my CP71H notice, I was also confused about why my refunds hadn't been offset. I learned that the IRS has specific rules about which debts they can offset refunds for, and the health insurance penalty has some restrictions around that process. My advice would be to act quickly on this. The interest keeps accruing daily, and while $711 might not seem like a huge amount, it can grow pretty fast. I ended up calling the IRS (eventually got through after multiple attempts) and they were actually quite reasonable about setting up a payment plan. The agent explained that they're working through a backlog of these penalties systematically, which is why some people are just now getting notices for 2017 tax years. Don't assume this will just go away - the 10-year collection period gives them plenty of time to pursue it. If you can afford to pay it in full, that's probably your best bet. If not, the installment agreement option is definitely worth exploring.

Just wanted to chime in that the IRS online account only shows the last few years - completely normal. Had a similar panic when I could only see back to 2020. For peace of mind until you can call, check if you have any old tax prep software files on your computer. Sometimes they save copies of previous returns. Also, check your email - if your ex e-filed, there might be confirmation emails from TurboTax or whatever software you used.

I went through almost the exact same situation after my divorce two years ago! The stress of not knowing what was actually filed is horrible, but you're taking the right steps. A few things that helped me piece together my tax history: 1. Check if you have any old copies of tax software on shared computers - I found TurboTax files going back years that my ex had saved locally 2. Look through old bank statements for IRS refund deposits or payments - this can confirm which years returns were actually filed 3. If you have old pay stubs, compare your year-end totals to what should have been reported - this helped me spot a year where income wasn't properly reported The most important thing is getting those transcripts from the IRS to see your official filing history. Don't stress too much about the online account only showing recent years - that's completely normal. For your 2022 return, you can still e-file without the prior year AGI by using the PIN option or indicating you didn't file the previous year. The IRS will process it and you can sort out any discrepancies later. You've got this! It's overwhelming now but once you have the facts from the IRS, you'll know exactly what needs to be fixed.

Has anyone actually been audited for this type of issue? I accidentally had a similar situation last year but just left it alone. My contribution was coded for the wrong year but I took the deduction anyway on my taxes. It's been 18 months and nothing has happened. Maybe I'm living on borrowed time but wondering if the IRS actually cross-references these?

I went through almost the exact same situation last year with my SEP IRA! The key thing to remember is that this is an administrative error, not a true recharacterization issue. Since you made the contribution before the 4/15/24 deadline with clear intent for 2023, you have strong grounds to get this fixed. First, gather all your documentation - any emails or forms where you specified this was for 2023, bank records showing the timing, etc. Contact Fidelity immediately and explain the situation. They can reach out to your previous institution on your behalf to request corrected Form 5498 reporting. If the old advisor won't cooperate, you can file Form 4852 with the IRS as a substitute for the incorrect Form 5498. Include a detailed explanation and all supporting documentation showing your intent. The October deadline mainly applies to true recharacterizations between IRA types, but administrative error corrections can sometimes be handled even after that date. Don't amend your 2023 return yet - fight to get the coding fixed first. You legitimately made a 2023 contribution and deserve to keep that deduction. Time is of the essence though, so start making those calls tomorrow morning!