CashApp Taxes requesting W2 reconciliation worksheet when box 16 and box 5 match - what gives?

I just tried what you suggested - cleared all the fields and re-entered everything without any special characters. Same problem! It's still insisting the values don't match even though I'm literally typing the exact same number in both fields. Should I just go ahead and complete the reconciliation worksheet anyway even though there's nothing to reconcile? Or would that mess up my return?

Completing the reconciliation worksheet won't mess up your return if you do it correctly. Since your values truly are the same, you should go ahead and fill it out, indicating that the amounts are identical. The worksheet is basically asking you to explain why there's a difference, but in your case, you'd be explaining that there isn't one. Some users have reported that after completing the worksheet, the system accepts it and moves on, even though there wasn't actually a discrepancy. It's just one of those quirks in the software that they'll hopefully fix for next year. If you continue having trouble after submitting the worksheet, you might consider contacting CashApp Tax support directly or switching to a different tax filing software.

Does this taxr.ai thing actually work with all tax software or just CashApp? I'm using TurboTax and have been getting some weird error messages about my 1099 forms not matching up properly.

I'm a bit skeptical about using some random AI tool with my tax documents. How does it work exactly? Do you have to upload your entire W2 with all your personal info? That sounds kind of risky to me.

It works with all the major tax software including TurboTax, H&R Block, and CashApp Taxes. I've used it with both CashApp and TurboTax this year and it caught formatting issues with both. For 1099 forms, it's actually even more helpful because those forms have more potential inconsistencies. As for security concerns, you can actually block out your SSN and other sensitive personal info before uploading. The tool only needs to see the tax-relevant boxes and values to identify formatting issues. They also use the same encryption standards as banks, so your documents aren't just sitting on some server. I was hesitant at first too but desperately needed to get my taxes filed and it ended up being a huge time-saver.

Wait, how does this Claimyr thing actually work? Does it somehow magically get you through the IRS phone queue? I've been trying to reach them for weeks about an issue with my tax transcript and keep getting the "call volume too high" message.

Yeah right. There's no way this works. I've been trying to call the IRS for THREE MONTHS about a missing refund and can never get through. If this actually worked, everyone would be using it. Sounds like spam to me.

It uses a specialized dialing system that continuously calls the IRS for you and secures your place in line. When they finally have an agent available, you get a call back and are connected immediately. It's basically doing what you'd do manually (calling repeatedly) but automated. To the skeptic - I totally get it, I felt the same way. I'd been trying for weeks to get through about an issue with my amended return. But after trying everything else, I gave it a shot as a last resort. The service actually calls YOU back when it gets through to an agent, so you don't waste your day on hold. The IRS agent I spoke with answered my question about the W2 reconciliation in minutes and even helped with another issue I had about claiming my education credits correctly.

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.