That's interesting but I only have one W2 job, so I don't think that's the issue for me. Though that's good to know for the future if I ever have multiple employers. Did you end up just filling out the reconciliation worksheet to explain the legitimate difference?

Yes, I completed the worksheet and explained the legitimate difference. For me, the difference was because I worked in two states during the year (relocated mid-year), so my box 16 state wages were split between two states while my box 5 Medicare wages were the total for the entire year. The reconciliation worksheet allows you to explain these discrepancies, and CashApp accepted my explanation without any issues. Once I submitted it, I was able to continue with my filing. In your case, since there shouldn't be a difference, just clearly state that the values are identical and that there appears to be a system error causing the false flag.

Yeah, CashApp Taxes has been buggy this season. For your student loan interest issue, make sure you're entering your 1098-E in the income section and not the deductions section. Counter-intuitive, I know, but that's how their system is set up. If that doesn't work, try entering the information again in a private/incognito browser window - sometimes their web cache causes issues.

Thanks for mentioning H&R Block! Did you have any issues with their import feature? I tried using CSV imports with TurboTax and it kept failing with my large number of transactions. Also, did you still have to manually verify each transaction after import or does it handle batches well?

The import feature works well with properly formatted CSVs, but you need to follow their template exactly. I had no issues with about 450 transactions last year, though I've heard mixed results from others with very large transaction counts (1000+). You don't need to manually verify each transaction after import, which is a huge timesaver. H&R Block handles batch processing well and groups similar transactions appropriately. The software still does some verification checks, but it's usually just confirming the total amounts rather than line-by-line review. Make sure your CSV includes all the required fields (date acquired, date sold, proceeds, cost basis, etc.) to avoid validation errors.

That's brutal! Did you at least get a tracking number or some kind of confirmation that they received your paperwork? I'm worried about mailing in hundreds of pages and them just getting lost in some IRS warehouse.

Banks are required by law to keep those records! Ask to speak to a supervisor in their tax document department, not just a regular customer service rep. If they still refuse, remind them that per IRS regulations they MUST provide you with copies of tax documents for at least 3 years. If all else fails, you can try filing Form 4506-T with the IRS to get wage and income transcripts that might show the IRA contributions even if you don't have the bank's forms. I had to do this when my credit union "lost" my 5498 records during a system update.

Thanks for this advice! I called again today and specifically asked for the tax document department instead of regular customer service. They still gave me trouble but when I mentioned the IRS regulations about maintaining records, their tone changed completely. They're sending me copies of all my 5498 forms from the last 4 years. I had no idea about Form 4506-T either, that's super helpful as a backup option. I'm starting to feel like we need a complete guide for dealing with banks that "lose" or mess up IRA contribution records!

This is really important info, thank you! Our letter arrived yesterday, so I'm guessing our 90-day clock is already ticking. Should we hire a tax attorney to help with the Tax Court petition if we can't get this resolved quickly? I'm worried about messing up the paperwork and losing our right to challenge this.

This is such an important point! My mortgage broker never explained this difference to me. Is there an easy way to figure out which portions of my loans count as acquisition debt versus home equity debt?

There's no automatic or easy way unfortunately - you need to track the use of the funds. Acquisition debt is only money borrowed to buy, build, or substantially improve your home. If you refinanced at some point, it gets even more complicated because you have to track the original acquisition debt. For example, if you had a $400k mortgage to buy your home, then later did a cash-out refi for $500k and used that extra $100k for something unrelated to the home (like college tuition), only the $400k portion remains deductible acquisition debt. It's a huge pain to track but worth figuring out before the IRS questions it.

That's a great point. I'm in New Jersey with high property taxes and the SALT limitation basically makes my mortgage interest deduction worth a lot less. I actually ended up just taking the standard deduction last year even with a huge mortgage because of this.

Did you get any kind of confirmation number or anything when they approved it? I just submitted my request and realized I forgot to ask for some kind of reference number.

This is really helpful, thanks! Is there a difference in success rates between calling vs writing a letter for the FTA request?

In my experience, calling is generally faster if you can actually get through to someone. You'll often get an immediate decision during the call. The agent can check your compliance history on the spot and approve the FTA right then. Letters take much longer due to IRS processing backlogs - sometimes 8-12 weeks or more. However, the success rate is probably about the same either way. The FTA criteria are pretty straightforward, and if you qualify, you should get approved regardless of which method you use. One advantage of writing is that you have documentation of exactly what you requested. If you call, make sure to take detailed notes of who you spoke with, when, and what they said.