I've been carrying forward capital losses for years and an important tip is to KEEP DETAILED RECORDS of all your previous tax returns. The IRS randomly decided to question my loss carryforward in 2023 and I had to provide proof from returns going back to 2019. Was a total nightmare trying to find all those documents.

One thing I'd add to the excellent advice already given - make sure you understand the "wash sale" rules before filing those back returns. If you sold crypto or stocks at a loss and then bought the same or "substantially identical" securities within 30 days before or after the sale, the IRS considers it a wash sale and you can't claim the loss immediately. This is especially tricky with crypto since many people were buying/selling frequently during those volatile periods in 2021-2022. The wash sale rules can significantly reduce your claimable losses, so it's worth double-checking your transaction history before you file. Some of the tax software mentioned earlier should catch this automatically, but it's good to be aware of the rule going in.

Just wanted to add my experience from last month - I had both W-2 and freelance income and was super nervous about the appointment. Ended up bringing a huge folder with everything: original W-2s, all my 1099-NECs, bank statements, receipts, invoices, even my home office measurements (probably overkill lol). The agent was actually really nice and patient. She spent most of the time verifying my identity with the photo ID and Social Security card, then quickly flipped through my income documents. The whole thing took maybe 30 minutes. One tip: organize everything in chronological order beforehand - it makes the process smoother for both you and the agent. My refund was approved within a week! You got this!

Just wanted to echo what everyone's saying about bringing physical documents! I had my verification appointment two weeks ago and made the mistake of thinking I could use my phone for some things. The agent was polite but firm - they need to see and handle the actual documents. For self-employment, they asked to see my 1099s and a few sample invoices/receipts, but didn't dig too deep into my expense records. The key thing is having your Social Security card (not just knowing the number) and a valid photo ID. I'd also suggest calling ahead to confirm what time to arrive - some offices want you there 15 minutes early, others prefer you arrive exactly on time. The whole process was way less stressful than I expected once I had everything organized. Good luck with your appointment!

I went through this exact nightmare with Chase! The trust department insisted I was receiving income when I wasn't. Turned out the account was miscategorized in their system. Call and ask to speak specifically with the trust department (not just a regular banker). Request them to send you: 1. A copy of the trust documents they have on file 2. Documentation showing any distributions made to you 3. Written clarification of what type of beneficiary they have you classified as In my case, I was listed as a "current income beneficiary" when I should have been a "remainder beneficiary" - totally different tax implications! After 3 months of persistent calls and emails, they finally fixed it. And btw, you can absolutely file a complaint with the Office of the Comptroller of the Currency (OCC) if the bank is being unresponsive. That's what finally got the ball rolling for me.

This is a really complex situation, and I can see why you're confused! Based on what you've described, it sounds like there might be some miscommunication about what type of trust this is and what your actual status is as a beneficiary. A few things to consider: First, if you truly haven't received any distributions from the trust, then you likely don't have any current tax obligations to report. However, the bank requesting a W9 isn't necessarily wrong - they may need it for their compliance records even if you're not currently receiving taxable income. The distinction between "grantor beneficiary" and other types of beneficiaries is crucial here. In a grantor trust, the grantor (your grandfather) is typically responsible for all tax reporting, not the beneficiaries. But if you're actually a remainder or contingent beneficiary, that's a completely different situation. My recommendation would be to: 1. Request the complete trust document from whoever is managing it (trustee, executor, etc.) so you can understand your actual status 2. Consider providing the W9 to stop the hassle - it doesn't create tax liability if you're not receiving income 3. If the bank continues to insist you owe taxes on income you haven't received, escalate to their trust department supervisor You might also want to consult with a tax professional who specializes in trusts, as this could save you a lot of time and potential issues down the road. Trust taxation can be really tricky, and getting proper guidance upfront is usually worth the cost. Good luck sorting this out!

One thing nobody has mentioned yet - if you do end up giving more than the annual exclusion amount, it doesn't automatically mean you'll owe gift taxes. It just means you have to file a gift tax return (Form 709) and it counts against your lifetime estate and gift tax exclusion (which is over $13 million per person in 2025). So even if you accidentally go over the $18k per person annual limit, you probably won't actually pay any gift tax unless you've given away millions over your lifetime. The annual exclusion is just about whether you need to report the gift or not.

This is really helpful information! I'm in a similar situation with wanting to help my son with his first home purchase. One additional tip I learned from our family attorney - if you're doing the December/January strategy to maximize gifts across tax years, make sure the checks are actually deposited in the correct years. So if you write a check in late December but your daughter doesn't deposit it until January, the IRS considers that a gift in the year it was deposited (January), not when it was written. This could mess up your timing if you're trying to use both the 2025 and 2026 annual exclusions. We ended up doing electronic transfers to make sure the timing was crystal clear - $36K transferred on December 28th, 2024, and another $36K on January 3rd, 2025. Worked perfectly and gave our son the full $72K for his down payment!

Quick question about the mailing process - how do you actually submit 6 years worth of returns? Should I mail them all together or separately? I've heard mixed things.

Just to add another perspective on the 6-year requirement - while the IRS typically focuses on the last 6 years for compliance purposes, the specific years can depend on your situation. If you haven't filed any returns, they generally want 2018-2023 (counting back from when 2023 returns were due). However, if you filed some years but not others, they might focus on just the missing years. Also worth noting that if you had very low income (below the filing threshold) for certain years, you might not have been required to file at all - though you'd miss out on potential refunds like the Earned Income Tax Credit. Given that you mentioned mostly gig work around $25k annually, you were likely required to file (especially with self-employment income over $400), but you probably are due refunds for most years. I'd recommend starting with 2021-2023 since those are the only years you can still claim refunds for, then tackle the older years for compliance. Good luck with getting everything sorted before your mortgage application!