I've been through this exact EFTPS nightmare myself! After reading through all these suggestions, I wanted to add one more thing that helped me - check if your business structure changed between when you enrolled and when you're trying to log in. I had enrolled as a sole proprietor but then formed an LLC a few months later. Even though I was still using my SSN for taxes, the IRS had updated my records to show the LLC information, which created a mismatch with my original EFTPS enrollment that was still tied to my sole proprietorship. The customer service rep was able to see this discrepancy and update my EFTPS profile to match my current business status. It was such a relief after weeks of thinking I was going crazy with formatting issues! Also, definitely try the early morning call strategy - I got through at 7:15 AM in about 12 minutes versus the hour+ waits I experienced calling later in the day. The morning agents also seemed more patient and willing to dig deeper into the technical issues rather than just giving the standard "wait 2-3 weeks" response. For your immediate payment, Direct Pay is absolutely the way to go. But don't give up on EFTPS - once it works, scheduling all your quarterlies in January for the whole year is such a game changer for peace of mind!

I feel for you - EFTPS can be incredibly frustrating when you're just trying to pay your taxes on time! I had a similar issue last year where the system kept rejecting my information even though everything seemed correct. One thing that worked for me was making sure I was entering my EIN without any dashes or spaces - just the 9 digits straight through. Also, double-check that you're using your legal name exactly as it appears on your tax returns, not any shortened or nickname versions. For your immediate Q2 payment deadline, definitely go with IRS Direct Pay like others have mentioned. It's completely free and you don't need to register - just have your bank account info ready. You can find it at irs.gov/payments/direct-pay and select "Estimated Tax" as your payment type. While you're working on getting EFTPS sorted out, you might also want to try calling them super early in the morning (like 7 AM) when hold times are much shorter. I got through in about 15 minutes calling right when they opened versus hours later in the day. Don't give up on EFTPS completely though - once you get past this initial setup headache, being able to schedule all four quarterly payments at the beginning of the year is really convenient. The system just has some quirky formatting requirements that aren't obvious upfront.

This is such great information! I wish I had known about this years ago. I've been doing Instacart and DoorDash for about 18 months and have been religiously taking the standard deduction but completely ignoring my business expenses. One question though - what's the best way to track mileage going forward? I know some people use apps like MileIQ, but I'm wondering if there are simpler methods that are still IRS-compliant. Also, do you need to track every single trip or can you do periodic sampling and extrapolate? I'm definitely going to look into filing amended returns for last year. Even if I only drove 10,000 business miles, that's still potentially $6,000+ in deductions I missed out on. Thanks everyone for sharing your experiences!

This thread has been incredibly helpful! I'm another gig driver who's been making the same mistake for years. I drive for both DoorDash and Uber Eats and have been putting in about 20,000+ miles per year just for deliveries, but I've only been taking the standard deduction. Reading through everyone's experiences, it sounds like I could potentially be looking at thousands in missed deductions. The math is pretty shocking - at current mileage rates, that's over $13,000 per year in business expenses I haven't been claiming! I'm definitely going to start proper mileage tracking immediately and look into filing amended returns. Has anyone here had experience with multiple gig apps and how that affects the documentation? I'm wondering if I need separate mileage logs for each app or if one comprehensive business mileage log covers everything. Also, for those who mentioned using services like taxr.ai - did you feel comfortable uploading all your financial information to a third-party platform? I'm interested but also a bit cautious about data security with tax documents. Thanks to everyone for sharing their knowledge and experiences. This community is saving people thousands of dollars in overpaid taxes!

Has anyone used TurboTax for reporting the annual I-Bond election with an early redemption penalty? Does it handle this situation correctly or do I need to make manual adjustments?

This is a really helpful thread! I'm dealing with a similar situation with my teenager's I-Bonds. We elected annual reporting to take advantage of the kiddie tax exclusion, but I was confused about how to handle the 3-month penalty when we had to redeem early for unexpected expenses. Based on what everyone has shared here, it sounds like option 1 is definitely the way to go - only report the interest you actually get to keep. It makes sense that the penalty effectively means that interest was never earned in the first place. I'm curious though - does this same principle apply if you have multiple I-Bonds purchased at different times and you only redeem some of them early? Do you calculate the penalty impact on a bond-by-bond basis, or is there some other method for tracking which specific interest gets forfeited?

You'll want to ask your brokerage for what's usually called a "gift transfer form" or "securities gift documentation." Most major brokers have specific forms for this - for example, Fidelity calls it a "Gift of Securities Form," while Schwab uses an "Account Transfer Form" with a gift designation option. When you submit the request, make sure to specify that this is a gift transfer (not a sale) so they document it properly with the original cost basis. The paperwork should clearly show: 1) the transfer date, 2) that it's a gift (not a sale), 3) the original purchase date and cost basis of the securities, and 4) both your and your brother's identifying information. Most brokers will automatically generate the proper documentation, but it doesn't hurt to explicitly ask them to note it as a gift transfer in their records. This creates a clear paper trail that will be invaluable if there are ever any questions down the road about the cost basis or gift tax implications.

I've been following this thread and wanted to share my experience as someone who made the opposite choice - we kept our joint account and just dealt with the annual tax splitting. My sister and I have had a joint investment account for about 3 years now, and while the tax documentation is a bit more work each year, it's actually been manageable. We created a simple shared Google Sheet that tracks our contributions, dividends received, and any trades. Each December we run through it and calculate our respective portions of the 1099 income. I report everything on my return (since my SSN is primary), and she reports her portion on hers with a note explaining the allocation. Our tax preparer said this approach is totally fine as long as we're consistent and keep good records. The main advantage for us has been easier ongoing management - we can make investment decisions together and pool our buying power for certain positions. But reading through all these responses, I can definitely see how the separate account approach would be cleaner, especially if you're not actively managing investments together on an ongoing basis. Just wanted to offer the perspective that the joint account approach can work if you're willing to put in the annual documentation effort!

Did you check box A, B, C, D, or E on the form? If you're claiming any of the special conditions for waiver (like I had to when I had an unexpected wealth event mid-year), you need to attach an explanation letter along with the form. The IRS was super picky about having that documentation when I filed my 2210.

Based on everyone's responses, it sounds like the most likely issue is that you need to use 110% of your 2022 tax liability for line 5 since your AGI was over $150,000. But before you resubmit, I'd suggest double-checking a few things: 1. Make sure you're looking at the actual tax amount from line 16 of your 2022 Form 1040 (not line 24 which includes additional taxes) 2. Calculate both 90% of your 2023 tax ($13,423.50) AND 110% of your 2022 tax, then use whichever is smaller 3. If you haven't already, consider whether any of the waiver conditions apply to your situation (boxes A-E on the form) The good news is that once you get the calculation right, the IRS should process your refund relatively quickly. I went through something similar last year and it was frustrating, but getting that line 5 calculation correct based on your income level should resolve the issue.