Another approach that worked for me last tax season - check if H&R Block has a "Review" or "Summary" section before you file. Many tax software programs generate a comprehensive review document that includes all your entries in a more accessible format. In H&R Block, look for something like "Review Your Return" or "Tax Summary" - this often creates a consolidated view of all your forms and schedules. Sometimes this review format is more copy-friendly than the individual input screens. Also, if you're comfortable with it, you might try using browser developer tools if you're using the online version of H&R Block. Press F12, go to the Console tab, and sometimes you can access the underlying data that way. It's a bit technical but I've seen people extract form data this way when normal copy functions are blocked. The combination of these suggestions from everyone should definitely save you from having to manually type all 51 transactions!

Just wanted to share another potential workaround that saved me last year - if you have access to the actual 1099-B forms from your broker (Fidelity in your case), you might be able to download them directly from their website in a more Excel-friendly format. Most major brokerages like Fidelity, Schwab, etc. allow you to download your tax documents as PDFs, and some even offer CSV or Excel exports of your transaction history. Log into your Fidelity account and look for a "Tax Documents" or "Year-End Documents" section. The advantage is that this data comes straight from the source and won't have any transcription errors that might occur from copying between software programs. You can then use this to verify what you've entered in H&R Block rather than trying to extract it from the tax software. I found my broker's export was actually more detailed than what the tax software showed, which helped me catch a few small discrepancies. Worth checking before going through all the screenshot/OCR steps!

I've been following a similar strategy for about 2 years now, overpaying by roughly $18K annually. One thing that's given me peace of mind is working with a tax professional who helped me establish a defensible estimation methodology. What we do is create quarterly projections that account for variable income scenarios - like potential bonuses, freelance work, or investment gains that might materialize. I document these projections each quarter, showing how I arrived at my estimated payment amounts. Sometimes the income materializes, sometimes it doesn't, but the important thing is having a reasonable basis for each payment. The processing fees (around 1.9%) are definitely worth it when you're hitting signup bonuses that can be 15-20% returns in just a few months. Just make sure you're not putting all your overpayments on one card or making it too obvious that you're manufactured spending. My advice would be to treat this as legitimate tax planning first, credit card optimization second. Keep good records, vary your amounts somewhat year to year, and make sure you can articulate why your estimates led to overpayments if ever asked. The IRS isn't going to penalize you for being conservative with your tax planning.

I've been considering this strategy myself and appreciate all the insights here. One additional angle I'd suggest is looking at safe harbor rules for estimated taxes. If you pay either 100% of last year's tax liability or 110% (for higher income earners), you're automatically safe from underpayment penalties regardless of how much you actually owe. This gives you a legitimate framework for "conservative" estimates that could result in systematic overpayments. You could base your estimated payments on projections that ensure you hit these safe harbor thresholds, and if your actual income ends up lower, the overpayment becomes a natural byproduct of following IRS safe harbor guidelines. The beauty of this approach is that you're literally following an IRS-recommended strategy for avoiding penalties. It's hard for them to question a methodology they explicitly endorse, even if it results in consistent overpayments when combined with credit card optimization. Just make sure to document your safe harbor calculations each year to show you're following established tax planning principles rather than arbitrary overpayment amounts.

Have you tried checking your account transcript on the IRS website? This can sometimes show the status of abatement requests before you get the official letter. Just go to irs.gov and look for "Get Transcript Online." The transcript will show if they've processed any adjustments to your account.

I went through almost the exact same situation with my daughter's account last year. The good news is that you absolutely will get your money back if the abatement is approved - paying early actually works in your favor since it stops additional penalties from accumulating. For minor children's filing requirements, the IRS typically considers the parents' compliance history for first-time penalty abatement requests. Since this was an honest mistake about a filing requirement you hadn't encountered before (kiddie tax rules are confusing!), and assuming you have a clean filing history, your chances are pretty good. One tip: definitely check your account transcript on irs.gov periodically. Sometimes you'll see the adjustment processed there before you receive any official correspondence. Look for transaction codes that indicate penalty adjustments - it can give you peace of mind while waiting for the formal decision letter. The timeline really varies by service center, but 8-16 weeks is typical. Since your accountant has gone MIA, you might want to consider following up yourself if you don't hear anything by early February. You can always call the practitioner priority line if needed, though expect long hold times.

Just an FYI - I'm an enrolled agent and we've seen this exact issue with multiple tax software packages this year. It seems to be a software implementation problem rather than an actual change in IRS policy. The Form 5329 instructions (even the 2023 version) still clearly state you can request a waiver by entering "RC" and attaching an explanation. Nothing in SECURE Act 2.0 changed this procedure. If you're using tax software that won't let you properly code the waiver, you might consider switching software or as someone else suggested, paper filing with the appropriate modifications.

As someone who's dealt with similar Form 5329 penalty waiver issues, I can confirm that the IRS hasn't changed their policy on this. You're absolutely right to be confused by H&R Block's approach - their software seems to have a bug or misinterpretation of the rules. I encountered this exact same problem last year with excess IRA contributions. After getting frustrated with my tax software insisting I pay upfront, I called the IRS directly (took forever to get through) and spoke with a specialist who confirmed that the waiver process hasn't changed. You still enter "RC" in the penalty amount box on Form 5329 and attach your reasonable cause statement. The specialist also mentioned they've been getting a lot of calls about this because several tax software companies seem to have implemented incorrect logic around Form 5329 penalties. She specifically said that SECURE Act 2.0 didn't change the penalty waiver procedures at all. My suggestion would be to either switch to software that handles this correctly (like FreeTaxUSA as you mentioned), or if you're committed to H&R Block, use their software to prepare everything else but paper file with manual corrections to Form 5329. Don't let software bugs force you into paying penalties you legitimately don't owe!

Thank you all for the helpful advice! I'm feeling much less panicked now. Based on everyone's suggestions, I'm going to: 1. Complete Form 3520 today and mail it certified mail tomorrow morning 2. Include a brief explanation letter with my SSN and tax year info 3. Keep it simple - acknowledge the oversight and emphasize I'm filing immediately upon discovery Maya, your experience with being 2 weeks late and having no penalty is really reassuring. I'm also going to look into both taxr.ai and Claimyr in case I need additional help or need to speak with the IRS directly. One quick question - should I reference the specific foreign trust details in my explanation letter, or just keep it general about discovering the filing requirement? I don't want to overcomplicate things but also want to be transparent. Really appreciate this community helping a stressed taxpayer out!

Just wanted to chime in as someone who's dealt with Form 3520 issues before. Your plan sounds excellent - certified mail with return receipt is absolutely the way to go, and keeping the explanation letter brief but clear is smart. One thing I'd add: make sure you're filling out the form completely and accurately. The IRS is pretty particular about Form 3520, so double-check all the sections that apply to your situation. If you're unsure about any part, it might be worth having a tax professional review it before you send it in. Also, keep copies of everything - the completed form, your explanation letter, the certified mail receipt, and the return receipt when it comes back. Having that paper trail will be invaluable if any questions come up later. You're handling this the right way by addressing it immediately. Most people in your situation who file promptly with a reasonable explanation don't face penalties. The IRS tends to be more understanding when you show good faith effort to comply once you realize the requirement.