


Ask the community...
Another thing to consider - the timing of when you sell might matter for tax purposes. If you've held the Bitcoin for over a year, you'll qualify for long-term capital gains rates, which are typically lower than short-term rates. For 2025, long-term capital gains are taxed at 0%, 15%, or 20% depending on your income bracket, while short-term gains are taxed as ordinary income (potentially much higher). So if some of your brother's Bitcoin investments were made less than a year ago, it might be worth waiting until they cross that one-year threshold before selling.
Also worth noting that the cost basis method you choose can make a huge difference in crypto taxes. FIFO (first in, first out) vs. specific identification can result in totally different tax outcomes.
I'm dealing with a similar situation with my sister's crypto investments, and from what I've learned, you're actually in a pretty good position with that documentation you mentioned having since 2019. One thing that hasn't been mentioned yet - make sure you're calculating the cost basis correctly for each of your brother's purchases. Since he's been making weekly $65 investments, you'll need to track the purchase price of Bitcoin at each transaction date to determine his individual cost basis for each "lot" of Bitcoin purchased. This becomes important because when he sells, you'll need to determine which specific Bitcoin purchases are being sold (FIFO, LIFO, or specific identification method) to calculate the actual capital gains or losses accurately. Also, since you mentioned you're not currently working, be aware that even though the Bitcoin sale will appear on your tax return, the actual tax liability should really be your brother's responsibility. You might want to have a clear agreement with him about covering not just the taxes owed, but also any additional tax preparation costs since this complicates your return significantly. The joint vs. separate filing question is tricky, but as others mentioned, joint filing is almost always more beneficial. The key is making sure your brother understands he needs to reimburse you for the full tax impact on your household.
This is really helpful advice about tracking the cost basis for each weekly purchase! I hadn't thought about how complicated it would be to calculate gains/losses for each individual $65 Bitcoin purchase over the years. Do you know if there are any tools or software that can help with this kind of detailed cost basis tracking? With weekly purchases since 2019, that's going to be a lot of individual transactions to sort through manually. I'm worried I might make mistakes calculating everything by hand. Also, you mentioned having a clear agreement with my brother about covering tax costs - should this be something in writing? I want to make sure we're both protected if the IRS has questions later.
Absolutely get that agreement in writing! Even though it's your brother, having documentation protects both of you. I'd recommend a simple written agreement that outlines: 1) He owns the beneficial interest in the Bitcoin, 2) You're acting as custodian, 3) He's responsible for all tax liabilities from the sale, and 4) He'll reimburse you for any additional tax prep costs. For cost basis tracking, most major crypto tax software like CoinTracker, Koinly, or even TurboTax's crypto features can handle this if you can export your transaction history from the exchange. They'll automatically calculate gains/losses using your preferred method (FIFO/LIFO/specific ID) and generate the forms you need. Since you have those Venmo records showing exactly when he sent money, you should be able to match those dates to your Bitcoin purchases and create a clear trail. The software will do the heavy lifting on calculating the cost basis for each lot.
I'm going through almost the exact same thing right now! Filed my Form 5329 about 7 weeks ago for a missed RMD (also due to advisor issues - mine moved firms and the transition got messy). Got that same frustratingly vague acknowledgment letter that tells you absolutely nothing useful. Reading through all these responses is actually making me feel much better about the situation. It sounds like this is just how the IRS operates with Form 5329 submissions - they send the generic "we got it" letter first, then take their sweet time processing everything before sending any kind of final resolution. The timeline everyone's mentioning (8-12 weeks) seems pretty consistent across different people's experiences. I'm trying to be patient but it's hard when you're wondering if you're going to get hit with additional penalties or complications. At least I know I'm not the only one dealing with this kind of confusing communication from the IRS!
Logan, I'm glad you found the responses here helpful! It's such a relief to know that others have gone through this exact same confusing process. I was starting to wonder if I had done something wrong when I got that vague letter, but it sounds like the IRS just has a really standard (and unfortunately uninformative) way of handling these Form 5329 submissions. The advisor transition issues seem to be pretty common too - it's frustrating how these kinds of changes can slip through the cracks and lead to missed RMDs. At least we're both being proactive about fixing the situation rather than just ignoring it and hoping it goes away! I'm at about 6-7 weeks myself, so we're probably on similar timelines. Fingers crossed we both get our resolution letters soon and can put this whole stressful situation behind us. Thanks for sharing your experience - it helps to know I'm not alone in this waiting game!
I've been following this thread closely because I'm dealing with a very similar situation - missed RMD due to a communication breakdown with my financial institution, filed Form 5329 with penalty payment about 5 weeks ago, and got that same maddeningly vague acknowledgment letter. What I'm finding really valuable here is seeing the consistent timeline everyone is reporting (8-12 weeks) and hearing that paying the penalty upfront along with an explanation letter generally leads to successful resolution. It's also reassuring to know that these generic acknowledgment letters are completely normal and don't indicate any problems with your submission. One thing I wanted to add for anyone else reading this - I learned that it's worth keeping detailed records of everything during this process. I'm maintaining a simple log with dates of when I submitted the form, when I received the acknowledgment letter, when my check was cashed, etc. If I do need to call the IRS later or if any issues arise, having all those details readily available will make the conversation much more productive. Thanks to everyone who shared their experiences here - it's really helping reduce the anxiety of waiting for the IRS to finish processing everything!
Dylan, that's such a smart approach keeping detailed records throughout this process! I wish I had thought to do that from the beginning. I'm now scrambling to remember exactly when I sent everything in versus when I got the acknowledgment letter back. Your point about having all the details ready for a potential IRS call is really good advice. I've been putting off calling them because of the horror stories about wait times, but if I do end up needing to check on status later, having precise dates and reference numbers will definitely make that conversation more efficient. It's also really comforting to see how many people in this thread have dealt with similar advisor/financial institution communication breakdowns. Makes me feel less like I was completely irresponsible and more like this is just one of those things that can happen when there are transitions in financial services. The important thing is that we're all taking steps to fix it properly rather than ignoring the problem. I'm at about the same timeline as you (5-6 weeks), so hopefully we'll both see resolution in the next month or so. Thanks for adding your perspective to this really helpful discussion!
I went through this exact same frustration last year with a $3,200 Form 941X refund. Unfortunately, as others have mentioned, there's no direct deposit option for these - it's paper checks only, which is ridiculous in 2025! What I learned from calling the IRS multiple times (before I knew about services like Claimyr) is that 941X refunds go through a completely different processing system than individual tax refunds. The employment tax division handles these manually, and their systems aren't connected to the electronic refund infrastructure. One tip that might help with cash flow while you wait - if you have other quarterly tax payments coming up, you can potentially apply future 941X refunds as credits toward those payments instead of requesting a refund check. You'd need to contact the IRS to set this up, but it can help with the timing if you have upcoming tax liabilities. Just make sure your accounting team is aware of any credits you arrange so they don't double-pay. The whole process is outdated but unfortunately we're stuck with it for now. I'd budget for at least 8-12 weeks realistically, despite what the official timelines say.
That's really helpful info about applying refunds as credits to future payments! I had no idea that was even an option. Our next quarterly payment isn't due until July, but if we could apply our $4,300 refund toward that instead of waiting for a check, it would definitely help with cash flow planning. Do you happen to know what department at the IRS handles setting up those credit arrangements? I assume it's not something you can do online through the business portal. Also, is there a minimum refund amount required to do this, or can any 941X refund be converted to a credit? I'm getting tired of feeling like we're stuck in the stone age with all these paper-based processes when everything else in business has gone digital!
I feel your pain on the direct deposit issue! We went through the same thing with our 941X refund last year - ended up waiting 13 weeks for a $5,100 check while our cash flow suffered. One thing I wish I had known earlier is that you can actually request expedited processing if your business is experiencing financial hardship. You have to call the Practitioner Priority Service line (if you have a POA with your tax pro) or the regular business line and explain your situation. They don't advertise this option, but I've heard of cases where they've moved 941X refunds through faster when there's genuine hardship involved. Also, double-check that you didn't accidentally check any boxes on the 941X that might slow down processing. We made the mistake of checking the "amended return may affect prior or subsequent periods" box when it wasn't necessary, which apparently triggers additional manual review. The whole system definitely needs to be modernized - it's frustrating that we can file and pay taxes electronically but still have to wait for paper checks like it's 1985!
Nobody's mentioned the education exclusion for savings bonds! If you use the I-Bond proceeds for qualified education expenses, you might be able to exclude the interest from your income completely. It's subject to income limits, but worth looking into if you or a dependent has education expenses.
That's a good point but I think it only applies to EE bonds and I bonds if they were issued after 1989 and you're at least 24 years old when you bought them. Plus there's income limits like you mentioned. But definitely worth checking if you qualify!
You're right about those requirements. To clarify: the bonds must be issued after 1989, the bond owner must be at least 24 years old when the bonds were purchased, and they must be used for qualified education expenses for yourself, your spouse, or a dependent. The income limits for 2024 start phasing out at modified adjusted gross income of $91,850 for single filers and $137,800 for joint returns. It's completely phased out at $106,850 and $167,800 respectively. And this only applies to the interest portion, not the penalty discussion.
This is such a common source of confusion! I went through the exact same thing last year when I had to cash in some I-Bonds early for an emergency expense. The key difference that helped me understand it is this: with CDs, you actually earn ALL the interest throughout the term, but then the bank takes some back as a penalty. That's why it shows up as income and then gets deducted. With I-Bonds, the Treasury literally just stops paying you interest for those last 3 months - you never "earn" it in the first place. Think of it like this: if you work 10 hours but your boss docks 2 hours pay as a penalty, you can deduct that penalty. But if you only work 8 hours to begin with, there's nothing to deduct. That's essentially what's happening with I-Bonds vs CDs. One thing to double-check though - make sure you're reporting the I-Bond interest correctly. If you didn't get a 1099-INT from Treasury (they only send them if you redeem $600+ in a year), you'll need to calculate the interest yourself using the redemption value minus what you originally paid.
That's a really helpful analogy with the work hours! I think I finally get it now. So basically with my I-Bonds, I should just report whatever interest I actually received (the redemption value minus what I paid), and there's no separate penalty line to worry about. Just to make sure I understand - if I bought $1,000 in I-Bonds and redeemed them for $1,050 after 2 years, I'd report $50 as interest income and that's it? No other forms or deductions related to the "lost" 3 months of interest?
Malik Davis
I went through this exact same situation a couple years ago when I started taking personal finance seriously! That initial shock of seeing your refund drop is really jarring, but you're absolutely making the right financial moves. One thing that helped me was thinking about it differently - that $520 difference in your refund represents roughly $2,364 in interest income you earned (assuming you're in the 22% bracket). So even after taxes, you still came out ahead by about $1,844 compared to keeping that money in a regular checking account earning nothing! For next year, I'd recommend starting with the IRS Tax Withholding Estimator in January to get a baseline, then checking it again around June when you have a clearer picture of your actual interest earnings. Interest rates can change throughout the year, so your projections might need adjusting. Also consider that if your savings continue to grow (which sounds like the plan!), your interest income will keep increasing, so you'll want to revisit your withholding annually. The key is just staying on top of it rather than letting it surprise you again. You've got this!
0 coins
Yara Nassar
ā¢This is such a helpful way to frame it! I never thought about calculating backwards from the tax impact to see how much interest I actually earned. That really puts it in perspective - earning nearly $2,400 in interest is definitely worth dealing with a slightly more complex tax situation. Your point about revisiting the withholding annually is spot on. I think part of my stress was thinking I needed to get this perfect and never think about it again, but it makes sense that as my savings grow and interest rates potentially change, I'll need to adjust accordingly. Thanks for the encouragement! It's reassuring to hear from someone who went through the same learning curve.
0 coins
Zara Khan
This is exactly what happened to me when I first opened my HYSA! The key thing to remember is that you're still way ahead financially - that $520 reduction in your refund likely represents around $2,300+ in interest income you earned (depending on your tax bracket), so you netted roughly $1,800 more than if you'd kept it in a regular savings account. For withholding adjustments, I'd recommend using the IRS Tax Withholding Estimator tool mid-year once you have a better sense of your actual interest earnings. HYSA rates can fluctuate, so your January estimate might be off by year-end. A simple approach: take your current quarterly interest earnings, multiply by 4 to get an annual estimate, then multiply that by your marginal tax rate (probably 22% based on your situation) to see how much extra tax you'll owe. Divide that by your number of paychecks per year and add that amount to line 4(c) on your W-4. Don't let this discourage you from the HYSA - it's still the smart move! You're just learning how to manage the tax side of building wealth, which is a good problem to have.
0 coins
Aurora Lacasse
ā¢This is really helpful advice! I'm also new to dealing with HYSA interest on my taxes and was worried I was doing something wrong financially. Your calculation method makes it so much clearer - I can actually see that I'm still coming out way ahead even after the tax impact. One question: when you mention HYSA rates can fluctuate, how often do you typically revisit your W-4 withholding? Is it worth adjusting if rates change by like 0.25% during the year, or do you just wait until the next tax season to make bigger adjustments? I'm trying to find the balance between staying on top of it and not over-managing every little change.
0 coins