Mine was stuck on processing forever until I used taxr.ai - showed me there was an ID verification hold I didnt know about. Fixed it and got my refund in a week!

Been waiting 3 weeks on my Maryland refund too! The "processing" status is so vague - wish they'd give us more details about what's actually happening. At least with federal returns you can see more specific codes and stages. Maryland's system feels like a black box sometimes 😤

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.

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.

Can someone explain in simple terms how to actually calculate the IRC 1341 credit? My mom received Social Security benefits for my dad after he passed, but then had to repay them the following year when they determined she wasn't eligible. I'm trying to help her figure out if this credit applies and how to calculate it.

I went through a similar situation with my husband's employer overpayment situation last year. One thing I learned that might help Emily - make sure you have the IRC 1341 credit calculation worksheet clearly documented and attached to your response to the IRS. We initially just referenced Publication 525 in our filing, but the IRS examiner wasn't familiar with the specific calculation method. When we resubmitted with the actual worksheet showing step-by-step how we calculated the credit amount (comparing the tax liability with and without the repaid income), they processed it much faster. Also, if your brother-in-law's employer has an HR department or payroll company, try to get a letter from them that specifically uses the words "overpayment" and "paid in error" rather than just "repayment requested." The IRS seems to want very clear language establishing that the original payment was incorrect, not just that money was requested back for other reasons. The 6-month timeline isn't unusual for this type of credit review, but having the right documentation should speed things up considerably.

One thing nobody has mentioned - double check if your old plan has any special requirements for rollovers. Some plans require you to get spousal consent forms notarized before they'll process a rollover, even if you're not married! It's ridiculous but happened to me. Also, make sure your old 401k doesn't have any outstanding loans. If it does, you'll need to pay those off before they'll process any kind of rollover.

I went through this exact same frustration last year! Your former employer is definitely confusing the processes. The W-4R is for taxable distributions, but a direct rollover isn't a distribution to you - it's a transfer between qualified plans. Here's what finally worked for me: I called my NEW 401k provider first and asked them to initiate the rollover from their end. They sent me their "incoming rollover" forms and handled all the communication with my old plan administrator. This completely bypassed my former employer's HR department, who honestly didn't seem to understand the difference between direct and indirect rollovers. The key phrase you want to use is "trustee-to-trustee transfer" - this is the technical term that plan administrators understand. Also, make sure you have your new plan's acceptance letter or documentation showing they'll accept the rollover. If you're still getting pushback, you can reference IRS Code Section 401(a)(31), which specifically gives participants the right to elect direct rollovers. Good luck!

This is exactly the kind of situation where having clear documentation makes all the difference. I went through something similar with my S-Corp two years ago when we had late state tax payments due to a banking error. The key thing I learned is to always request a detailed breakdown from the taxing authority showing exactly how much is penalty versus interest - sometimes they lump it together on the initial notice. What really helped me was creating a simple spreadsheet tracking each payment with columns for: Date, Total Amount Paid, Penalty Portion (non-deductible), Interest Portion (deductible), and Supporting Document Reference. This made it super easy for my CPA to handle the deductions properly and gave me peace of mind during our subsequent IRS correspondence audit. Also, don't forget that if you're making estimated tax payments going forward, getting those right can help you avoid this whole mess in the future. The safe harbor rules for S-Corps can be a lifesaver for avoiding underpayment penalties.

I just went through this exact scenario with my S-Corp last month! The confusion is totally understandable because the notices from state tax authorities often don't clearly separate these amounts. Here's what I learned from my experience: The interest portion IS deductible as a business expense on your S-Corp return (Form 1120-S), while penalties are not. The key is getting proper documentation that breaks down exactly how much of your payment was penalty versus interest. I had to call our state tax department and specifically request a detailed statement showing the breakdown. For reporting, the interest goes on Line 13 (Interest) of Form 1120-S. Make sure to attach a statement explaining what the interest relates to - something like "Interest paid on late state tax payment for [tax year]" along with the date and amount. One thing that caught me off guard: if you pay the penalty and interest in a different tax year than when the original tax was due, you deduct the interest in the year you actually paid it, not when the underlying tax was originally due. Hope this helps while you're waiting for your accountant to get back! The good news is this is a pretty straightforward issue once you have the proper documentation.